manager wants to buy underwear for employees — and wants to approve it first

A reader writes:

A friend of mine recently told me that her boss takes her and a coworker shopping a couple of times a year. Sounds nice, huh? Apparently the shopping experience is done together and the boss directs the employees to what they can look for (shoes, handbag, etc.) and then upon her approval, she’ll buy the items and they are on their merry way. She presents it as a treat, but I think she just wants them dressed more professionally. My friend always looks nice, but she isn’t really the “suit and dress” type. She prefers slacks and a blouse. She does not meet with any clients; she sits behind a desk most of the day, so I don’t know why this lady is such a whack job about the clothes.

Recently, the boss could not go and told the gals to visit a particular department store and find dresses, suits, handbags, shoes, bras and underwear. They were told to place the items on hold and that she would go the next day and review the items and buy them upon her inspection. My friend felt uncomfortable having her boss “review and accept” bras and panties and therefore did not place any on hold. The next day, the boss complained about her not choosing the undergarments and complained that she had to go to the lingerie department searching for the items “on hold” – annoyed that nothing was there. When my friend told her she simply didn’t need any new undergarments, she was scolded for not following the rules. The boss did, however, allow the rest of the items and brought them in for her.

Personally, if I want to treat my staff to something special, I take them to lunch and toss them a gift card (or cash) and a smile. When I heard this story, I thought it was kind of inappropriate. Almost borderline sexual harassment. I had suggested she decline the next shopping adventure and hope for a gift card instead. But apparently the boss doesn’t want the employees spending the money on their kids or anyone else but them. And obviously doesn’t want them wearing anything she doesn’t feel is worthy. What are your thoughts?

What?! Whoa. No.

This is completely weird and inappropriate.

And I have so many questions: Has she ever rejected an item they proposed buying? Did she give them any particular guidance on the underwear piece of this excursion, and if so, what was was it?!  What on earth did they say to her when she told them to pick out bras and underwear?

In any case, if it was just her taking them shopping, it would be a generous gesture, if a bit boundary-crossing. Throw in needing to get her approval for the shoes and handbags and so forth, and it’s pretty controlling, but it’s more weird than outrageous.

But directing them to purchase bras and underwear? Insisting that she approve those bras and underwear first? Chastising them when they don’t put lingerie on hold for her to look at?



If she were a man, this would be obvious perviness. She doesn’t get a pass on that simply for being a woman, but I suppose it’s also possible that it’s about being wildly inappropriately controlling in a twisted Edward Cullen sort of way rather than perviness.

But it doesn’t really matter, because either way it’s outrageously inappropriate. Your friend should be straightforward with her and say something like, “Jane, I appreciate the clothing, but I prefer to buy my own underwear, thanks.”

{ 430 comments… read them below }

  1. Lillie Lane*

    Oh. My. Gosh. This is why I love this blog. Whack-a-doo. In one respect, I can *kind of* understand why underwear is important (well-fitting bras and panties shape the female form better and don’t cause lines), but there is NO WAY a boss should get involved here unless you are a fashion model. Did this boss expect her employees to model the undergarments as well? Mind blown.

    1. The IT Manager*

      I second: his is why I love this blog. Whack-a-doo.

      Other stuff is true too, but my mind did not go there. My mind went: “another top 10 cra-cra question.”

      1. Elizabeth West*

        Mine too. I was just about to click away and get back to work after finishing my tea, but then saw the link and was like, “WHOA!”

        WHO DOES THIS?????

    2. Diet Coke Addict*

      I can understand the concept of well-fitting undergarments shaping the line of clothing better–they do, it’s true. But the line between “enjoying ownership of well-fitting, well-constructed undergarments for your own self” and “forcing employees to buy said undergarments with your approval” is so enormous and bright that it’s next to impossible to figure out how this person crossed it. As long as the person is dressed neatly and office-appropriately, why does it matter if the woman in question is wearing Hanes from Walmart or Le Mystere or Agent Provacateur? Nothing about this makes sense! Unless the boss in question is requiring her employees to model, in which case it seems like this question would have been substantially different!

      1. Lillie Lane*

        This kind of reminds me when I was a teenager and my mom bought me a bra — she made me show it to my dad because technically he paid for it (she was a SAHM). Both he and I were pretty mortified, so I shoved it back in the bag and high-tailed it out of the living room. So happy she only forced me to do that once. I don’t know why telling him didn’t suffice.

        1. Kelly L.*

          My guess was she was worried he’d think she bought one for herself, and criticize the spending–so she wanted to make it clear it was for you. But so awkward!

          1. Toothless*

            My mom used to have me show purchases to my dad (not lingerie, thank goodness) — I think her thinking was that shopping was a bonding experience, and if he didn’t get to participate, he and I should bond over me showing him my new backpack and my North Face giant down coat.

            So, benignly wrongheaded but not completely bizarre.

            The original letter, OTOH, is completely bizarre.

            1. Jeanne*

              It is totally different to show new clothes to your parents when you’re a kid and this manager idiot. My mom always had us show my dad new shoes or clothes so that he felt part of what went on that day. He wanted to feel involved in our lives.

              This manager is a nut case. But maybe you all have a clue how they got to this point. Maybe the manager sees herself as a parent. She is in charge of teaching them to be proper adults. She is very wrong but it could be what is going on in her head.

        2. SerfinUSA*

          Off-topic, but I abhor the assumption that being a SAHM means the breadwinner has financial one-ups. The SAH part should be a mutual agreement, with 24/7 unceasing toil more than equal to the other person’s cash contribution. Imagine if dad had to pay for mom’s time and labor :/

          1. Koko*

            Right? At the going rate for a live-in nanny who also cleans and cooks, SAHM is “earning” somewhere between $20,000 and $40,000 a year depending on where they live. I would think that covers the purchase of a few bras.

      2. Teri L*

        Well, and regardless on her reasoning behind getting the undergarments, even if it’s for shaping the line of clothing, what is she going to do…force her employee to wear the underwear? What happens if the OP’s friend picks out random underwear, the boss purchases it and the OP’s friend returns it the next day/donates it to Goodwill?

      3. Vancouver Reader*

        Although if a boss wanted to buy me $500 bras that I wouldn’t be able to afford, I’d say go for it! (tongue firmly planted in cheek).

    3. AMG*

      This is awesome–in a horrifying way. Just when Alison (and the rest of us) probably thought we had seen everything!

  2. Dan*

    “If she were a man, this would be obvious perviness. I’m not sure if she gets a pass on that simply for being a woman”

    In the day and age of gender equality, the woman should most certainly not get a pass on something a man would get hauled into HR for.

    1. Windchime*

      Exactly. Man or woman, it would creep me the hell out if my boss wanted to look at my underwear under *any* circumstances. Super creepy and inappropriate.

      I don’t think I would even feel comfortable with the other parts of the shopping excursion. It just feels so invasive or boundary-crossing or something.

      1. Chinook*

        “I don’t think I would even feel comfortable with the other parts of the shopping excursion. It just feels so invasive or boundary-crossing or something.”

        I agree that it is boundary crossing by miles, but there are times when it is also necessary. I will forever love and respect my manager in Japan who took me shopping when I was working there and had my last growth spurt which meant some of my blouses and dresses no longer closed comfortably at chest level (who knew that this could happen in your early 20’s!).

        Due to my larger than the average Japanese woman frame and this being pre-internet, I had literally no idea where to buy professional clothing for me that would fit. She took me the local department store and was able to show me where the “oki sizu” department was and able to communicate my needs to the sales associate. Awkward – 100 times yes. Necessary – absolutely. Odds of it happennign to yoru average worker – 1 million to 1.

        1. Domi*

          +1 – I’ve had bosses/colleagues take me shopping too and was eternally grateful, but only when I was working in a completely foreign culture and wouldn’t have a clue how to go about shopping for myself, and even then I paid and no one approved the items but me! (okay, there was one case where the boss mentioned that there was another part to the outfit that wasn’t really optional if I was going to wear it respectably…)

          1. Chinook*

            “okay, there was one case where the boss mentioned that there was another part to the outfit that wasn’t really optional if I was going to wear it respectably…)”

            Been there, done that and totally appreciated the tidbit of knowledge as it usually isn’t something that is mentioned in any cultural awareness book. This is also why I appreciated the one coworker who took me to the public baths the first time (so she can teach me the correct nudity protocols) and is also why I have spoken up about how to wear/not wear coats inside a building to known new immigrants. Normally, I would never tell anyone to take off their mitts and jacket in order to warm up but if you are newly arrived from Africa in February, I am going to assume that you didn’t have parents telling you these tidbits when you are a child.

            But this is so much more about cultural awareness and not about controlling what is done with this information.

            1. Koko*

              Shoot, I have friends from Texas and southern California who had to be taught to take off their coat inside a building when they moved to a place that actually has winter.

              1. Rana*

                That’s because those places don’t heat their buildings as well during winter, and everyone’s wearing layers. It wasn’t until I moved to Minnesota, with its temperature extremes between freezing outside and over-heated inside, that I learned how to wear one heavy coat over much lighter indoor clothing. Before that, I’d be wearing multiple layers and only expected to take off one light layer when I came indoors, maybe two at most.

      2. Prickly Pear*

        I mentioned in an open thread that my only clothing goal is not to look homeless. When I have to step it up, I call my fashion squad- one member I worked with forever and she is teaching me the ways of professional dress (I come from the land of ‘as long as it’s not jeans’ work environments).
        I told my coworkers about this letter. I got the most horrified looks. It made my crappy afternoon just a little better, to think that at least my boss has no interest whatsoever in my undies!

      1. Kai*

        I don’t think Allison meant a pass in the sense that the issue should just be forgotten. Just that it’s possible for something other than general perviness to be at play in the manager’s bizarre need to approve undergarments for her staff. But regardless of gender, it’s gross and weird.

      2. manybellsdown*

        I read it more as “that’s WHY she currently seems to be getting a pass”, not that it should give her a pass. If it was a guy doing this to women, alarm bells would be ringing. Because it’s another woman, it’s been more confusing than alarming.

    2. Ask a Manager* Post author

      Just to be clear, I didn’t mean “I’m not sure if she gets a pass on doing this,” only on whether it’s reasonable to consider explanations other than perviness. Either way, she doesn’t get a pass on the situation itself.

      1. Anna*

        I think we’re also missing that she could certainly be interested in women. We can’t assume she’s straight unless anyone said so, so who knows if it is or isn’t pervy. This is not to say it in the vein of “All nonstraight women are hitting on any woman they meet” either, she could be bi or gay and still have another reason, like being controlling, but I don’t think we should assume everyone is straight.

        Just saying this as someone who isn’t straight and knows women are also capable of sexual harassment. No matter what her motivation though, I agree with Allison, it’s just plain wrong.

          1. Aunt Vixen*

            I’ve looked and looked for that and can’t find it in the threads. Was the comment deleted, maybe?

            In any case, if the boss lady is married to the boss man, big deal – doesn’t mean she can’t be attracted to women (and behaving inappropriately no matter whom she’s attracted to, let me be clear I agree).

        1. Observer*

          I don’t even think it makes a difference what her orientation is. Peeping Toms in all their variations come in all orientations and “interests”.

