Over-the-Knee Boots at the Office?

otk boots for workWhile doing our round-up of knee-high boots, I was struck by how things have changed in such a short time — when I first started this blog, knee-high boots were still pretty scandalous, and over-the-knee boots (or OTK boots) were completely, totally risqué.  Cut to today, and they’re EVERYWHERE — flat versions, high-heeled versions, on most best seller lists, with rave reviews from everyone from 20-somethings to 60-somethings.  I know Jean at ExtraPetite has talked about wearing her 5050s for the commute, but I thought it might be interesting to have a poll: are over the knee boots so omnipresent that you can wear them to work? (Pictured: Screenshot of the Stuart Weitzman 5050 from Zappos, where they’re $635; they’re also at Nordstrom for the same. Here are a few under-$200 alternatives.)

As always, you have to know the specifics of YOUR office.  But because a poll can be fun, I thought we’d have this in two flavors: one poll for folks working in conservative offices, and one folks for the women in business casual offices.  Just for ease of discussion, let’s define a “conservative office” as one where, on any given day, 30% or more of your coworkers are in suits.

Conservative Offices and Over the Knee Boots

Here’s the poll if you work in a conservative office (see definition above… multiple selections are allowed; click here if you can’t see the poll):



Business Casual Offices and Over the Knee Boots

Here’s the poll of you work in a business casual office (multiple selections are allowed; click here if you can’t see the poll):

Ladies, what are your thoughts on over- the-knee boots at the office — would you wear them to work?


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over the knee boots for work


  1. Kat, this is a great pole, but we could NEVER get away with boot’s like these in the office. The manageing partner does NOT even like me to wear slack’s or tight’s in the cold of WINTER, as he INSIST’s on being abel to see my legs. That is why he reimburses me for 4″ heels but skowle’s if I want to wear flat’s. Also, Frank insists on closed toe shoes and dresses and he always likes to stare at me. Even the judge is the same way. My mom says that all men born before 1950 are like this b/c they remember some of the big movie star’s like May West and Ingrid Berman who had great leg’s and men alway’s dreamed about having sex with those women, with their long legs and all.

    I don’t know what all the fuss is with leg’s but it is harmless enough to let the men oooogle me if that is what they must do to get through the day! I say YAY to reimbursement for clotheing as long as I find the clotheing to be fashioneable, who care’s if the men stare at me! I hope the HIVE will get their manageing partner’s to reimburse them for all clotheing, but what I have is a good start.

    I got a good recipe for Pumkin pie from the INTERNET, and Myrna is goeing to stop off at Fairway’s to get the ingredeants so that we can bake BOTH pie’s together, but at MY place b/c I have a new stove that I hardly EVER use! YAY!!!!

  2. Can someone please explain the character that is Ellen? I’m so confused.

  3. TO Lawyer :

    I actually used to think they were risque but I saw a really nice flat pair on the weekend and now I really want them – I feel like they could be really versatile (although I’d skip them for anything too formal).

  4. Anonymous :

    We’re on the casual side of business casual (people occasionally wear jeans on random non-Fridays and everyone wears them on Fridays; nobody wears suits) but I think OTK boots are totally and completely unacceptable for work. I’m not sure why I have such a visceral reaction to them but I think it has to do with the fact that they come across as overtly $exy and $exy and work are two words you never, ever want to associate. I do like the look for the weekend but don’t spend enough non-working hours in anything other than sweatpants & leggings to justify purchasing a pair.

    • AnonymousAlso :


    • Senior Attorney :

      Yep. I tend to push the boundaries for office wear, but OTK boots seem like they’re well on the wrong side of the okay-for-work line.

    • Agree with this. We’re not conservative by Kat’s standards — maybe 20% or fewer wear suits on a given day, and usually only on court/meeting days; jeans on Friday and sometimes other days; some people wear legging with a tunic sweater, etc.

      However…. OTK boots will always be very “Pretty Woman” to me, and as a result I associate them with a *different* profession. I’ve seen OTK boots worn very cutely in a casual context, but would not find them to be appropriate for a lawyer at my firm.

    • Agreed 100%. OTK boots scream trashy. Maybe they are ok for casual days at a strip club, but not in an office!

  5. Ahoy, matey! :

    Only OK if you work in an office that is Pirate Casual.

  6. My office is business casual, and I sported a pair of black leather just barely OTK flat boots with black tights and an appropriate length pencil skirt and crew neck sweater. I received several compliments on the outfit from the women in the office. I think there is a fine line when wearing this style of boots before people start thinking of Pretty Woman. I chose to wear them with the tights so that it was not quite so obvious where the boots ended and the tights began and chose a skirt that also ended around my knee. I’m also 5’9″ and the OTK boots look a lot sleeker on me than boots that end several inches below my knee. I think the key to wearing them at the office is 1. the material that the boots are made of and 2. what you choose to wear with them.

