knee-high boots and business casual attire

A reader writes:

I know you answer mostly work behavioral questions, but I have a question regarding attire. I work at a hospital (not as a health provider) that requires business casual attire. Now that the weather’s getting really chilly, I want to wear boots, knee high boots in particular. I’m not talking about patent leather, spiky heel, thigh highs, but just a tall boot that helps keep the legs warm. Something like the ones here. What is your opinion on boots for business casual attire?

If only you knew how very much not equipped I am to answer fashion questions. And the last time I answered one, I had to shut down the comment section (a historical first) because things became so contentious

But in any case … in general, I think that knee-high boots are totally appropriate for business casual, as long as you’re not wearing them with a micro-mini skirt. (They can also be appropriate for more formal environments. Check out this picture of Condoleeza Rice.)

However, the ones you linked to in particular are over-the-knee boots, which I think takes them into a different category of edgy, one that’s too much for a lot of business casual environments. But if they stopped at the knee, I think you could wear them without any worry.

Anyone want to present an anti-boot argument?

{ 30 comments… read them below }

  1. Kat*

    I think boots are perfectly appropriate for most workplaces, especially business casual ones. Even the over-the-knee boots in the photo could work in a more creative environment, though I would wear them with opaque tights.

    –Kat (editor,

  2. leatherette*

    I think the way you wear your boots is most important. I work in a very conservative office but on jeans days, I pair my knee high boots with skinny jeans and a sweater. I would not wear tall boots on a business casual work day here unless it was under a longer skirt like the pic of Ms. Rice (which is very 90s so I wouldn't do that anyway). Hope this helps!

  3. Alysia*

    I think as long as your skirt is closer to knee-length than thigh-length and your books are mid-calf to just under the knee, you're okay.

    A coworker of mine at a previous job wore mid-calf boots with thigh-high stockings and a miniskirt to work one day. She looked ridiculous!

  4. Jamie*

    I think they're fine if you're wearing them with a longer skirt or pants. Although if you wore them over pants they would look like riding boots – an interesting style choice for work.

    But a skirt short enough to show leg between the hem and the top of an over the knee boot? That's a little bold for work…but it would give the office hall monitors something to gossip about.

  5. kristinyc*

    I wear leggings with knee-high boots and slightly above the knee skirts all the time- but I a) have a very casual dress code at work and b) work in NYC. I think if you pair it with dark tights/leggings and an appropriately long skirt, you can make it look professional. Or, find some nice black skinny pants and wear a longer shirt (a longer button up with a sweater vest over it might be cute) with it.

    I have a knee-length tweed tulip style skirt (fitted at top and flares out at the bottom) that I wear with dark leggings, boots, and a button-up shirt, and that looks nice in the winter.

    The ones you linked to are pretty tame (and cute!), so you should be okay.

  6. J.Lim*

    I will definitely try out different combinations of hose, pants, skirts, and boots to see which ones can pass for business attire. I'm glad I got the green light to try it out

  7. Anonymous*

    I actually have those exact boots and wear them all the time to work, usually with skinny black pants and a tunic-style top…however, I also work in web design for a nonprofit, so it's not a hardcore business wear required type of environment. I don't like to wear them with skirts to work, only because I'm on the shorter side so the skirt would have to be shorter as well (but I will wear an outfit like that out!)

  8. Cosmic Noodles*

    I'll go with the consensus here and give the stamp of approval of the knee high boots!

    I also encourage you to branch out of the world of flats as well – a heel and almond or pointed toe can be pretty and professional.

    Just make sure you balance out the sex kitten factor with the rest of your outfit, and opaque tights or leggings are your friends!

  9. Abby*

    I work in higher education and I wear knee high boots with my suits. I think it looks sharp and there is a gap between the bottom of my skirt and the top of my boots. Just yesterday I wore them to meet with two CEOs of the hospitals in town. I think it was fine.

    I also wear boots with my longer skirts and on casual days I wear knee high boots over my jeans.

    I think it is fine.

  10. Anonymous*

    I think your guide should be what you see in your office when you look around. No more or less than that.

    As an example, if everyone in the office wears shorts and flip-flops, then yes, boots and a skirt would be inappropriate.

    Dress for the job you want.

  11. Anonymous*

    The fact that you felt compelled to ask whether or not the boots were appropriate leads me to believe that either you have doubts about them or someone else may have mentioned something.

    My suggestion is find another pair of boots to wear to work. Problem solved!

  12. Lisa*

    I think it depends on the boots. I would happily wear plain black or brown, structured, heeled knee boots with a suit even for a corporate environment. Boots of another colour, or with hardware (buckles/studs), calf-length, flat or slouchy boots… well, I'd take a view depending on the rest of the outfit and the combination of the above, but probably I would keep for business casual, and business casual with skirts – trousers tucked into boots I would consider a casual look.

  13. IndigoSH*

    I have boots just like the ones in the picture and I have worn them to work before. I do it with a knee length skirt and tights or either stirrup (sp) pants and a blazer. It works. You can be professional and fashionable at the same time. As long as the heel is flat it's fine. If they had a heel then I'd have to say to save them for after 5.

    I also work in a non-patient care health environment. (just like the OP)

  14. Anonymous*

    I work for a Fortune 500 company in the Midwest, and it's a mix of business/business casual. I see heeled knee-high boots all the time (even on our VPs)–it looks professional and fashionable. I think the key is that you shouldn't have a lot of skin showing. If you're wearing an above-the-knee skirt, you should probably be wearing opaque tights or leggings.