        2. Cari*

          So glad you posted this Anna, because when reading the letter I instantly thought maybe the boss is the kind of woman who plays a certain type of role in her *private* life (totally fine and not skeevy), and was now crossing a big Nope! line by bringing it into her work life and involving non-consenting adults in her play(?). I mean there are definitely a small number folks out there who get their kicks involving unwilling/non-consenting or just naïve participants in their sex-life (think flashers and the like), and like you say women *are* capable of sexual harassment (the stories I’ve heard in work about some of the older, straight women and how they treat younger men D:), *and* AAM does get some pretty bizzare and outlandish situations in some questions… IDK! Didn’t stop me wondering if there was something wrong in my head for going there though :S

          nb. I haven’t got through all the comments yet.

      2. Observer*

        It’s no more, and no less, reasonable to consider perviness in either case. It’s theoretically possible for a guy to do this for reasons other than perviness, and it’s theoretically possible for a woman to do it for reasons other than perviness. Realistically speaking, though, this is a case of “think horses, not zebras.”

    3. Sarah*

      I don’t think she should get a free pass on the boundary-crossing weirdness, but here it doesn’t seem like she’s doing it for her sexual gratification. It seems like it’s part of a weird desire to control her employees’ wardrobes and/or force them to “treat themselves” in a manner she approves of. I don’t think that it would be productive to treat it like a sexual harassment case just because if she was a man, that would be the assumption.

      That said, if a male manager was doing this to male employees only, sexual harassment probably wouldn’t be the first assumption for his motivations, but if a female manager was doing it to her male employees only, it probably would be, so it’s not a complete double standard.

    4. Melissa*

      Not to mention that some women are attracted to women! Her gender doesn’t mean that it’s not potentially pervy.

  3. CollegeAdmin*

    Sounds like your friend’s boss is Regina George.

    “On Wednesdays, we wear pink. No, not that pink shirt – the other one that I approved for you last week.”

      1. LBK*

        And The Plastics had no problem with Cady wearing Damien’s oversized polo as long as it was pink!

    1. Traveler*

      Haha. To be fair I’ve known quite a lot of doctors and dentists office that do this though. It makes them look more uniform without actually having a uniform.

    2. Cari*

      Is there a limit to the number of Mean Girls references that can be made in this comment thread?

    1. Biff*

      Yeah, I thought we were doing a weird wednesday feature or something. Mad Monday is good too.

    2. Kay*

      I know we can’t have WTF Wednesdays, but posts like this always make me pine for them.

  4. Katie the Fed*


    I, um…yeah I got nothing.

    The other issue the crazypants boss might not realize is that some religions specify undergarments to wear (I’m thinking of Mormons specifically) so she’s in potential dangerous territory on that.

    Also it’s just crazy, controlling, and rather icky.

      1. Emily, admin extraordinaire*

        We Mormons still wear bras, so she could still ask for approval on those (not that she should!). Under no circumstances is she allowed to comment on my temple garments, however.

  5. Kerry (Like The County In Ireland)*

    Is your friend working in a house of prostitution? Because that’s the only time “the boss” should have a say in her choice of underwear.

        1. Anonsie*

          And hilariously unsexy. I read through it once and all I could think is that I couldn’t imagine trying to act flirtatious and cute while wearing pantyhose tucked into gigantic outdated white sneakers.

          1. Koko*

            The dress code actually makes perfect sense when you consider that it’s oriented towards “look, but don’t touch.” Pantyhose with Daisy Dukes and sneakers is ridiculous, and would be absurd to the romantic partner who wants to touch your legs or take off your clothes, but from a few feet of distance, they even out the “skin tone” of your legs, smooth out the appearance of cellulite or wrinkles, cover up any budding stubble, etc. If you’re only looking and not touching, it just makes your waitress looks like her legs are not only perfect, but identically perfect to her fellow waitresses’ perfect legs. (Corporations, they love identical perfection.)

            1. Anonsie*

              Oh I get the reason they would want their waitresses to wear pantyhose. What I don’t get is why they have to wear hideous white sneakers with scrunched socks so they still look casual and sporty but then also have very heavy stage/dance hose. They’re like skin colored leggings.

  6. Crow T. Robot*

    This is so weirdly controlling. This woman literally wants to have a say in what is covering her employees’ butts. That is so far over the line.

  7. Betsy*

    I… feel like this is someone I worked for once. The same weird lack of personal boundaries. Although in her case, it was not buying us underwear, but shopping for hers at lunch and then wanting girl gossip type about them.

    1. MJ*

      I used to work for a small company owned by a husband and wife, and the wife always bought super-personal gifts for each employee at Christmas. One year, she gave me a nightie. It wasn’t lacy lingerie or overtly sexy or anything, just a very pretty cotton nightgown, but something about the idea of wearing something IN BED that had been purchased by my boss was just… off-putting. I gave it away immediately.

      I don’t think I could stay in a job where my boss thought she should know anything about my underclothes.

  8. BRR*

    Does anybody else think this is sexual harassment regardless of gender? I would feel very violated if my boss of the same (saying same because that is considered less egregious) gender got involved in any way, shape, or form about my underwear. It feels even worse because there’s follow up.

    If this was a subtle way of saying they need to dress differently at work I actually think it’s very nice.

    1. aebhel*

      If this was a subtle way of saying they need to dress differently at work I actually think it’s very nice.

      I disagree. I would vastly prefer that a boss simply tell me that my work attire is inappropriate than take me shopping (and treat me like a 12-year-old using Mom’s credit card) as a ‘treat’.

      1. PRWunderkid*

        Heck yeah. I hate shopping for clothes with anyone, even my friends, I could not do so with my manager. Especially the creeptasitc “approval” thing. If I’m wearing the wrong thing to work, tell me. Maybe suggest a couple of stores to shop from, but DO NOT TELL ME WHAT TO WEAR. (Unless it’s a uniform.)

        God, this is all so body-shaming, controlling and weird. I don’t even know what I’d do if my boss told me that we had to go clothes shopping together. Probably laugh in her face…

        1. Not So NewReader*

          I’d go even one further, I don’t like people telling me where to shop and how to spend my money.
          The fact that this is the boss’ money does not improve the creepy factor for me. It’s still pretty creepy.

        2. Melissa*

          Yeah, I also hate shopping for clothes with other people, so my manager taking me on a shopping trip sounds like a nightmare. Far less anxiety-provoking for you to just tell me my panty line is showing and that I need to handle that.

      2. BRR*

        I was thinking depending on the situation it could be nice because someone could be told their wardrobe is not appropriate but can’t afford to purchase new clothes. Weird. Crossing boundaries. But the heart being in the right place. It was more trying to figure out in this specific situation was might have been the reason for doing this.

        1. What the what?*

          I can see this. Assuming that in the OP’s friend’s bizzaro office they understand and accept the uncreepy-and-overbearing reason behind this and are ok with the shopping trips, an appropriate way for the boss to have handled this would be to tell them that they are also able to use up to $X on undergarments, then provide a gift card or charge up to that amount sight unseen to a company purchase order (the company DOES know about this, right?). As heavy female, the cost of bras can be prohibitive, so in a culture that accepts the concept of the boss buying clothes, this could be quite welcome and a good way to make a big impact on professional appearance. But demanding that they be purchased regardless of need and then asking to see them? Whole lotta nope.

      3. Loose Seal*

        I don’t see the shopping for clothes and having the boss pay any different than wearing a uniform that the company pays for. It’s not like the employees have to wear the clothes anywhere other than work, although unless they are very specific items for business or way outside the style of the employee’s regular wear, I would imagine they would.

        Underwear is over the line. Also, I can’t think of a business reason for wanting to supervise the purchase of the handbags unless the employees carry their handbags with them as part of the outfit for some reason.

        1. TL*

          The shopping is creepy. Guidelines and a budget would be okay (though weird); something like “You have $2000/yr for clothes; they need to be name brand, professional, and meet X style requirements.” would make more sense for a uniform.

          Taking me shopping is weird. So very, very weird.

        2. aebhel*

          Sure, if the boss was literally showing up with the clothing and telling the employee to wear it (although outside of a uniform situation, it’s still pretty weird). But making them go on a shopping trip? So not okay.

      4. dawbs*

        Doing it as a way of making them dress nicer is very much a ’17 pieces of flair’ way of doing things.

        If the dress code needs to be updated, it should be updated. If the dress code is such that people are violating the dress code in the boss’s head, but meeting the dress code that is on paper, it’s time to update the paper official dress code–not take a shopping trip to bring thigns up to the line in boss’s head

        1. Toothless*

          And if the boss can afford to dress on this level but feels the employees can’t, she needs to add a clothing allowance to their compensation package.

    2. BOMA*

      I’m with aebhel. If my attire needs to be more professional, I would rather have a frank conversation from my manager rather than her trying to take me shopping. I’m creeped out just thinking about going shopping with my manager.

      1. Apple22Over7*


        I have had a (very embarrassing) conversation regarding my underwear at work* and whilst it was embarrassing for all, a frank conversation was the only way it could have been handled. Certainly if my then-boss had taken me out shopping for knickers it would have been a lot more embarrassing.

        *Basically I’d lost some weight and as a result my work trousers were slipping down my backside, exposing my not-so-appropriate underwear unknown to me.

        1. AnotherAlison*

          IMO, the only thing inappropriate about underwear is the visibility. I cannot imagine someone telling you that you needed to choose granny panties vs. a thong (or whatever). When your pants don’t slide down, a thong is usually more discreet, no VPLs.

          1. HappyLurker*

            I have caught enough eye fulls of coworkers “whales tales” for a lifetime. This was the first thing that came into my mind…the boss was tired of looking at it.

            1. Windchime*

              Same here. Wear a thong, granny panties, or nothing at all. I just don’t want to see any of it. Knowing anything about my coworkers undies at all is too much knowledge for me.

          2. Elizabeth West*

            A boss asked a coworker of mine once what kind of underpants she wore. It had something to do with thongs, though the coworker wasn’t letting her undies hang out or anything. I think it was because she had no visible panty lines–we figured the boss had decided her underwear was inappropriate. No, boss, you asking about it was inappropriate!

            This wasn’t pervy–the woman was a control freak with nothing to do all day.

    3. Helka*

      If this was a subtle way of saying they need to dress differently at work I actually think it’s very nice.

      I dunno, it seems more passive-aggressive than subtle to me, if that’s the intent. A conversation starting with “hey, I need you to be better-dressed at work” and ending with “if that’s a financial burden for you, I’m willing to take you out and pick you up a few things to spruce up your wardrobe” might be appropriate, but as stated? It’s just weird, kind of paternalistic (maternalistic, I guess?) and when it comes to undergarments, really skeezy.

    4. Anon*

      Yes. The boss might not have any sexual intentions behind it. That might be a reason that she hasn’t realized just how inappropriate this is – she hasn’t considered that she *could* be sexually inappropriate.

      Doesn’t matter. I’d call it harassment.

      1. Elsajeni*

        Yeah, I would guess that that’s part of the issue — because they’re all women, she may be thinking of this as “Oh, just us girls, going shopping together and talking about clothes, what fun!” and overlooking the part where the workplace hierarchy makes it weird. (I mean, not that it wouldn’t be weird if they were peers, too — but if they were peers, the recipients of her “generosity” would presumably feel more free to say, “Jane, this is weird. I’m not going underwear shopping with you.”)

        1. manybellsdown*

          I can follow that train of thought right up until the point where Boss got upset that there was no underwear purchased. Ooookay can’t really reconcile that bit.

          1. Mallory Janis Ian*

            Yeah, the part about going to the lingerie department to check for any underwear on hold was really weird (I mean, even more weirdness on top of the initial weirdness). It seemed to me that the manager was all ready to get her jollies all riled up (The Office, anyone?) and that that plan was frustrated.

        2. Anonsie*

          This was my thought as well. She’s likely thinking “oh we’re all girls here” and not understanding how it’s crossing a lot of boundaries that she shouldn’t cross.

