Boots at the Office: THE POLL

Can you wear knee-high boots to the office with a skirt? Reader B wonders…

I live in DC and work in the public interest world.  I love wearing boots in the winter and when there is inclement weather.  I have two very nice pairs, one which is ankle-length and has a nice looping strap and buckle and the other that is nearly knee-high and has a four inch heel and some great detailing.  They are both fairly formal looking.  Is it appropriate to wear these types of boots to work?  Would it ever be appropriate to wear the tall ones with a knee-length or slightly shorter skirt or dress (as opposed to wearing work slacks over them), and in that instance would tights or leggings be appropriate?

Regarding the ankle length boots, I’m going to say that while I’ve heard from some readers who think all ankle- and mid-calf-length boots are hideous (I love ’em, so I’m not in that group), I’ve never heard anyone say they’re inappropriate for the office.  Wear ’em with pants all you want; I’ve even seem some women successfully pull them off with skirts and opaque tights that matched their boots exactly.

Regarding the knee-length boots, now… that’s a more interesting question.  It was only a few years ago that the fashion writer for The Washington Post reacted with horror to an outfit Condoleezza Rice wore that involved black knee-high boots, ultimately calling her a dominatrix.  As she wrote:

As Rice walked out to greet the troops, the coat blew open in a rather swashbuckling way to reveal the top of a pair of knee-high boots. The boots had a high, slender heel that is not particularly practical. But it is a popular silhouette because it tends to elongate and flatter the leg. In short, the boots are sexy.

Rice boldly eschewed the typical fare chosen by powerful American women on the world stage. She was not wearing a bland suit with a loose-fitting skirt and short boxy jacket with a pair of sensible pumps. She did not cloak her power in photogenic hues, a feminine brooch and a non-threatening aesthetic. Rice looked as though she was prepared to talk tough, knock heads and do a freeze-frame “Matrix” jump kick if necessary. Who wouldn’t give her ensemble a double take — all the while hoping not to rub her the wrong way?

It’s a great article by Robin Givhan and one that has to be read.  To be honest, when I first read it — way back when in 2005 — it seemed a bit much.  My personal delineation line for the “too sexy” boot had always been the knee:  if it hit under the knee you were stylish; if it hit over the knee then hey, at least you had a place to store stuff while you worked the streets waiting for Richard Gere.  But not everyone is on the same page with that delineation.  For example, I remember having a discussion back in law school with a friend of mine (with a tongue ring, mind you!) who asked me if I thought knee-high boots were hooker boots and unacceptable for the office.

Maybe these reactions alone are enough for any professional woman to say, “You know, why chance it at the office?”  In fact, that’s still my advice: wear your knee-high boots all you want outside the office, but really think twice before wearing them in the office.  Even though these two conversations were a few years ago, there are plenty of people who form an opinion on what is and is not appropriate for the office when they start working — so unless your boss has been working for less than 7 years, there’s a significant chance he or she might think tall boots are inappropriate for the office.

But perhaps knee-high boots have come a long way since then. So here’s the question:

I’m curious, readers — what are your thoughts about knee-high boots at the office?


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  1. We all agreed? That’s got to be a first.

  2. I’m kind of surprised the poll doesn’t qualify anything about the heel height. I think a flat/riding boot style rarely looks too Julia Roberts-esque.

    • True – although flat boots can also veer too casual for the office, even if technically conservative enough. I have a coworker who sometimes wears flat suede boots with a rubbery-looking sole and some type of buckle that jingles when she walks, tic tac style – they look more designed for an afternoon at the pumpkin patch.

      • I think flats are too casual. I can’t figure out how to pull them off without looking like its Saturday.

        • Anonylawyer :

          I agree – I save my flat riding boots for Fridays (our casual day). My typical boots have a 3″ heel. I have 3 pairs of heeled boots in regular rotation plus 2 pairs of riding boots, but typically only the heeled boots get worn in the office.

  3. I wear black knee high boots with a shorter (3″) stacked heel. I only wear them with black tights and I usually only wear them when there’s snow on the ground. (don’t have enough of a commute to deal with the hassle of changing from snow boots to shoes, but cannot abide by snow/slush in my shoes.