    • Hollis Doyle :

      I was going to make a similar comment re: height. I’m 6′ tall, so knee high boots don’t usually actually reach all the way up to even the bottom of my knee, creating a gap between the bottom of my mid-knee length skirt and the top of my boots. Although I don’t have any OTK boots, I can see how they would eliminate the weird gap and not be so noticeable as “OMG you’re wearing OTK boots” on someone tall with long legs. That said, I’m not sure I would feel the same way about heeled OTK boots. that’s still veering into Pretty Woman territory, IMO.

    • LilyStudent :

      I’m also 5′ 9″ and my ‘knee-high’ boots come some inches below my knees. Sounds like some barely OTK boots might be worth trying, thanks!

      • It took me a while to even understand this “knee high” boots concept I kept reading about on Corporette because I’m 5’11” with long legs and boots that length are 2/3 up my lower leg. I’ve shopped and researched like a mad woman looking for OTK boots that actually do go over my knees because I’ve wasted money on pairs that hit below my kneecap. SO fyi if you’re wonderingbeing 5’11” with a 34-35″ inseam in flats, the Louise Et Cie boots that Kat linked to go over my knees. My favorites are Chinese Laundry Riley. They also go over the knees. The leather isn’t as nice but I prefer the overall fit better. Also Steve Madden Erupt but they are less fitted at the top at least on my legs. I’m not joking I tried about 5 different pairs last year. I couldn’t spend that money on the SW5050 boots on principal.

  7. Agreed. I do the same. I am tallish, wear black tights with them, and they hit the middle of my kneecap, so not totally OTK.

    • Same here – I just see them as knee-high boots for tall people. But I also agree that I wouldn’t wear actual over-knee boots to work.

    • Miss Behaved :

      Yeah. I voted no for actual Over the Knee boots, but I own a pair. On me, however, they only come up to the middle of my kneecap.

  8. elemenopie :

    I have never considered OTK boots mildly attractive at all.

    Despite their appearance in modern fashion, they still read a little unsavory and pirate-y to me to even work in my very casual office–casual defined as someone else above did: jeans any day of the week, no suits.

    I +1 to the comments about “other professions” and “visceral reaction”

    Of course, I’m short, so OTK boots would be very clearly OTK for me.

  9. lucy stone :

    My department is business formal, our building as a whole is business casual. I just can’t see these being appropriate for work unless you are the Dread Pirate Roberts…the heeled ones read too sexy, the flat ones read too Knights of the Round Table.

  10. I was actually having this debate in my head earlier this fall. I love the way they look when they’re flat (I still find the heeled version to be a bit too Pretty Woman, opening sequence), and I would wear them outside of work in a heart beat. But, at work, especially on someone not very tall, I think it can get tricky. You can’t really wear them with pants unless jeans/leggings are okay in your office, which is def. not the case in mine. And for most people, I think these type of boots look best with a shorter more flared skirt, which also wouldn’t work for a lot of offices, certainly including mine. I actually did see an intern wearing a pair very similar to the ones pictured to work (with a mid thigh, skater skirt and a black blazer) and while she looked fantastically cute, she def. did not look “work appropriate” for my work environment. So, yeah, a know your office kind of thing.

  11. Even in super-casual Silicon Valley high-tech, I hardly ever see OTKs at the office. I can imagine them for Fridays, flat, with skirts & thick tights in the same color (say, all black) so it looks more mod or wintery & less trampy. But I still haven’t seen it. Not sure that I’d do it, but that’s more bec. I’m short & curvy & I don’t think it would look great on me. Knee-high boots with or w/out heels are standard for the office tho.

    • Keilexandra :

      I’m also in super-casual Silicon Valley tech, and I’ve seen OTK boots on two different women in my office. One is a eng contractor who frequently wears leggings and questionably work-appropriate outfits to work, but the other is a fashionable product manager who’s in meetings all day every day. I think flat OTK’s are much more appropriate than even a kitten heel, though.

  12. I don’t think they’re office appropriate at all. I’m 25 and I’ve been wearing them for years. I have about five different pairs that I wear regularly in a casual, outside of work setting. I don’t like to wear heels, so I often wear them with dresses for a night out in the winter.

    I’ll also say I think Extra Petite is crazy for commuting in $600 boots when you’re just going to take them off when you get to work. I’m in Chicago though so if I need comfy commuting shoes, its Sperrys in the warm months and probably Sorels/Uggs/Hungers in the winter months. I’m just envisioning those gorgeous boots walking through piles of salty slush. No.