    5. Karowen*

      I wouldn’t call it nice, but I can definitely see how it may have started there and spiraled wildly out of control. If the manager doesn’t approve of how her employees dress but doesn’t want to write up a formal policy or obeys the “I know it when I see it” doctrine, that could make her reluctant to actually speak to the women, but willing to take them shopping to show them what good clothes are. It’s entirely possible that one of them wore a bra that was distressingly visible under the shirt and the manager responded to that by telling them to buy underwear that she had to approve. Obviously poor management skills, but may be nothing more than that.

      …For the sake of these women, I really hope it’s nothing more than that. I’d still get the hell out of dodge either way, though!!

  9. Chocolate Teapot*

    I think this post deserves a mention when we get to the end of year votes. (Either worst boss or just plain daftest post)

  10. Virginian*

    I don’t even have to read the post to know that is beyond all levels of grossness and inappropriateness.

  11. Ann O'Nemity*

    The employee said she didn’t want the underwear and she was still scolded. The boss’s behavior is so far beyond the pale that I can’t imagine she’s going to change, no matter what rational argument the employee presents. I guess the remaining options are to go to HR or the boss’s boss, or just start looking for a new job.

      1. Observer*

        Uh, OK. Am I the only one who is wondering if this is boss’ way of letting her husband “join the fun”? I’m just having a hard time getting my head around her husband not say “You know, I don’t think we can justify this as a business expense.”

        1. Stephanie*

          Especially for bras. They aren’t cheap! Doing this for multiple employees would add up, so I’m guessing the husband has to know something.

          1. HappyLurker*

            Seems like it’s wife’s way of “cleaning” up the office attire…making everyone look professional. It is still strange…

            1. Simonthegrey*

              Or making sure the females in the office aren’t wearing clothes that she thinks could distract her husband. It wouldn’t be the first time a married person has tried to police what other people/women wear around her spouse.

              1. Mallory Janis Ian*

                Ooooh — like, underwear to tart down the office, not tart it up.

                Wife to husband: OP is wearing granny panties everyday and I have the receipts to prove it!

    1. Not So NewReader*

      I think next time she should just refuse to go shopping.
      She could say that she is uncertain about the income tax implications.
      Or she could hit closer to the truth by saying “I am not comfortable with my boss paying for my personal items and pawing through my choices.”

      I have heard it said and believe it to be true: when ever someone gives you money there are always strings attached. So as long as all of you keep accepting the money her list of rules is probably just going to keep expanding. This is what money does to some people.

  12. alma*

    This is bananas! I would balk at any kind of clothes shopping trip where my boss bought me things, to be honest. But bras and underwear are in a whole new stratsophere of inappropriate.

    1. Loose Seal*

      My boss bought me a blouse once. But it was really related to office wear as we were supposed to bring in a white shirt to have printed with the office logo and I kept “forgetting” mine because I didn’t want a shirt with the logo. So my boss got fed up with me waiting and took me to a clothing store and said, “Pick out a white shirt.” She paid for it.

      Shortly thereafter, before the shirts were taken to have the logos put on, the shirt embroidery company went out of business. So no one ended up with a logo shirt. And I still have that white blouse.

  13. Elizabeth West*

    Yeah, okay, weirdo boss, if you want people to dress a certain way at work, then write up a dress code.

    There is no way in hell I would let my boss buy my clothes like this. I can’t even stand it when people in my family buy me clothes or accessories (they always get it wrong, anyway). I guess some of these people are thinking, “Hey, free clothes,” but NO. So totally inappropriate on every level.

    1. AnotherAlison*

      ” I can’t even stand it when people in my family buy me clothes or accessories (they always get it wrong, anyway).”

      In the past couple years, my mom has bought me a candy pink tanktop that is bedazzled in the chest area, and a candy pink t-shirt with a huge “have a nice day” smiley face on it. With the tank top, she told me she was just trying to buy me something I wouldn’t buy myself. Ummm, I wouldn’t buy this for myself because I am not 12, or a girly girl. How about buying me a Coach bag? I wouldn’t buy that for myself either, lol.

      1. Elizabeth West*

        My family DID buy me a Coach bag for Christmas! Though it’s too small for daily use, they actually got it right that time. It’s nice to know I have a decent bag. (Although now they will never stop, arggh.)

        1. the gold digger*

          My sister and my then boyfriend, now husband, bid against each other on eBay for a purse I really wanted. My sister was ticked that my husband drove the price up $30 and they were both ticked at me for telling both of them I wanted it. I had not expected that either of them would spend that much money ($200) on me for Christmas.

        2. smilingswan*

          What’s the problem there? The more Coach bags, the better, as far as I’m concerned. You can send any extras to me. ;)

    2. Alma*

      If the method in this madness is to encourage (or mandate…) a more professional mode of dress, the employer could arrange for a personal shopper in the local department store to spend a day helping the employee put together a wardrobe of work-appropriate clothing, including the foundation garments necessary to pull together the look.

      We have had discussions here about bras, camisoles, sheer undergarments, and visible straps on lingerie. A personal shopper would be able to guide in the selection of undergarments that fit the size and style of the employee, while making recommendations as to why the undergarment is a better choice.

      The employer should remove herself from the picture, yet authorize the personal shopper to charge purchases to his/her account.

    1. Ask a Manager* Post author

      But Christian Grey was based on Edward Cullen! It was originally Twilight fanfic. Also, Edward Cullen was crazy controlling (although not, as I understand, to the lengths of Christian Grey).

      1. Lo*

        Reason #7,023,432 why AAM is great: she takes the time to explain the origins of Shades of Grey (for what it’s worth, just a few days ago I had to do the same at my office…even explained what fanfiction is).

        1. Algae*

          Just to nitpick – *50 Shades of Grey* is repackaged Twilight fanfiction. *Shades of Gray* is a fantastic, surreal, dystopian novel that explores class and authority.

          1. Liz in a Library*

            Yes, please. Let’s not drag poor Jasper afforded into this. ;)

            Although the control issues of the caste system in that book are also interesting…

              1. Annie*

                I have “Lost in a Good Book” sitting next to me… its next on my list after I finish procrastinating over 2 cover letters.

      2. Felicia*

        I love that you know that!

        Edward Cullen and Christian Grey are the same person, essentially, though I too understand that Christian Grey is worse. The relationship between Edward and Bella hits all the red flags of an abusive relationship (breaking into her home and watching her while she sleeps, trying to control where she goes, what she does and who she’s friends with, cutting off contact with people he doesn’t approve of, among several other things).

    2. BOMA*

      Edward Cullen was super controlling in the Twilight novels (see: disabling his girlfriend’s car so she couldn’t visit her friend).

        1. Adam*

          I generally try not to judge people by the things they take in as entertainment as long as they’re honest about what it really is, because we all have some guilty pleasures. So long as we recognize the issues I figure it’s ok.

          Well I was once a roommate with a woman, early 30’s, generally left leaning, who was very vocal about women’s rights and such. She talked about the subject openly and posted a lot of politically active things on Facebook. She also LOVED the Twilight books and movies with a passion. I never really talked to her about the underlying issues with them for the reasons I listed above. I figure she knew about the problems already and just compartmentalized them like most of us do sometimes.

          But one day a bunch of us were sitting around talking about our favorite books and I mentioned that one of my favorite series was the Chronicles of Narnia. I had barely gotten that sentence out before she blurted passionately “Oh my God! Those books are so horrible to women!” My jaw hit the floor.

          1. Adam*

            *For the record: I fully recognize that the Narnia books can portray women and girls in problematic fashions based on outdated ideas and traditions. But if anyone were to try to argue with me that they were on the same level as Twilight or even worse in terms of unfortunate portrayals of females I would only be able to shake my head sadly and walk out of the room.

            1. Ellie H*

              I think compartmentalizing and how seriously you take various types of media is a reasonable explanation for this. For example I am somewhat bothered by the portrayal of women in Twilight but “Friend of Mine” (the song by Notorious B.I.G.) is one of my favorites to sing along to when I am completely alone. There are just different registers we take entertainment media in and I think people have categorizations of what they take seriously enough to find harmful and what they think is so silly it’s not really worth getting worked up about.

              1. Adam*

                I certainly wouldn’t call my friend a hypocrite or anything over this matter (and you obviously recognize that there can be issues in your own media choices), but the lack of consistency does put a wrinkle in things. When her Facebook recently became very outspoken against Hobby Lobby as a result of that court decision it does further become kind of difficult to take her opinion on any books all that seriously.

              2. Stephanie*

                I agree. As a hip-hop fan, I have to compartmentalize.

                What is worrisome is that some (probably younger) fans might not understand why some of this stuff is problematic. I cringe at teenagers thinking Bella and Edward have a normal relationship

                1. Anonsie*

                  That’s the thing that gets me– that behavior and relationship dynamic is considered totally acceptable to a lot of people, and considering the target demographic of the books, it just feels like an all around very bad idea.

                2. Stephanie*


                  I saw the third (?) movie as part of a MST 3000-type comedy show (i.e., the comedians mocked the movie in real-time while it showed on a screen).

                  After the wedding, Bella and Edward consummate their marriage in what was implied to be in a violent manner (the bed was broken). And then she gets pregnant. Aside from laughing at the jokes, I’m also thinking “Awesome! Yes, let’s tell teens that losing their virginity will be violent and immediately lead to pregnancy. That will give them completely healthy and normal views.”

                3. Anonsie*

                  Right? Not to mention how much of the “it’s not love or passion if it’s not aggressive” trope is strewn in the series as a whole.

              3. Kelly O*

                I can deal with misogyny in period literature, or in fantasy genres set in periods similar to historical periods wherein that was the norm. (Read: A Song of Ice and Fire) however Twilight bugs the bejeezus out of me.

                1. Anonsie*

                  I’m actually getting pretty tired of how every period-style fantasy series has to be rife with misogyny because it’s supposedly a replication of human history, even when the world it’s set in is completely fictional. It’s not really historical accuracy at that point, it’s your world, and world building is one of the most crucial parts of any series… Why doesn’t anyone seem to want to build a world where that’s *not* the way things are?

                  The counterpoint is that a lot of these are still the experiences of women in the present and it’s worth sharing, but it’s rarely shared well so I’m really feeling It’s Been Done Already.

                2. Ellie H*

                  @Anonsie – Do you like or have you ever read Tamora Pierce’s fantasy series? They’re YA books, but they are different in that respect. I loved them when I was a kid and I still reread them all the time and love them.

                3. Melissa*

                  @Anonsie – Also, a lot of writers display the historical accuracy 1) without romanticizing it AND 2) showing resistance to it. I just finished Kindred, by Octavia Butler, which is about a black woman who involuntarily travels back in time to the 1820s and 1830s. Yes, they show the terrible racism and sexism of the period – but it isn’t romanticized or shown neutrally; it’s explicitly shown as a terrible thing. Also, Butler also shows how the characters resist their oppression in ways both large and small. Sue Monk Kidd does the same thing in “The Invention of Wings.”

                  I feel like so many authors hide behind historical accuracy when they write, but it’s actually less accurate to portray all of your minority characters/women as if they just passively went along with everything.

    3. Biff*

      Edward was super duper creepy controlling in Twilight. He watched her at a night, disabled her car and prevented her from talking to people. Classic abuse situation.

      1. Chewbecca*

        My sister in law genuinely thought those things were romantic. I think someone I barely know sneaking in to my room to watch me sleep is so creepy there isn’t even a word to describe how creepy it is.