  4. I would be lost without my boots, which I wear nearly every day in the fall/winter to my business casual to casual office.

    I can’t see the poll — in case anyone else is having the same problem, here’s a direct link.

    • Diana Barry :

      Aha. I couldn’t see it either.

      I wear knee-high boots all the time in the winter, but they are riding boot style, so low/flat heel. I think the high-heeled boots are more questionable and a know-your-office kind of thing.

      • I probably should have mentioned that all of my boots are flat or very low-heeled — more for comfort than because of any particular sense of office appropriateness. :-)

      • a passion for fashion :

        i always find this interesting, how people can disagree so much about stuff like this (myself included), which is why my usual rule on anything clothes related is wear what i feel comfortable wearing and looks put together. but i digress . . .

        my point was that to me, i consider low/flat heeled boots too causual for the office and the only way i wear knee high boots (which I do, from November through March, and never after) is with a heel (2-4 inches)

  5. I wear black knee-high boots and dresses to work almost every day. (I’m a gov’t attorney)

    • Government attorney, black boots with no heel, dress, and black tights. They are more stylish than riding boots. I don’t feel strange as long as I’m wearing a sheath dress or suiting. To me it looks no more stupid than textured tights and heeled Mary Janes, which I see a lot.

    • great atty

  6. When I was at my semi-conservative law firm, I wouldn’t have worn boots at all. At my public interest organization, anything that doesn’t scream stripper works.

    • anonymous :

      I would make pretty much the same assessment. I think conservative tall, low-heeled boots with a long skirt could work at a conservative firm on a cold day, especially if you were staying in the office.

  7. I’m with some others above–riding boots/lower heeled boots aren’t so bad. But if we are talking 4″ stiletto heels, it can start to verge on too sexy. But heel isn’t everything–I have a black motorcycle-esque pair with a low chunky heel that are knee high. Love them for going out and feeling kick-a$$, but wouldn’t wear to the office.

  8. The combination of a four inch heel and knee height boots would make me say no way. I think that flat heel tall boots can work in a more casual environment with a knee length preppy skirt/ dress look and in more formal setting the black boots like C Rice is wearing with a lower heel. But sorry Reader B, unless at least two other women you respect are wearing those kinds of shoes, you are out of luck.

  9. Anonymous :

    I am wearing black suede 3.5″ heel Cole Haan boots today. Seems like such an appropriate post.

    I also think it depends on what you pair them with. Borderline too short black skirt? May want to rethink. Slightly below the knee tweed skirt and turtleneck? I think you are definitely work appropriate for a business casual office.

    • I am almost certainly wearing those same boots today with a tweed skirt, sheer black hose, and a cashmere sweater. I first got these boots in black but loved them so much, I bought the same ones in brown. They are definitely one of my work staples in the fall/winter.

    • I agree, although my knee-high boots rarely have a heel higher than 2.5. Worn with a knee-length skirt, especially with tights or black opaques, they are fine with a conservative jacket or top. Especially with the rain in the PNW, I live in boots in the winter. Short under pants, knee-high with skirts. Hate rain in my shoes.

  10. Knee-high boots are very popular at my government office, with or without tights. I’ve seen everything from riding boots to ultra high heels with platforms and no one seems to care one way or another.

  11. phillygirlruns :

    i had trouble finding a good pair of office-appropriate knee-high boots, but finally did (the cole haan air violet style we discussed a week or so back, with goring done by way of vertical leather ruching on the sides). the heel is about 3-3.5″, and i wear them with pencil skirts or sheath dresses and dark (not just black) tights. i used them to ease myself into textured tights in the office.

    last year i bought a pair of what are, in retrospect, kind of awful flat boots. i was sucked in by the fact that they fit my calves, which is rare. they’re light gray and have three straps with buckles up the calf. i look like peter pan if i wear them with pants, they’re too casual to wear with skirts to the office, and they’re too light to wear with most of my casual dresses. stupid, stupid impulse buy.