    • I think it depends on the weather. I think she’s in Boston, which is not too dissimilar from NY in winter. Maybe slightly less nice, but for the last few winters on all but very snowy/slushy days, I’ve commuted to work in a knee length DvF pair of black leather boots and they’ve held up fine. I took them to get weather treated when I first got them and then for upkeep every subsequent winter. What’s the point of boots if you’re not going to wear them?

  13. So I may have cyberstalked by bf’s ex today, and I found out she’s engaged. Is it terrible that I feel super giddy about it for no real reason?

    • I would wait till she was pregnant to celebrate.

      Joking, of course. We all have those moments. I would just try to not make a habit of it (e.g., do not look at her bridal registry) because that’s a rabbit hole that can be hard to crawl out of it.

  14. So…I am a super-duper longtime reader of this blog, and I am sure I posted some “HECK NO!” comments regarding boots. I am from SoCal, and when I first started working, knee-high boots were always worn by support staff only. So…whatever. I will never forget the candy apple red knee high boots that a recruiter wore at my Super day for banking in NYC…a million years ago. So trashy. (Fine for clubbing…not fine for the office). I will be on Team No Boots or Team Only Very Tasteful Boots forever. Sorry not sorry.

  15. I used to be firmly in the “not appropriate” camp….but then I found a lovely pair of Cole Haan OTK flat boots for only $30 at my local consignment shop.

    I wear these boots multiple times a week to work now. Sometimes every day of the week. I wear them with skinny jeans tucked in and an untucked button down shirt or sweater, perhaps a vest over the whole ensemble. This look does not say sexy at all to me…in fact I’ve gotten comments that it makes me look like a [my job] superhero. Which I kind of am;)

    • This is exactly how I wear my OTK boots at my very business casual law firm. Mine are flat, cognac color matte leather and very sleek. I only ever wear them on Fridays, with skinny jeans tucked in and a long, flowy button down, maybe with a sweater or cardigan on top. I think it works and doesn’t look too sexy or flashy at all. It’s actually a very preppy, equestrian-esque look.

  16. I wear a pair of black flat boots *beneath* my black pants (not hugging at all). It looks similar to regular black shoes. I prefer this no-show wear , because I wear boots for warmth during commute, not for the look. I think the pants-over-boots wear might be less distracting and more appropriate for work.

    But, I work in education – I am not sure how conservative education compares to the typical firm. There are people wearing suits, but we assume they have moved from research to administration, are meeting the Dean/ Provost that day, or it’s a first day of class. I have a colleague wearing light brown heeled boots, blue jeans with patches tucked in, even on the teaching days(!). So I might be one of the rare few who would worry about wardrobe distracting there. Am I out of sync with what is acceptable in education settings…? Fellow readers, do you have an idea on faculty attire to share?

    • Very honestly, as a mathematician…. check out the “Prof or Hobo?” quiz.


      OTK boots would distract in the math department, because they are fashionable. That’s all.

  17. Come on! Knee high boots were taboo in the 60’s and early 70’s — then women started wearing them in the office in the late 70’s. Then in the 80’s and 90’s they became taboo again. Now we have many women wearing knee boots again in the office in the 21st century. But wait– OTK boots come back into play in fall 2009 (they have come in and out off fashion since knee boots). First everyone says they’re too risque, now many women are wearing them. I predict in 10 years women will be wearing them regularly to the office, just like knee-highs. And stop with the Pretty Woman comparisons. That is a poor analogy and its a cliche that gets on my nerves.

  18. I saw a lawyer that is a partner in her law firm and she wore black OTK boots with a gray sweater dress at the office and she looked classy. What is the big deal? People need to relax.

  19. Well I guess I am one of the few to have worn my OTK boots to work. I have the 50/50 black leather boots from SW. I wore them with a dress and a semi fitted skirt that falls my knees. I thought I looked fine. As long as the OTK part doesn’t show…

  20. I see nothing wrong with wearing otk boots to the office so long as they are paired with a professional ensemble fitting for your work environment. The fact that many see it as “pretty woman-ish” does not make it inappropriate. I’m curious to know exactly how it violates dress code. Once upon a time and even now, there are some who feel heels over 3″, fishnet tights/stockings, a leopard print of any kind etc., are not work appropriate. Boobs out, short/tight dresses and skirts and tight slacks are inappropriate, NOT six extra inches of leather or suede that cover more of your leg than the “traditional” tall boot. Otk boots are one more fashion choice that may not be liked or popular to all, that does not make them inappropriate. It’s just fashion.