        To each her own, I guess.

      2. Whippers*

        Yeah, but I think Christian Grey did actually pick out clothes and underwear for whatshername to wear. So in a literal sense, this scenario is more Christian Grey than Edward Cullen.

  14. Who are you?*

    I have no words. I’ve tried, but I cannot find words to describe how horrifying this is to me.

  15. Donna P*

    I can’t wait for my friend to see the responses this is getting. She has always felt so obligated to shop with her. And in the beginning it was fun for her. She was able to get some great, stylish clothes and handbags — for free! But when she said something to me about bras and underwear, I just cringed. I’ll have my friend read thru all of this and I think she’ll really love the support and have the confidence to say what she really feels next time!

    1. Ask a Manager* Post author

      If you can convince your friend to come over here and give us more details, we would be VERY INTERESTED in any further context she can provide!

    2. Katie the Fed*

      What industry is this? MAYBE if they were club promoters or something I could understand. But no, not even then. I mean, if you care that much, then have a uniform.

    3. Lily in NYC*

      Can you please tell us what kind of business it is? I don’t need specifics but I would like to know if it’s a traditional office, retail, nightclub, etc.

    4. Sarahnova*

      The escalation on this has a nasty, controlling vibe to me. I can see where it’s hard, initially, to turn down an apparently nice bosslady saying “let me treat you to something”, but it’s slowly got more invasive where now we’re in the business of approving underwear. I don’t know whether this is sexually motivated (maybe she’s got a kink going with her husband, the boss) or she just gets off on the power, but it’s way way over the line and feels really… off.

      1. Jess*

        I agree…I get the feeling this isn’t just a gift and that the boss now has the employees feeling they owe her something…I shudder to think what. Very messed up situation.

    5. Jeanne*

      I want to know if there are any male employees and how they are treated. Do they go shopping? Do they buy underwear?

  16. mweis77*

    Even those crazy handbooks for cheerleaders in the NBA and NFL aren’t quite that bad. Ok, they are. But still. I did hear on a This America Life episode a former Laker girl was instructed on which push-up bra she had to by from Frederik’s of Hollywood. I’m assuming the letter writer is not a professional cheerleader.

    1. Melissa*

      A push-up bra from Frederick’s…as opposed to a sports bra? When you are out on the field bouncing and dancing around? Yeesh.

  17. Poohbear McGriddles*

    Yeah, if my boss wanted to approve my boxers – or worse, mandate that I get something else – that would certainly make my spider senses tingle. Whether it’s perverted or just very poor boundaries, it’s certainly inappropriate and not something anyone should have to put up with.
    If the boss wants to buy everyone matching polo shirts, fine, but I can select my own banana hammock, thank you.

    1. Biff*

      I believe if I was in this situation, my only option would be to choose the most gawdawful, horrifying choices I could manage to dredge up. Spongebob boxers? DON’T MIND IF I DO. Plaid shirts, dotted ties? REALLY SPIFF. That awkward shade of mushroom khaki. HECK YEAH.

  18. TheExchequer*


    Under no circumstances would I go clothes shopping with someone from work. (As a larger woman, clothes shopping is fraught with enough issues doing it on my own).

    Underwear approval?!? RESUME UPDATE TIME. (Though I can only imagine how you would try explaining it to the next job!)

    1. Laura2*

      Honestly, I’d probably just explain very briefly what happened. “My manager insisted on buying me lingerie and approving my selections, and I’m not comfortable with that.”

      1. Anon Accountant*

        That’d be very interesting conversation. “Why aren’t you at your last job”? Well, my boss insisted on buying us bras and underwear but she had to approve them first…..

      2. TheExchequer*

        I honestly cannot see myself saying that with a straight face to an interviewer, especially if they were male. I would rather sink into the floor and die.

    2. OriginalYup*

      You know?! I’d be tempted to submit my letter of resignation with a photocopy of my @ss wearing the unapproved underpants.

  19. Nodumbunny*

    *Jimmy Fallon Thank You Note music* Thank you, wacky control-freak boss who has nothing better to do than think about her employees’ underwear, for lending new meaning to the phrase “getting your (employees’) undies in a bunch.”

  20. Adam*

    You…you just can’t make stuff like this up. As a guy, I never in my most bizarre substance influenced dreams would have imagined my manager (also a male like me) taking me shopping, much less directing me to what sort of undergarments to buy.

      1. Adam*

        Agreed. Thank goodness in this case the OP’s friend and her manager’s genders match. If there were any sort mismatch the warnings would go from red to full on purple alert.

        1. Sarahnova*

          Given that the big boss is this woman’s husband, I have the horrible sneaking feeling that this is a sexual deal between the two of them, where one or both of them gets off on knowing they control their employees right down to the underwear.

          …but I really hope I’m wrong. :(

          1. Loose Seal*

            I could be that an employee mentioned needing underwear to the boss and she agreed to pay for it. Then, perhaps thinking that it might look like favoritism if they bought underwear for one employee and not the others, included it in this year’s edict.

            So it might not be a sexual thing at all. It might just have been kindness that wasn’t run all the way through the weirdness filter.

            1. Loose Seal*

              It could be*

              Ordinarily, I don’t correct typos but I was afraid the “I” at the beginning might lead people to think I was the employee in question.

            2. Sarahnova*

              I would like to believe your charitable interpretation, but I do have a hard time seeing where “berating the employee for not picking out any underwear for approval” would come in. Or why she was insisting on approving purchases in the first place.

              1. Loose Seal*

                I’m looking at this based on a boss I once had who agonized that she couldn’t pay me more yet we still had to dress nicely for the job. It didn’t bother me to wear the same five or six outfits over and over again so I never felt the need to go shopping as long as my clothes were in good repair. But she would bring stuff in for me all the time and if it was something I couldn’t make use of (like a pair of shoes with way too high a heel for me) and I thanked her but refused it, she would get hurt that I didn’t accept. She never scolded me but I can see how some people could allow their hurt that one wouldn’t accept their generosity to come out as irritability.

                1. hildi*

                  Yeah, your situation is a lot more on the up-and-up and I could see being reasonable between two people that are ok with the arrangement. Nothing too crazy there. But this one here has that element on control (approving the purchases), which is probably what makes it even worse of a situation.

            3. Big Stupid*

              Who would ever casually mention to her boss that she needs new underwear, even if it would be said while already out shopping for other stuff?

              1. Windchime*

                Nobody. And if, in some bizarre alternate universe, I have an employee who mentions that they need underwear but can’t afford it, I will either give them a raise or a gift card to Target.

              2. Karowen*

                Trying to see all angles here – It’s entirely possible that the woman was at work and her bra strap snapped or the underwire broke (I’ve had both happen to me) and she was in such shock that she said something about it out loud.

  21. De Minimis*

    I did work someplace where they had to specify in the dress code about “no visible underwear, and especially no thongs…” so maybe that’s what this is about, but it’s still crazy.

    1. Elysian*

      Yeah, I worked somewhere where our uniform was a white button down shirt, and I had an awkward conversation with my manager about what bras are ok with my white uniform shirt – (white or nude. not pink or black!!) and I thought THAT was crossing the line. This is just… I don’t have words.

      1. Ann Furthermore*

        Oh my gosh, yes, that would be a horrifying conversation. I can see where it’s coming from though — if there’s a standard they want everyone to follow that includes not being able to see lingerie. But still…I would just want to die. But not before responding that a better way to deal with the issue would be to spring for better fabric, rather than making managers have horrible, uncomfortable conversations with their employees. It is possible to wear a black bra under a white top without it showing through, if the top is made of good, high quality fabric.

        1. Anx*

          White bras under white shirts show up very easily. Pink (pale pink) is more subtle for me (I have pale skin with pink tones) than white.

    2. MaryMary*

      I worked at an office whose handbook required that employees wear underwear at all times (apparently it had been a problem in the past). I was okay with it once they assured me there were no surpirse inspections, the handbook was a way to formalize the rule so no one could say they didn’t know they needed wear undies to work.

      1. HM in Atlanta*

        I worked somewhere where the policy didn’t say you had to wear underwear, it just said no one should be able to tell if you weren’t (sheer tops + no bra were the source of that gem).

    3. TL*

      No visible thongs or no wearing thongs? Not to overshare, but I would have a hard time complying with that second one. (But also, my bosses would never know.)

      1. KarenT*

        An important distinction. My company sent out an updated dress code a few weeks ago and it had a section of banned clothing items that included exercise wear, ripped clothing, shirts with offensive logos, and undershirts. An hour later HR sent out a statement clarifying that undershirts were in fact allowed, but must be worn under clothing but not as one’s only shirt. It was hilarious! I couldn’t stop laughing at the thought of those who had thought our HR department was banning undershirts under clothing.

      2. smilingswan*

        I don’t think they could ban all thongs, just visible ones. Because really, there is no way to prove someone is wearing a thong unless they show it to you. You could make an educated guess, of course, but you can’t discipline someone regarding what you think they are wearing.

        1. smilingswan*

          Well they could ban them, I guess, but I don’t see how they could enforce the ban.

        2. HR Diva*

          Oh you can tell – it’s one of those dress rules that just because you can, doesn’t mean you should. Butt cheeks swaying in the wind…
          and while we are on it – spanx are not for chubby chicks (we look like sausages) they are for skinny girls with wobbly bits.

    4. Anx*

      “no visible underwear”

      Do you think this generally refers to keep underwear hidden under clothes, or not outlines?

      Because if I’m wearing slacks and or a blouse, you can tell I have a bra and underwear on. I try to wear the sturdiest clothes I can find and wear modest underwear with clean, simple lines…but I can’t afford seamless things and there is no way I’m wearing a thong.

      1. Rayner*

        Generally speaking, no visible underwear refers to it being seen outside of clothing, like visible thongs over waist bands or coloured bras that show through white shirts. Nobody’s expecting you to wear layers and layers just to minimise a bra line.

        1. Anx*

          Oh good. I think use of “visible” in Visible Panty Line and in “no visible underwear” got me on edge for a minute. Thank goodness.

  22. Kerry*

    I love how this got crazier and crazier as I scrolled down. “Their boss takes them shopping, how nice! …For work clothes, that could be really thoughtful in the right circumstances!

    …and bras and underpants?

    …and the boss is going out of her way to physically look at the underwear?

    …and the LW was told off for not reserving any underwear for her boss to look at? WHAT WHAT WHAT WTF”

    1. Mints*

      I know, I read it in the same “meh…what!!” escalation. Where at first, it’s like, that’s a little weird, but I could see how a generous but misguided boss would do that. Then the end is like nopenopenope

    2. Cara*

      I think this is probably exactly how the progression worked in real life, too! The first month, the boss says, let’s go shopping for a new handbag, you deserve it. The employee’s thinking, well this is unexpected, but hey, new handbag!

      Second month: I feel like going shopping, how about we go pick out some new trousers? My treat.

      Third month: OK, let’s find the shoe department… Oh look, the lingerie department’s having a sale. If there’s anything you need from here we can just add it to our order.

      And so on to kind of slowly establish this precedent of the boss buying the workers’ clothing, getting incrementally weirder and weirder so that by the time the boss is chiding the employee for not picking out any underwear for her to approve, it just looks like a progression of the arrangement they established months ago.

      1. Not So NewReader*

        It felt like grooming for something to me… but that could be my own paranoid thought.

        1. Vancouver Reader*

          For when the alien is tired of the current host and needs a new one to take over.

        2. Sarahnova*

          No, it feels that way to me too. I have a sensitive radar thanks to past bad experiences, but honestly, it hasn’t yet led me wrong as to when something is hinky and some bad power dynamics are going on.