  12. After actually reading the entire Washington Post article about Condoleezza Rice, I have to disagree with Kat that the author “reacted with horror” at Rice’s outfit. On the contrary, she discussed at length how it was a much more powerful outfit (bold, authoritative, conveying toughness and focus) than other female leaders’ typical sartorial choices (bland, photogenic hues, loose-fitting, sensible). The “Dominatrix” quip in this article has always been taken out of context. The author’s point is that we’re still uncomfortable with powerful women; that power, in women, is always linked with sex. “When looking at the image of Rice in Wiesbaden, the mind searches for ways to put it all into context. It turns to fiction, to caricature. To shadowy daydreams. Dominatrix! It is as though sex and power can only co-exist in a fantasy. When a woman combines them in the real world, stubborn stereotypes have her power devolving into a form that is purely sexual. Rice challenges expectations and assumptions…. If there is any symbolism to be gleaned from Rice’s stark garments, it is that she is tough and focused enough for whatever task is at hand.”

    On the question at hand, I work in a mid-sized law firm in New York, and it’s quite common among the women here to wear pencil skirts and knee-high heeled boots, usually with dark tights. When the weather turns warm, the tights disappear and the boots are shifted out for high heeled pumps. I’m not sure if either boots or heels have made it to Biglaw yet, and we are a business casual firm, but I think the boots and skirt look is a winner (not to mention practical in our climate).

    • Robin Givhan’s the only fashion writer to win a Pulitzer, iirc!

    • FWIW, I always thought that Dr. Rice, with that look, looked a lot better and more professional than the standard “female politician” look of colored suit, helmet hair, and oversized pearls (Nancy Pelosi and Hillary Clinton spring to mind). Much more powerful, IMO.

      • So from your comment … only Republican women know how to dress?

        • Putting politics aside … I can’t think of any other female politicians, Republican or Democrat, who “got it” fashion-wise the way Rice did. (And for what it’s worth, I’m at the opposite end of the political spectrum from Condoleezza Rice.)

        • They were just the first 2 that popped into my head, jeeze. If it makes you feel better, Kristin Gillabrand (I’m spelling that phonetically) always seems to look great, and Michelle Bachmann swings wildly from looking great to terrible.

          I suspect it’s more of a generational thing than anything. Seems like the really prominant Dem women are more in the Clinton to Pelosi age range (60+, came of age more in the 80’s), while the current prominant Rep women are more in the Palin to Rice age range (40-60, give or take because I’m not actually sure how old they are, but more in touch with modern looks). I can’t really think of a good example of a really prominant older Republican female politician (Elizabeth Dole? I can’t even think of how she dresses. Margaret Thatcher?) or a really prominant younger female Dem, other than KG, and maybe Gabbie Giffords, but I’ve only really seen her since the shooting, off the top of my head. (I’m not counting first ladies/political wives as politicians here.)

    • Seattleite :

      I was composing your first paragraph in my head, so thanks for saying that. Also, Ms. Rice is quite fit and has great legs, so probably anything but *deliberately dowdy* would have drawn comments. Given that she was SecState at the time, she’d earned the right to wear the Rice-version of red-power-suit.

      I also happen to think she chose that look deliberately, knowing that pictures would be seen in the Middle East.

    • I must admit that Rice’s outfit in that photo has always been a source of fashion inspiration to me. I’m about as far from her politically as it’s possible to get, but I think she looks stunning (and for what it’s worth, no one in my firm would blink at those boots).

    • I agree exactly. I am in a mid-size midwest firm, with a relaxed business-formal vibe (suits and separates). Tasteful knee-high boots with a mid-heel (2.5-3.5 inches) and a knee-length skirt are totally common. It would never even occur to me that they were overly sexy for the office.

  13. Anonymous :

    I will wear my knee-high 3″ heel boots with a knee length skirt if I am not in Court and have no clients to meet. Regardless, I was at a docket call at state Court today and 1 attorney was wearing black knee-high 3″ heel boots with a knee length skirt.

    • I fess to wearing knee-high boots with a skirt suit to motion call at the Daley Center yesterday. With the disgusting Chicago weather I wanted the leg coverage; my coat isn’t full-length. I still think I looked more professional than 3/4 of the other attorneys of both sexes, as is usually the case in that courthouse, which I swear based on other attorneys’ attire must contain a secret nightclub or a portal from the late 1970’s (I’m looking at you, men who think suits never goes out of style).