  15. Anonymous*

    When in doubt don't wear it.

    No one on this site can tell you what's appropriate attire for your business. Even business casual & dress down have guidelines.

  16. keepiingitreal*

    Seriosuly, people the boots are called Tally HO's for goodness sake! When I think of thigh high boots (check the description) Pretty Woman comes to mind and that is certainly not an image you want to portray at work. Yes, if you are in the fashion industry than maybe, just maybe this works. But, in this case I say "hell to the NO" Also, in the future if you have to ask then it's likely you already know the answer.

  17. KellyK*

    I think that knee-high boots in general are fine. I wear mine to work, and a few other women do as well. The over-the-knee boots posted are a bit much, though, in my opinion.

    But everybody has drastically different ideas of what's appropriate. If you see a few other people at your workplace wearing them, you can probably go for it. You can also ask your boss.

  18. Rebecca*

    I'd say they're fine as long as you don't cut corners on any of the rest of the outfit — keep other stuff fairly conservative, wear some nice accessories, etc.

    If they had much of a heel I wouldn't do it, though. Where work clothes are concerned, it usually doesn't work to push more than one boundary at once!

  19. What the?*

    May I add, neutral colored Knee high boots definitely ok…Fushia, or green, yellow and any other screaming loud color, definitely not ok!

  20. Anonymous*

    To be honest, I think it looks tacky, especially in a hospital type enviornment. Well, let me rephrase that. It really depends on how you wear them, but the "style" these days seems to be wearing them over pants, and that just looks incredibly tacky. Even the pic of Condolezza Rice looks a bit tacky.
    But, as someone else said, if you're asking about them, then you have doubt, and when in doubt, don't do it.

  21. KellyK*

    Oh, also, if you decide against the boots, or want more options, I've found that leggings under pants are a nice way of keeping your legs warm. A lot of dressy pants don't seem to be designed for warmth. Tights or leggings (probably dark neutral) are also better for keeping your legs warm with a skirt than knee-highs or pantyhose, which seem to do nothing whatsoever. (I know, I know, pantyhose are a holy grail and if I'm not a dancer, I shouldn't wear tights. :) )

  22. Jane*

    I wear boots to work in an office environment most days during the winter months. Mostly black just below the knee with an office suit skirt. My skirts are normally a couple of inches above the top of the boots. On casual days I wear knee high boots over skinny jeans – contrary to some comments on here this is a good casual look if you’ve got the figure for it and an expensive pair of boots

  23. Mack*

    Work fashion faux paux alert!!! Oh my! How was there only one person that said “no?” I say “no no no” to boots in the workplace. Unless you work on a farm. Then it is probably best you wear boots. I also say “no no no” to leggings in the workplace (being pregnant is the only exception to this rule). Call me old fashioned, but boots in the workplace are quite tackey. Don’t get me wrong, I looove boots. I have theories on the perfect boot-wardrobe per personality type. I, like many women, have trouble not buying every pair of fabulous boots I pass in the mall. But just as you shouldn’t wear your ratty weekend t-shirt to work so should you not wear the trendy leggings and/or boots to work. Dressing appropriately for work does not mean being trendy. Dress for success ladies! Unless you don’t care about success. In that case by all means, wear the boots and throw in the leggings while you are at it.

  24. Just A Guy*

    I think wearing boots in the office is fine and actually fashionable. When I see a woman wearing boots, it tells me that she has taken an extra few minutes to accentuate her appearance. In what can seem as a rush-rush time, it is refreshing to see that a woman has taken those extra few moments to look nice in her own individual way. Not only does it make her look good, but it brightens any office or work setting.

  25. Jody*

    I actually love fashion and used to work in a tax firm. I am quite slender and small and used to wear leggings with knee high boots, sweater dresses or longer tunics all the time because it was comfortable and I loved the look.
    Unfortunatly, I got pulled aside a couple months later saying that people were complaning about my dress attire and thought I looked like i was going out drinking or to the bar… and this is coming from a office where most were over weight — mid life women that wore boring loose black dress pants asnd large flowing floral shirts.

    ALl the younger students that this company took on also wore what I did but I was still told that I could no longer wear standard stockings, leggings or boots or even sweater dresses anymore. DISCRIMATION!

  26. Hallo Franki*

    I also work in a non-patient medical office in San Francisco. Two words: Eternal FOG and pretty chilly most of the year. Needless to say, I wear knee high boots A LOT — and yes, to work. Obviously, when I have meetings with the CIO or or something, I am a bit more on the conservative side only because…well, they’re old fogies and are warriors of the ‘women-should wear navy pant suit’ days. I even have some over the knee boots that I wear. They’re not thigh-high (they’re the Stuart Weitzman 5050 boot) and I’ve received many compliments on them here at work. They end just above the knee joint (granted I do have longer legs…so more petite women, BEWARE!) and they have a flat heel. Though, when I do wear them, I try to balance out the rest of the outfit more conservatively (think simple tunics and longer blazers).
    However, I will say…I live in a metropolitan area (San Fran) and I feel when you do live in a more lively, hustle and bustle city…people tend to be much more open minded and bold when it comes to fashion and the corporate work place.

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