  23. Nina*

    This would creep me out so much. This isn’t just crossing a line, this is taking a giant leap over it. Truly bizarre.

  24. Rebecca*

    To me, this is so far out of line I can’t even comprehend it. Unless your underwear are showing because you’re doing a television show, and the wardrobe department specifies what you must wear, NO NO NO NO NO!!

    This is just plain weird.

  25. Sunshine*

    Does she have male employees? And do they get the same “treat”?

    Holy Mother. I cannot imagine anything more uncomfortable.

  26. Sunflower*

    This boss is nuts! What does the other coworker think of this??

    And where are the funds for the clothing coming from? If the money is coming from HR to be used for morale boosting events(like lunches/gift cards) I’m not sure how they would feel knowing the money was used to purchase clothes and in this way.

    1. Nina*

      I’d be curious to know what HR thinks as well, especially if these are high quality, expensive pieces that she’s buying.

      If the boss is paying for it herself, maybe she’s doing it as a tax write-off? I have no idea. The whole thing is so strange.

      1. Thomas W*

        I find donations to be a better tax write off than underwear for people who aren’t me, haha. Sure you’d agree!

  27. Nm anon*

    I had a boss that did aomething similar. We moved to a new location and she decided it was time for a dress code change to business causal, no jeans, tshirts, or sneakers where they were previously allowed. We were already underpaid and complained. We had to complete tasks or take tests and were given X amount of dollars to go buy new clothing, which we had to bring in, show everyone and allow her to approve and provide her with the original receipt. At least she didn’t flip when I didn’t buy new undies!

    1. GrumpyBoss*

      Ugh… at first when I started reading this, I was thinking, “OK, that’s not so bad… a boss who is aware of the financial impact of a policy change”. Then I got to the show-n-tell portion.

      Just ugh.

      1. Nm anon*

        It was just another form of control. She is truly a horrible person. Worst person i have ever met.

  28. Allie*

    I’d love her to try and buy me a bra in a dept store. 32G, baby. Maybe of you’re crazy and want to stay, you could say you have an odd bra size and request cash. Might as well bill her for clothes for your future interviews.

    1. Zahra*

      Oh yeah… or I’d totally take her up on her offer… at my favorite mom and pop lingerie boutique. 100$+ per bra sounds fine, right? They’re good quality and will last years!

      1. Stephanie*

        Yeah, exactly. In the same boat. I’d find the laciest, frilliest, fanciest one at a boutique and innocently be like “I know it’s $120, but you said I needed new bras, right?”

        1. Cara*

          So at what dollar value does this go from being incredibly creepy, controlling, potentially voyeuristic behavior to becoming a fun perk of the job?

          1. Stephanie*

            Ick…never. Like Allie said, I’d just take advantage of the creepiness while I looked for a new gig.

            “Hey boss, while we’re here at the specialty lingerie shop, how about we check out the suiting store as well?”

          2. Zahra*

            “What not to wear” budget territory for me… per employee per outing. But then, I never was in a similarly creepy situation and I don’t know what kind of vibe lady boss is giving off. But, in general, I’d rather find my own shopping buddy (and don’t need any when shopping for bras: I manage fine alone, even if 120$/bra is actually pretty average for 34J me).

    2. Melissa*

      Yah, this. The only bras at a department store (as opposed to going online to a specialty boutique) that will fit me are going to be upwards of $75, *at best*. Odd bra sizes FTW *sarcasm*

  29. Kai*

    This reminds me of Michael Scott taking the women in the office out for a day and offering to buy each of them one item from Victoria’s Secret.

    1. Ask a Manager* Post author

      When I turned 21, my then-boss (a man) gave me a pack of wine coolers and a gift certificate to Victoria’s Secret. At the time, I was young enough that while had a vague inkling it was a little icky and inappropriate, I didn’t pay all that much attention to it. But in retrospect now, WTF? I mean, what is the message there — “now you can drink legally and you will need a new bra to go with it”?

      1. Anonylicious*

        Oh, my goodness. Somehow the fact that it was wine coolers makes it even skeevier for reasons I can’t quite articulate.

        1. Mints*

          I think it’s because that’s like, a juvenile drink. Alchopops (sp?) are the most popular drink for minors because they don’t like the alcohol. A bottle of wine would still be weird, but it sends a different message

        2. Stephanie*

          Yeah, those are stereotypically what inexperienced drinkers drink because they’re super sweet and don’t taste much of alcohol. I definitely remember dorm parties freshman year with all the colors of the Boone’s Farm Rainbow. The combination of syrup and alcohol gets you drunk quickly (after multiple ones, that is) without the unpleasantness of shots of high-proof liquor. So giving those as a gift to a just-legal drinker (along with a Victoria’s Secret gift card) kind of screams “I am going to take advantage of your low alcohol tolerance.”

      2. Sarahnova*

        Maybe I’ve just had too many bad experiences, but the message I would receive is, “I will enjoy picturing you drunk and in undies I paid for, because I not-so-secretly want to sleep with you and am hoping you feel so grateful that you drink the coolers and then show me the undies”.

        ALL THE ICK.

      3. the_scientist*

        As a 21-year old co-op student, my (male) manager gave me a giant stuffed animal on my last day at work. The entire lab had come together to give me a really lovely gift (a glass serving tray that was clearly hand-made and hand-painted; it’s gorgeous and I use it all the time) so there was no reason for this extraneous gift and the stuffed animal part of it made the whole thing really strange.

        1. Traveler*

          Yeah my mind goes immediately to the winning your girlfriend a prize at the fair stereotype.

        2. en pointe*

          Ha, stuffed animal is weird.

          Last year when I was relatively new, some of my coworkers brought wine and a big cake with a giant ’18’ on it for my birthday. It was super sweet… except for the awkward moment when it was actually my 19th birthday.

      4. Traveler*

        Ugh. Strange gifts from male bosses is the worst. I hate playing the “Is this skeevy or is this just older guy not knowing what to do and trying to buy something he thinks a woman would like” game. Just a happy birthday or a congrats would be so much more appreciated. I also played that game with customers when I was front facing. My favorite was the guy who came back the next day and said “Sorry about that, my ex wife told me that was creepy and I shouldn’t have done it.” I wanted to hug her for it, and give him a thumbs up for his attempt at being decent, but then I also wanted to know why they were talking about me.

      5. Mimmy*

        Alison – If it makes you feel any better, I probably wouldn’t have thought much of it myself at that age either…I was incredibly naive back then.

      6. Sadsack*

        When I was 18 and a high school senior, I worked part-time for a local attorney. He and his wife had gone to London for vacation, and returned with gifts for his main secretary and me. The attorney came in and gave us our gift boxes. The secretary opened hers first, a nice large ceramic bowl of some sort. Mine was a short, gauzy robe from Victoria’s Secret. The secretary and I were looking back and forth between our two gifts while I tried to sputter out something to say, which basically was, “Uh, thanks?!? This is…pretty?”
        A couple of days later the boss’ wife came in, she asked if we liked our gifts, said she hoped so because she picked them out. I think she was trying to get me something a young person might like, and since this was about 25 years ago, I think VS was sort of new and she thought I might think it was cool. I was mortified though.

        1. Amy*

          Was it actually from VS? And meant as a gift from London? Because we didn’t get the first VS store here until 2005. Sorry if that adds to your creepiness…

  30. Loquaciousaych*

    My husband and I paid for a dear employee’s wedding dress as her wedding gift- but SHE picked it, not us.

    1. Chloe Silverado*

      I know some might view it differently, but I think that was very kind of you. Offering to pay for an expensive item as a gift for a life milestone is very different than taking your employees underwear shopping.

  31. Gene*

    If she were a man, this would be obvious perviness.

    This may just be the most sexist comment I’ve ever seen from Alison. Since I have a Y chromosome, I’m guilty? If something is pervy, it’s pervy; no matter which gender is responsible. And this sends the probably pervy flag to full hoist.

    1. Ask a Manager* Post author

      I actually don’t think it’s true. For instance, as a woman, I could offer to help someone I didn’t know very well, say, zip up the back of their dress and have it come across perfectly wholesomely — whereas it probably wouldn’t if I were a man.

      1. Case of the Mondays*

        Funny story. I had to have my assistant help me w/ a zipper once. My husband was traveling and I put on a sheath dress that I had just bought. It was too low cut in the front and a little too tight in the chest. I managed to get it zippered to try it on but for the life of me could not get it unzippered to take it off. I buttoned up blazer over it, grabbed a cami and went to work. I then asked my assistant to help me unzip it so I could get a cami under it for the day. It was hysterical even though it was embarrassing. I have an old shoulder injury so I have limited rotation in one direction and I think that’s why I was able to get it up but not down. Luckily my husband was returning that night and I stayed in the dress until he could completely free me from it.

        1. Case of the Mondays*

          To be clear, I bought it online so that is why I didn’t yet know it was too snug.

        2. the gold digger*

          I have a great vintage dress I got at consignment that I have to ask someone else at the Y to unzip every time I wear it. I knew that would be an issue when I bought it, but it was worth it.

          (Brown tweedy sheath with fake fur lining the neck and the sleeves. Total ’50s gorgeousness.)

      2. manybellsdown*

        Also have you ever been in the restroom and some lady says “do my undies show through this fabric?” or “do I have anything on my rear?” That’s a thing strange women often do for each other.

        Unless I knew the guy in question, big difference if a dude goes “hang on, there’s something on your tush.”

        1. Mints*

          Yeah, one time a strange woman asked me about my underwear, which sounds ridiculous but she didn’t creep me out at all. (I was wearing a cheap white dress, and she was like “I know this is really weird to ask, but I just bought the exact dress without trying it on, but it was see through once I put it at home. Can I ask what you’re wearing under?”)
          Yeah, context matters

      3. Gene*

        I would tell a woman that the back of her dress/skirt is not properly zipped – and have on more than one occasion. That does not make me a perv. Walking up to her and zipping it for her might.

        What got to me was the blanket statement. If you made a blanket statement here that all women are overly emotional in response to a question where a female boss was overly emotional at work, you would rightly be called out.

        1. Layla*

          Well, let me play devil’s advocate. Say the employee was male, had a male boss, and he asked employee to go out for drinks after work a few times. Then he invites you to a ball game. Most men won’t think anything of it. Now say the boss was female. The employee would be more likely to think she was trying to hit on him. I just took it that the employee would have been more on guard if it was a male boss as opposed to a female, who, whilst being unprofessional in doing this, might be just wanting to make some friends.

      4. Anx*


        This boss’s behavior has the potential to be sexual (gender) harassment or just plain creepy.

        But there are many things that a woman coworker can do for and with me than a man simply can’t without making me uncomfortable.

        I can use a locker room with coworkers of my gender, regardless of their orientation, without blinking an eye. I would not be be comfortable in a co-ed locker room.

        I wouldn’t be thrilled about a woman I worked with coming up to me and fiddling with my zipper to fix it, but it would be a worse violation if a man did that (at least a man with a masculine presentation). I mean, If I ask something to hook my top hook on a dress, and there’s a mixed group, I’d ask a woman first (or a man I felt closer to). And I’d ask a man to fix it if he was the only person there. But there are different levels of comfort I have with different genders doing gendered or intimate activities with.

      5. HistoryChick*

        I used to work at a historic site/museum and I often wore 18th century clothing (which included stays…18th century corsets). My stays were back lacing and I couldn’t get in or out of them myself. My husband usually laced me in, in the morning, but in the afternoon I usually asked a female co-worker to help. One time she wasn’t in the office and the rest of the employees were all male. I just suffered in my stays, drove over to a neighbor’s house after work, and had her get me out of the darn things. Moral of the story: make sure your stays are front lacing.