      • oh I’m so glad. I take the red line to the Daley Center at least one day a week and in the winter I’m always stumped about what to wear – there’s no good place to stash winter boots/gear when I’ve got a couple different cases to cover. I finally decided it was just going to have to be boots because I wasn’t going to wade through slush in heels and nylons.

      • I was in domestic relations court in the fall and one of the attorneys was wearing- I kid you not- approx. 4 inch super strappy stiletto heeled sandals that were completely encrusted with rhinestones. At 9 am. I was astonished.

        Also, I was the only female (of many) in the room who was wearing a suit. Maybe Corporette hasn’t quite caught on here in Chicago?

        • *domestic relations court at the Daley Center

        • Local court anywhere is just a motley crew. In Boston, I saw boxy oversized jackets with what appeared to be fleece pants and moon boots. In San Francisco, I saw floral blouses with khaki pants and sandals. In New York, I saw a black and white sundress (client was in a jacket and slacks, amusingly). It makes me obsess less, to be honest. I kind of appreciate it.

          • It’s interesting to note the difference in the level of dress between state/local courts and federal court. The bigger firms tend to dominate in the federal courts, so the dress is both more conservative and more expensive. In local courts, I’ve seen women attorneys wear sweater sets with slacks. For me, it depends on the judge I’m appearing before, and then the choice is only between pant suits and skirted suits. If the judge is an older male (read, “old school”), I’ll wear a skirted suit and pumps.

          • I swear to god, in a local MA court I saw someone trying to pull off yoga pants as suit pants…. it looked pretty awful.

  14. lefty lawyer :

    In my opinion, if they are worn with a below-knee skirt that covers top of boot, no problem. I have a problem with above-knee skirts with boots. I’m a pretty conservative dresser and I’m a “boss”. Kat is right that opinions on appropriate office dress are formed when you start working and mine date to the “Dress for Success” era. “Boot length” bias cut skirts were common in the 80’s, and I still love them.

  15. I’ll go on a limb and say that boots can be appropriate for a job interview. For my last two interviews, I’ve worn just-below-the-knee boots. They’re very plain, with a stacked heel, no buckle detailing, in a very dark brown. For one interview, I wore a plain gray wool skirt suit, carried a sleek tote, and needed the boots because it was raining. If I’d worn a pantsuit, I might have gotten the trousers muddy. If I’d worn pumps, I might have gotten mud or dirty street water on my lower legs. But a knee-length black rain jacket (trench style, not windbreaker style) plus boots were just the ticket. For the other interview, there was snowy glop on the ground, and it’s not as if I could wear snow boots to the office and ask to change in the ladies’ room before speaking to the interviewer.

    Didn’t get the jobs, but I’d be astounded if my boots were the reason, or even one of the reasons. At one of these interviews, there were 100+ applicants for the job and 14 interviewees for 2 positions — it was an economy thing, not an attire thing. Neither office was super-conservative biglaw.

    • I agree. No reason to show up with soaking feet and risk slipping and falling in pumps.

    • Anne Shirley :

      I have never had a problem asking the receptionist for the bathroom before she buzzes the interviewer, and have often left snow boots in a bag at the front desk. It may work for you, but I wouldn’t recommend boots for an interview.

  16. As long as the boots aren’t white or cream, go for it.

  17. I’m a DC nonprofit attorney too. As long as the boots are of a heel height, fabric and color that would be appropriate for pumps, they’re perfectly acceptable to wear to the office. I wear riding boots all the time.

    But leave the pink, patent leather, clear-5″-heeled boots at home.

    • I am intrigued. Where in DC does one see and/or acquire pink patent boots with 5-inch clear heels?

      • Lawyer Bird :

        There’s a club down the block from my apartment where I bet you can see a pair or two…

    • This. I disagree with the comments saying only flat boots are appropriate, or saying any heel is too much. I think the idea is that a boot that essentially looks like a conservative pump, except adding a shaft, is work appropriate. And I would add that the shaft is straight up and down (no slouching or gathers) and little to no hardware/decoration (multiple buckles make it look more casual to me).

  18. I work in a public accounting firm and I frequently wear pencil skirts with my black suede La Canadienne boots. They are almost knee-high and I typically wear them with black opaque tights. I’ve gotten many compliments on them from managers and partners, and they often wear similar styles. Then again, I do work in a firm with mostly women, and many of them are pretty fashion-forward.

    • Public accounting here, and I have never seen anyone wearing boots unless its with jeans on a casual day. When I worked in an IB, women were generally more formally dressed (still suits most days) but the culture was different and a lot of women would wear boots with a dress.

      • I’m a senior partner in a mid-sized public accounting firm, and I often wear black suede boots with knee-length pencil skirts and black tights. As long as the boots are dressy and conservative (no sky-high heels or animal skin patterns), I think they’re more appropriate than pumps with bare legs.

  19. I honestly think it depends on the office so I’d get a feel for what other women are wearing. But I have no problem wearing them to work. I currently work for a non-profit member association in DC and wear my below-the-knee boots with 3 inch heel on a regular basis (with tights) during the fall/winter/spring with a knee-length skirt. When I worked for a Member of Congress, I also wore my boots (albeit only after another woman in my office who had a higher position than I did wore hers). Granted, wouldn’t wear them with a mini-skirt to work (but then wouldn’t be wearing a mini-skirt to work in the first place). But an above-the-knee or even a below-the-knee skirt/dress is entirely appropriate.

  20. MissJackson :

    I wear boots at least 50% of the time in the fall and winter with tights. Most if not all of the female associates do too, and at least some of the female partners.

    In addition to heel height and general style, the fabric matters. Condi’s boots seem to be especially shiny, and that (in my mind) makes them seem less appropriate. My black leather boots aren’t matte, but neither do they shine.

  21. This thread reminded me that we have a paralegal who sometimes wears red patent stilleto above the knee boots to work. I don’t think she could get more unprofessional.

  22. Business, Not Law :

    Below the knee, fine…lots of people wear them here at varying heels heights. However, knee high with a wedge…that is bordering on costume-y IMO and reminds me of something that Gene Simmons would be wearing. But in full disclosure, I am not a fan of wedge-boots at ALL.

    • Always a NYer :

      A woman in my office was wearing knee-high wedge boots today. Did I mention they had buckles going up them?

      • Business, Not Law :


        • I am in NY and see TONS of knee-high boots with a wedge heel these days. The ones I see have looked really delicate and dressy. Not at all like KISS.

  23. When I was a law clerk (state trial court, mid-south, 2 years ago), in the winter, basically every female attorney would be wearing black knee-high boots, usually with black tights for the younger sets (under 40-ish) and hose for the older ones. It was literally half or more of the female portion of the crowd on most motion call days November to March.

  24. DC Professional :

    I work in a business casual office (jeans are not allowed) at an association and while our boss wears suits each day, it is not a requirement for the rest of us. I have found that simple, classic riding style boots in the fall and winter are the best bet, and with dark tights can look very professional.

  25. MeliaraofTlanth :

    I wear them all the time in my business-casual office. Though if I’m wearing them with a skirt instead of pants, I feel like it requires opaque tights. I tried my just-below-knee black boots (very proper looking) with a just-above-knee dress and no tights one time and my boyfriend said “Counselor!” in a tone that made it clear I needed to add the tights for office wear. General rule: if boyfriend notices, too sexy for office. If he doesn’t, it’s fine. He doesn’t notice with tights.

    And yea, I’ve see a lot of knee high boots on female attorneys in court this winter. But always with tights.

    • Agree. I don’t like the look of knee-high boots with bare skin or nude hose.

    • Business, Not Law :

      Agreed…if I ever get the “you look hot” comment before leaving the house, I immediately change my outfit!

      And this isn’t to say that I am leaving the house in too-short skirts or cleavage baring tops (I am VERY conscious of both) but that some combinations of skirts/tops/shoes are apparently more visually-evoking than others.

      • ha. This morning I got an outfit comment from husband, but it was that I looked like I was part of a very conservative religious sect. I’m not.

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