        1. hildi*

          On the surface that sounds like such a cool job. When you talk about stays and corsets and all that I always like to marvel at how lucky I am to live in a time where I can read a book (well, Kindle!) laying down on a couch in my sweats and tshirt and comfortable bra. But all these historical fiction books I read – the women were wearing their full complement of clothing sitting UPRIGHT (the horror) reading. It just really caputures my imagination – i would love to dress up and playact for a job, though.

    2. Katie the Fed*

      “Since I have a Y chromosome, I’m guilty”

      Were you wanting the right of approval over your female employees’ underwear? Then no.

      And yeah, can’t argue that doing this to the opposite gender kicks of the pervy concerns a lot more. A man doing this to female employees/women doing it to men – super pervy. Same gender – weird, inappropriate, maybe pervy?

    3. Biff*

      I don’t think that’s what was meant. I think it should have been understood that, if this was a man, people would have already put a stop to it, under the pretense of ‘too pervy’ regardless of the real reason. It’s the setup for her next point, which is that this boss seems to think she can’t be pervy because she’s female (which is untrue.)

    4. Chriama*

      I’m all for gender equality, but I think that’s a deliberate misinterpretation of her statement.

    5. alwaysbenicetotechsupport*

      Gene- that’s not what she’s saying… it’s that this seems to be more-acceptable (or at least in a grey-ish area) since the manager is a woman. if a man were doing this same thing, it’d obviously be pervy. but, since the manager’s a woman it’s harder to tell if she’s pervy as well as a controlling whack-a-doo.

    6. Sarahnova*

      Rightly or wrongly, men have a much-worse reputation and history for inappropriately sexualising their relationships with women. That said, Alison is quite clear that it’s inappropriate regardless of the genders and sexualities involved, and that the reason why this woman is doing it ultimately doesn’t matter.

      I have never had a female coworker or work contact sexualise their relationship with me. I have lost count of the number of times a man has done so. That said, I would object equally to a male or female boss wanting to approve my underwear, and I think this is creepy as all get out.

      1. Zillah*

        Yes, ditto. And, I think it’s fair to say that men deservedly have a much-worse reputation for it. That’s not to say that all men do it, but it’s a common behavior with a long history, and IMO, men who don’t keep that in mind when they’re interacting with women in ways that could be construed as sexual are pretty callous.

        What this boss is doing is inappropriate. That’s clear. And it may be super pervy. But I can also see other reasons behind it, though those reasons are also inappropriate.

    7. Whippers*

      Well generally men are sexually attracted to women and women are sexually attracted to men. That’s why something like this is generally pervy when directed at the opposite sex If the person in question is attracted to the same sex, then it also becomes pervy.

      1. Zillah*

        Totally disagree. There are plenty of things that women (and presumably men, but not being a man, I can’t speak to that for sure) can say to each other regardless of sexual orientation and have it come off much less pervy/creepy than if a man said it. That’s because regardless of sexual orientation, women often share body issues and concerns.

        For example: a man chiming in on a conversation about how difficult it can to find button-down shirts if you have a larger chest or how difficult it can be to find a bra with a small band but a DD+ cup is going to come off as super creepy in almost every situation. A lesbian? Not so much, if she has the same issue.

    8. The Cosmic Avenger*

      Dude, if you don’t get it, then you’re definitely that creepy, socially awkward guy that skeeves out all your female associates. Even giving you the benefit of the doubt and assuming you don’t mean it to be skeevy, if you treat them EXACTLY as other women treat them (as others have explained, so I will not go into examples here), it will be at best uncomfortable and awkward, and at worst it will trigger post-traumatic flashbacks or full blown anxiety attacks.

      However, if you exchange “pervy” or “skeevy” for “inappropriate”, you’re close, but only an oblivious, privileged person could not understand the huge difference between merely being inappropriate and abusing one’s position of power or privilege (even unintentionally).

      1. Ask a Manager* Post author

        In fairness to Gene, I could see how he could see this differently without being a creepy, socially awkward dude himself. (And strongly suspect that he is not, given his track record of smart, thoughtful, nuanced comments here.)

  32. Poohbear McGriddles*

    Hmmm, if the boss’s boss is her husband, could he be the one calling the shots regarding the clothing selection? Maybe she’s just doing his dirty work (pun intended).

    That’s not to say that women aren’t capable of cooking up crazy all by themselves.

    What if the employee prefers to go commando?

    1. CollegeAdmin*

      What if the employee prefers to go commando?

      I’ve been containing my laughter at some of the comments here, but I lost it at this one. +1!

      1. GrumpyBoss*

        That is exactly what my smart ass would have said if my boss asked me to go undie shopping.

  33. OliviaNOPE*

    This CAN’T be real. Although I once had an employee who absolutely refused to wear undergarments to work. HR had a talk with her about it a few times as gently as possible, but she still insisted on not wearing a bra to work. It would’ve been nice to gift her a bra :-/

      1. OliviaNOPE*

        Yeah they said there wasn’t really anything they could do. This was a government job if that makes any difference. Anyway, thankfully she wasn’t particularly well endowed so it wasn’t as bad a scene as it could have been I guess.

        1. De Minimis*

          It shouldn’t matter as far as it being government, although it does sound like they failed to have a clear enough policy which I guess permitted her to skate by. Still pretty hard to believe.

          The better policies tend to give management some leeway to say that something isn’t ok.

          1. Toothless*

            I have a small-chested friend who would probably be majorly inconvenienced by a dress code that said, “You must wear a bra,” but I’m pretty sure she would comply with one that said, “Two layers of fabric between your nipples and the customer at all times.”

            1. Loose Seal*

              If I saw a dress code that indicated I needed two layers of fabric over my nipples, I would raise Hell if the guys didn’t have to do the same with undershirts or wearing their suit jacket or vest all the time.

              I wear a bra but I’ll be damned if I let someone tell me I have to.

              1. Relosa*

                I used to work at a place that had a family dress code for the guests. We couldn’t say it outright but we called it the nipple policy. Men would get SO upset when we asked them to put a shirt on – “Women can walk around in bikini tops and that’s okay?!” (outdoors, hot, summertime)

                I always told them that nothing stopped them from wearing bikini tops…a few took my advice, haha.

                At one point the policy was amended to include ‘gender appropriate clothing’ but then changed following to ‘everyone must wear a shirt that is at least mid-riff’ which pleased bearded hipsters and belly-baring women alike…finally.

            2. Chriama*

              I’m not sure if you’re being tongue-in-cheek here, but that wording is a lawsuit waiting to happen (possbily frivilous, but still a pain for the company). If the dress code says professional and modest attire, I think a reasonable person would agree that visible nipples cross that line. Also, policies should be written with the end goal in mind. Does the employer have a right to dictate an employee’s choice of undergarment? Probably not. Does the employer have a right to dictate how the employee’s choice of clothing affects the work environmnent? Well usually yes.

      1. Arbynka*

        I thought of 30 rock.

        Liz: Okay, this is gonna sound really weird. But, um, you need to wear a bra.
        Cerie: Oh, no. I… I don’t actually. They kinda just stay up on their own.

        1. Cari*

          Gonna remember that comeback next time someone tells me I should be wearing a bra :D. Don’t see the need so long as my top is thick/dark enough.

    1. Adam V*

      > HR had a talk with her about it a few times as gently as possible

      I don’t see why HR didn’t follow up the “gentle” talks with a final conversation that went something like “your clothing doesn’t fit our dress code; we’ve told you this before, so this is your final warning; sign here to indicate that you understand that we’ve had this conversation”, followed by termination if she did it again.

    2. aebhel*

      I frequently don’t wear a bra to work, but I think you’d have a pretty hard time telling that, given my chest size and general taste in clothing.

      1. Whippers*

        I like to wear a bra just to keep the back fat in place. I don’t have a big bra size but don’t you feel really…wobbly?

        1. Relosa*

          One time I got a tattoo on my ribs and had to go about three weeks without a bra – I’d only occasionally wear a sports piece for workouts.

          It was during winter, so I ALWAYS wore a hoodie anyway, but with a tank top underneath my shirt it wasn’t as noticeable as I thought it would be on my own end.

        2. aebhel*

          Nah, not really. I’m pretty skinny and not particularly well-endowed in the chest area, though, so ymmv.

    3. HM in Atlanta*

      I mentioned this earlier – but one employer’s response was to say, “I don’t care if you do or don’t – I don’t want to be able to tell either way”

      1. Windchime*

        I believe my company’s dress code actually says something like “Undergarments or lack thereof should be undetectable.” So if you don’t really need a bra and nobody can tell you’re not wearing one, then no biggie. If I was to show up to work without a bra, it would definitely be detectable and uncomfortable for everyone.

      2. NoPantsFridays*

        Yes, this is how it should be. If I’m your coworker, your undergarments are none of my business; so don’t make them my business! :)

    4. Relosa*

      I dunno, I find it weirdly controlling to dictate that women MUST wear bras at work. What is the reason for it? Is unfettered, jiggling breast fat that offensive? Are men or anyone non gender conforming required to wear them if they have breast fat as well?

      I don’t disagree that it’s unpleasant, but as long as no one is running around naked and otherwise looks groomed, showered, and ready for the job, I am totally fine with their choice to not wear undergarments. It’s not my body, and I can choose not to look at theirs.

      1. Cari*

        With you on the weirdness. I always felt the way people are scandalised by women not wearing bras comes fom the same place as the objections to public breastfeeding :|

        1. Jen RO*

          Continuing from the post below: yes, I am against public breastfeeding if it means I can see your boob. No thank you! If you can do it without anything showing, I don’t care (and I probably won’t even know).

          1. Cari*

            I’m referring to the way some people feel aggrieved at even *discrete* public breastfeeding, and how obvious it is they believe breasts are for one thing only (and it ain’t food). It was meant to be a throwaway comment, assuming others here would have observed the same reactions, d’oh :)

          2. Zahra*

            Actually, having a big cover just highlights what you’re doing and many, many babies won’t stand for a cover over their heads. However, when done well, you only see the nipple for the time it takes to uncover it until it gets into baby’s mouth, so a few seconds. As for the rest, you see more in ads for lingerie stores and on the beach.

            1. Relosa*

              This. Next time you sit down to a hot dinner, but a towel over your head keep your face right next to the plate.

            2. manybellsdown*

              Oh yes, my child wouldn’t tolerate a cover at all. But really the baby covers pretty much everything. I mean, I’m sure there are some women somewhere who will fling their boobs around in Starbucks, but generally we just want to get it over with and no one will see anything unless they’re really staring.

      2. Rayner*

        As a person with huge boobs, I can assure you it does look very unprofessional and unfortunately, it doesn’t fit in with typical western attitudes towards business dress.

        However, men do have the luxury of not being required to wear a bra no matter how much jiggling boobery they have. Double standards, oi vey.

        1. Relosa*

          I dunno. I am also pretty large chest-wise and I just see more than double standards. Again, if it’s loose, unsupported fat that is so unacceptable, why do we not require those who are obese or with loose skin to wear girdles?

          When the standard is equally applied, it’s pretty easy to see that it’s just good old-fashioned body shaming. It’s entirely possible to look professional without a bra. That being said, I do choose to wear one, but like others said, I’ll be damned if someone judges me based on whether or not I do wear one – especially in the workplace. My boobs, hidden under clothing, mind, have nothing to do with my job. They’re mine and no one else’s territory. They’re not like body odor which can actually affect others, it’s not like hair which sheds, it’s not like communicable illness which makes others sick. They’re boobs. That’s it. They serve one evolutionary purpose…and professionalism isn’t it.

          (not railing on you, just bringing up a point as to how absolutely ridiculous it is, beyond just the double standard with men)

      3. Jen RO*

        I don’t want to see nipples through clothes. Anyone’s nipples. And I don’t think you can control whether or not yours start showing… (If you’re wearing layers and there’s no way to notice the nipples, even without a bra, then I don’t care.)

        1. Relosa*

          I’m just saying that you have the choice to look away. Of course no one can help when something first enters their field of vision, but after that, it’s up to you. Honestly I’d be annoyed if I were braless in the office and you were offended by my nipples so much you had to keep staring at them and thinking to yourself how offensive they are.

  34. Career Counselorette*

    True story: I did a very brief stint for a well-known specialty lingerie store. During my interview, the co-owner (who was a man) asked me what kind of bra I was wearing. It was creepy, but knowing that I was in a BRA STORE (and I think I even purchased said bra from THAT STORE), I didn’t hesitate to answer with the brand and style and specs. Later on I found out that all the employees (all of whom were women) had to be fitted in the store for bras and wear those bras to work at all times. (Since I’d already been a customer and was wearing their bras, I escaped that fate.) It was just as terrifying as it sounds.

    1. Allison*

      based on what I’ve heard about those in-store bra fittings often being inaccurate, that sounds horrifying.

      1. GrumpyBoss*

        You are correct. I have the misfortune of different cup sizes for my girls. It is actually my greatest insecurity, but a well fit bra makes it unnoticeable. So I never buy a bra without being fitted, since the way it gives me support and covers up my imperfections varies from bra to bra, even within the same brand/store. And those fittings have run the gamut in terms of size (anywhere from 32C-38DD).

        You know what else has run the gamut in fittings? The creepiness of the people doing the fitting.

      2. Career Counselorette*

        This wasn’t a large chain, this was a place that did custom fittings, and they were quite accurate- I really enjoyed my experiences there as a customer. Working there, however, was a totally difference experience- the owners acted like it was Waco, and that level of micromanagement and manipulation, plus the fact that it was an industry centered around women’s bodies, made it even weirder for me.

      3. The IT Manager*

        I did go to a chain store (who’s initials are NOT VS) that does bra fittings, and I was encouraged to purchase a bra that was too small. It seemed okay while trying it on, but was painfully tight when worn all day. Very disappointing. NOT going back there again and throwing their catalogs in the trash when they arrive.

    2. Chloe Silverado*

      I think I worked for the same store and it’s certainly not for everyone, but I can understand why they want employees to wear (theoretically, if measured correctly) well-fitting undergarments. If I’m a customer and I see a sales associate with very visible panty lines or a bra that is clearly ill-fitting, it would be hard for me to trust that person to advise me. That said, I think there are ways of handling this discretely and professionally, and I was not asked to describe my undergarments during my interview.

      What was more uncomfortable for me was customers asking me my measurements because they’re buying their significant other a gift, don’t know her size and think I’m about the same size. I was comfortable having a trusted female co-worker measure me, but telling a strange man my size for intimates was always SUPER uncomfortable yet we were encouraged to do so.

      1. GrumpyBoss*

        I apologize on behalf of my husband. He does that all the time (but usually for blouses/sweaters).

        1. Chloe Silverado*

          When someone asked me and was clearly mortified or overwhelmed, I totally cut them slack and did my absolutely best to help them out. I’m sure your husband falls into that category!

          On the other hand, there were some customers who’s tone or body language made it a really uncomfortable experience. It’s not really a particular characteristic I can put my finger on – there were just times when I felt kind of squicked out and couldn’t wait for the customer to make their purchase and leave the store.

          1. Cari*

            Trust your intuition and respond with what makes you feel comfortable. It is not unlikely that there are people out there who would ask the question, with that excuse, and not have actually have an SO. Um, not to be alarmist or anything :)
            (I’ve just started reading The Gift of Fear, sorry :S)

      2. Chriama*

        That’s super uncomfortable, but I’m trying to think of a way the store could offer better alternatives. Some sort of gift receipt that allows exchanges for a different size? Plastic models designed to model different sizes? It really sucks, but I feel like a lingerie store is one of those places where respectability and skeeziness really have to navigate a fine boundary.

        1. Rayner*

          Not sure about America but in England, lingerie is able to be returned, provided it has all the hygiene labels on it and tags. Usually plus the receipt or a gift receipt. It’s not impossible to do.

          1. Sarahnova*

            I’ve also never understood why a man couldn’t, you know, look at the labels on his partner’s existing bra/knickers/clothes.

            That strikes me as a lot more accurate and useful than wildly estimating her size based on a stranger’s body.

        2. manybellsdown*

          I don’t recall the place, but some lingerie store I shopped at had “gift-giving cards” that they’d hand out. You could mark down all your sizes and preferences and then your SO would keep it on hand for reference when shopping. I thought it was a clever idea.

  35. Allison*

    I could understand wanting one’s employees to dress professionally, and I can also understand why people are sometimes hesitant to say that directly – people might not know what to buy, might spend money on the wrong thing and be out hundreds of dollars on clothes they can’t wear, or people might simply not have the money for new work clothes.

    That said, this is NOT the right way to handle it. Host a fashion seminar, suggest items of clothing, send your employees to Corporette, tell people where to go for cheap clothes or even give out gift cards if you want to give them a “treat” or help them afford new clothes, but this looks like straight-up micromanagement even without the underwear issue. Is she worried about visible panty lines or something? Because I can’t see how you’d know if someone’s undergarments would be an issue just by looking at it.

    1. Loose Seal*

      I am willing to be that the “looking” at the underwear was so that she could approve plain-Jane underwear. Since she was footing the bill, she probably wouldn’t want to buy sexy underwear.

      All my opinion, of course.

  36. ThursdaysGeek*

    What only a few have touched on is what I see as the greatest issue. She is treating her employees as children who are unable to even pick out their own apparel. Is she doing something similar with work tasks? Does she treat them as professionals in any part of the job? Or is she the mother with her children employees, helping them in all sorts of tasks? I would recommend the friend look more closely at the rest of the job, not just the shopping trips.

    1. Chriama*

      Is that really the greatest issue though? Between a boss who micromanages you and a boss who wants to approve your underwear, I feel like 1 conversation is definitely less awkward to have than the other. However, it seems this is a small family-owned business and the boss is the owner’s wife, so there’s probably a lot of boundary-crossing, some of which would be more tolerable to people.

    2. Parfait*

      I don’t even want my own mother approving my underwear purchases. She didn’t even do that when I was a teenager, just gave me money and sent me off to the lingerie department.

  37. TotesMaGoats*

    I’ll agree that this really tips the scale into weirdo-ville but honestly if my boss (any of the ones I’ve had) was taking me shopping for nice stuff on the regular, I wouldn’t bat at eyelash. But that’s me. My boundaries are fairly flimsy.

    My real concern for this person revolves are what might happen if this person tries to leave for a new job. Can we say emotional blackmail? Or for that matter, actual blackmail. I would suggest being very careful when/if she does decide to leave.

  38. Anonylicious*

    She needs to update her resume and run, not walk, away from that festering pile of not-right.

  39. Stephanie*

    Ick, the creepy thing about this is that the manager’s scrutinizing employee’s bodies this much.

    “Jane, did you finish the quarterly report? Also, you should really increase your band size and decrease your cup size.”

  40. TeaBQ*

    You know I’ve read of things like this before, but only in stories with a funky soundtrack and in offices with copiers that were constantly in need of repair…

  41. Annie O-Nonymous*

    If you ask me, this smacks of sexual harassment.
    I’ve had former employers subtly and not so subtly hint that I don’t know how to dress myself. Considering that I’ve been working 30+ years, and those were only two employers, I’d say they were in the wrong. I’d totally resent that kind of interference.

  42. Scott M*

    I would LOVE to hear the other side of these stories. I really, REALLY want to hear the justification for this from the boss. Seriously. Why do people think that this sort of stuff is acceptable?

    1. Katie the Fed*

      I know. I’d really love to hear a recording of Alison interviewing this woman.

  43. Fhyl*

    I can’t help but feel like you ARE giving her a free pass on behalf of being female. I feel like you would have advised to bring the issue to HR in a heartbeat if the faulty boss had been a man, possibly even without taking the underwear incident into account.
    This is, indeed, super creepy no matter the genders involved, but I get the impression any man attempting this would be covered in sexual harassment lawsuits within a week.

  44. Chewbecca*

    While I would love someone to say “hey! Free money! Go buy new clothes!” It would really make me uncomfortable it it were my boss.

    Plus, we’d have problems if she tried to dictate which stores and departments, because I’m a special snowflake* and it’s really hard for me to find clothes that fit.

    Unless she’s sending people to Anne Taylor or Banana Republic, which have awesome petite clothes with no elastic waistbands in sight. Just because I’m short does not mean I’m an old lady!

    *Like probably 90% of the rest of the people on this site.

    1. Stephanie*

      Although with bras, you might have employee special snowflake situations. The options for those with bigger busts are expensive and limited.

      1. Chewbecca*

        I know! I can pretty much only buy from Nordstrom or Dillard’s. I doubt boss lady has $70+ a pop budgeted for bras alone.

        1. Simonthegrey*

          Around here, not even Dillards has bras that fit. I shop at Catherine’s. I’m not even that big in the waist (their pants, tops, etc. are all too big for me) but they’re the only place I find 44 DDD bras that I can try on. I’m leery of buying bras online just because I’m very picky about what the fabric feels like, strap width, etc.

          1. Kerry (Like The County In Ireland)*

            Not to buzzmarket, but $5 shipping, free returns and they carry European bras. I find that to be key–American lingerie at once wants to shame you for having big boobs by making it hard to find bras, but also exalts big boobs.

            1. Carrie*

              Sorry to get off topic, but I feel your pain. I also have to buy European for the same reasons. is another site with lots of sizes and European brands.

            2. Zillah*

              I had a bad experience with trying to return bras to figleaves – it was several years ago, but it took them months to refund my credit card. :/

            3. Rayner*

              Bravissimo in the uk. Super comfortable and long lasting. A little pricey but they last forever. I wore two for a year straight while I was in uni because I were big boobed and broke and they lasted well.

            4. the celt*

              I shop at (I only wear bras that have UK sizing, because they seem to have a better system than the U.S.) or (this one is in the UK like When I finally realized that most American companies do not have the right size for me AND I realized that they would fit you into something that wasn’t really the right size to sell you something, I did some research and found my correct size in a UK brand. I now buy a specific brand that I’ve come to love (Elomi), and I’m confident that I’m getting one that will probably fit, give or take a band size.

      2. Career Counselorette*

        I almost wish that specialty bras to wear with my specialty business casual clothing so that I don’t look terrifying with my specialty DD+ chest in this specialty clothing I am mandated to wear WAS something employers would cover. Not pick for me and inspect, just cover.

  45. TL17*

    Maybe I missed this part, but does the boss then require the employees to wear that clothing to work? And if they don’t, is there a consequence?

    Also, how could this be enforced re: the underwear? I have a feeling this could get more creepy.

  46. iseeshiny*

    Well, hey now, let’s not be too hard on the boss. It may be her sincerely held belief that her employees must be wearing the correct undergarments and therefore her legal right as the owner of a closely held company to make sure that her funds are not being spent on the wrong underwear. We can’t violate her rights as an employer just because some lady thinks she has the right to pick out her own bras.

    1. Career Counselorette*

      The day a company tries to appeal for this is the day I leave the workforce and go live in the woods to forage my own food and make potions.

  47. Anon Accountant*

    What if an employee doesn’t wear underwear typically?

    Or if a certain style they prefer doesn’t conform to what their manager insists on purchasing for them? Or if the manager doesn’t tolerate the employee saying “I’ll buy my own underwear”?

  48. Jess*

    I temped in a place once where my (female) boss bought one of my coworkers (a temp as well) a dress once, apropos of nothing and I thought THAT was boundary-crossing. Boss and coworker had this weird narcissist/enabler co-dependent relationship going on where they hated then adored each other on alternate days. Coworker thought there was nothing amiss about this or the dress.

    People are insane.

  49. HR Manager*

    I’m sorry, but unless this person works as an underwear model or a stripper, I don’t see how underwear is ever the business of the company (unless it’s showing, and a conversation has to be had about how inappropriate that is).

    Whether this person is interesting in her or not, this sounds like sexual harassment and/or gender discrimination. Does this woman go buy boxers/briefs for the male employees too? If I make sexual jokes in the office, that is harassment and a hostile work environment, even if I don’t see her as a BF/GF. Management having conversations about her underwear seems far more invasive and hostile.

  50. Tinker*

    I kind of wonder what sort of behavior would ensue if I took such a person up on their offer and promptly put in an order for five binders, some compression shorts, and a custom suit… Got a feeling it would be amusing, particularly considering the existing “homosocial enforcement of gender norms” vibe I’m getting here.

  51. BritCred*

    My only consideration as to *why* this might have been done legitimately? Because I’ve seen office underwear bad options….

    Aka, the estate agent who wears leopard print bras under sheer white tops and its so bad it shows up in the photo they took for the website for her. Let alone in person.

    So therefore I could see this to an extent: specify that undergarments should be discrete and not able to be seen or detected (say over lacy or over adorned to produce bumps) under the outer layer of clothing. And specify that the outer layer should be non sheer, non see through under all lighting conditions.

    Going and helping them PICK the underwear? Nooo……

  52. JustCallMeVic*

    This is one of those submissions I refuse to believe is actually true. I think the OP just wanted to see if she could get Alison to publish her letter. I’m going to try that next with a story about “the boss who refused to wear pants.”

    1. Ali*

      I agree. I’ve always wondered if Alison gets fake letters. This one has to be up there as a possible phony…right?

    2. Ask a Manager* Post author

      I think it’s true — in part because I had an exchange with the OP where she (a) used her work address and (b) didn’t have answers to some of my questions (whereas I think a fake letter-writer would have made up answers).

    3. Pennalynn Lott*

      I definitely think it’s true. I work for a small, family-owned business and the owner’s wife is completely boundary-less. She has never worked in a professional business environment (went from living at home to living in her husband’s home to being a full-time SAHM) and treats the employees like children and/or confidantes. She is racist and homophobic, and the stuff that comes out of her mouth should be legally actionable. . . but she phrases it in terms of her religious beliefs (yes, she feels she can justify racism based on her “sincerely held” religious beliefs) so there’s nothing that can be done about it. [Thank you, right-wing Supreme Court justices.]

      1. Observer*

        Please don’t paint all SAHMs with one brush. I know a fair number of them, and NONE of them would ever be this boundary-less. And, by the way, “sincerely held religious beliefs” are not a simple carte blanche for any sort of bigotry, Hobby Lobby notwithstanding.

        However, it’s worth noting that bigotry, even extreme sorts, is generally not actionable unless you can tie it to specifically illegal actions.

    4. Cara*

      I am always skeptical of the “I have a friend who…” letters. I just assume that either the OP is actually the “friend” or a lot is getting lost in the translation. The letter may be accurate according to the OP, but the friend could be embellishing or there could simply be details that are interpreted differently in the retelling.

      Here, I’m especially skeptical of the account that 1) the boss told multiple “gals” to go to a department store and pick out particular items, 2) the boss went to each department of the store individually to look at the items on hold, and 3) the boss scolded the letter writer’s friend for making her go out of her way to check the lingerie department when there was nothing on hold there.

      If you go to a department store and pick out items from multiple departments, you don’t have to check out individually at each department. That’s the point of a department store–you can check out at a register in any department. So I am really skeptical that they would keep all of the items segregated that way and make the boss go through the store department-by-department, flagging down a salesperson from each department–it just doesn’t make sense.

      And IF the boss did indeed have to go to each department anyway, there was no reason to scold the OP’s friend for not picking out underwear because presumably some of the other women who went on the shopping trip picked out underwear and thus the boss’s trip to the lingerie department was not wasted.

      1. Jade*

        I read this differently – it sounded like the boss checked all the holds in one area; didn’t see underthings from the OP’s friend so went to the lingerie dep’t specially to see if the hold items were there and found nothing, to her great disappointment.

    5. Lizzy*

      Speaking of bosses sans pants, I once caught a supervisor in his boxers. It was a Friday and he thought everyone went home. Don’t presume it isn’t true just because it sounds crazy. :D

    6. DMouse77*

      FYI, the OP is actually my own boss – I got her started reading AAM in recent months, and when she told me this story about her friend’s situation, we both agreed that she should send it in!

      1. smilingswan*

        Can you tell us what type of business/what industry it is? How many employees are there? Are there any male employees? Do they also get new wardrobes/underwear? Enquiring minds want to know!

  53. Frances*

    So I don’t think I’ve seen anyone bring this up yet — when are these shopping trips taking place? Because this entire situation is bad enough, but if I’m also being expected to give up some of my free time to let my manager dictate my wardrobe, I will just be unfortunately very busy every weekend/evening right up until the day I find another job.

    1. First Time Commenter*

      Yeah, seriously. I’m a lady who absolutely hates shopping for clothing of any kind but especially office drag. You’d better be paying for me to go through this torture or gifting me time off for doing it.

  54. MaggietheCat*

    At one Ex Job – The VP thought that people were using too much TP and asked the admin to remove all but 2 rolls at a time from the unisex shared restroom. A few months later the office had an expensive plumbing fix (it was an older building) and VP decided that people were STILL using too much TP and had the admin order wipes instead. Yep, replaced TP with wipes because they ‘flushed better’. People had to smuggle their own TP in their pockets each time if they wanted to use it.

    1. Stephanie*

      Wipes?! Those have been shown they don’t break down as well as TP. Those would make the plumbing problems worse…

    2. BritCred*

      I did have a boss who would have meetings standing outside the Gents bathroom. Why? Because then he could check who the phantom mess maker was…..

  55. SouthernBelle*

    my old boss liked to shop… and she’d often go out shopping and take us with her (small staff – it would be no more than 4 of us at any one time)… there was one young lady who worked with us who’s clothing was less than desirable… often too tight, ill-fitting, low cut, old trends and overall sloppy… my old boss took on a more maternal role with her and i can totally see her leading her into the lingerie department and urging her to pick out underwear that fits…

    now this manager, i don’t know…. the approval part is what gets me…

    1. Biff*

      Context could change this dramatically, but I’m getting the impression that this just straight up creepy.

  56. EG*

    Wow. This is the complete opposite of my company’s owner, who wanted to show appreciation for extra hours that I and a coworker had put in to cover an unexpected turnover. He gave us the company card (with a nice budget allowance) and instructions to go shopping for 2 hours for work clothes, but specifically said no lingerie or underwear.
    Of course, I’d have preferred a smaller budget and a full day to wander the 3 area Goodwill stores, but that’s just me.

  57. Stephanie*

    Another thought just came to mind.

    Alison, do you happen to know what kind of business this is? Reason I ask is because I could see the owner’s wife wanting to buy clothing for the employees if this business was some sort of professional services type where a really polished look was expected. I’m thinking along the lines of high-end real estate, personal shopping, etc catering to high net worth individuals who would expect a certain look. Of course, the less-creepy way to do this would be to provide guidelines and a clothing allowance or raise.

  58. No name, no state*

    This is SO WEIRD.

    And even though this is not quite the same thing, it reminded me of the day a close male colleague’s wife (about my mother’s age) who is a good friend took me shopping for my brother’s wedding. She wanted me to get a certain type of bra (in a style I was embarrassed to wear) and then was showing me the skimpy panties she was considering purchasing.

    “Check please.”

  59. dangitmegan*

    Oh my. It’s awkward enough when I have to take my dancers bra shopping and approve their choices for under their costumes. Not that they care since they just strip naked at the drop of a hat. But still that’s something that I have to do and it’s weird.

    1. joey_aam*

      One small benefit of not being well endowed was I had no troubles with this! All I needed was something stretchy in flesh color with a clear back and clear straps. Not like some of my fellow dancers who had to special order bras :(

    2. BritCred*

      Yeah, we get to a level whilst doing cosplay and reenactment – seeing people in their underwear is so usual we most likely won’t even twig we’ve seen it.

      However the time that one person starts a “give the lady some privacy” because another is near darn drooling over a changing cosplayer (and she wasn’t even in anything skimpy – she was practically swimsuited under the costumes) we all felt darn bloody awkward.

  60. Carrie*

    This story is probably one of the craziest I have ever read. I think it is invasive, creepy and I do believe this is a form of harassment. The boss is essentially demanding to see your bra and panties…..doesn’t matter the gender, this is odd.
    If this boss is so concerned, then all she has to do is write up a dress code for the employees. If she feels the need to include underwear, then she could have wrote something like “employees must wear undergarments that are well-fitting and that will not show through clothes” or something like that. To actually make you go to the store and then approve it? Wow. Honesty, I’d rather wear a uniform then have my boss approve of my personal clothing choices.

  61. Vera*

    This is way out of left field…but maybe the boss has a fetish for playing dress-up? She is treating her employees like barbie dolls. She goes and picks out the clothes and (presumably) the employees wear them to work and she gets a high from that. Pervy? Absolutely. This idea totally creeps me out.

    For me, this explanation makes WAY more sense than the boss just wanting them to dress professionally, and would explain the extension of the shopping experience to bra & underwear. Even if she won’t see them wearing it, she gets to buy clothes for her barbies.

    (Also, maybe I’ve been watching too much Law & Order.)

    1. Relosa*

      I don’t think so. My boss has never crossed a line like this that I have witnessed but he makes so many comments on my clothing and “treats” us so to so much when he is in town, I wouldn’t put it past him. Or his wife, who is also my boss.

  62. Sadsack*

    Something just occurred to me. The boss went to pick up the clothes for the employees, so she would have presumably brought the clothing in to the work place to hand them out. So I guess that means the boss would have taken the employees’ undergarments home with her first. Eww. So weird.

  63. Angora*

    This is odd but I wonder one of the employess is not addressing appropriatly (like no Bra) or clothing so tight you see every bulge or underwear line, etc. This the boss’s way to address it versus having a discussion with the employee. I had a coworker / roommate years ago that wore things too sizes too small and ill fitting bras. They had a meeting and dicussed the dress code with us at work. We got home and my CW/RM was like, who are they talking about, cannot believe someone dresses like that. Totally over her head.

    I think what should be done, if she wants her employees to dress nicer, give them a gift card and a purchasing guideline and forget it. If she’s going be that picky, she should choose a standard uniform … black skirt / pants and blouse for example and forget it.

    Also wonder if the boss wants someone to shop with … her way of purchasing a shopping buddy?? Unable to make friends to shop with .. so I bully my employees into playing the role?

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