Poll: Are tall boots ever acceptable for a conservative office?

Nine West Women's Iwas BootWe haven’t done a poll on this in a while, so here’s the question of the moment: are tall boots ever acceptable for a conservative office? We’re seeing lots of over-the-knee styles available at surprisingly respectable places like Saks, and obviously engineer boots, cuffed boots, and more are regular weekend wear.  But what about for the office?

To us, this is one of those things that a young woman can’t be too cavalier about — if you want to be taken seriously, avoid clothes that will make some people joke that you’re a “dominatrix.”  After all, if Condoleezza Rice can take flack (from a female reporter, no less) then we would say that these should be strictly off-limits for a conservative office proper.  (If you want to wear them for commuting purposes or with pants, we think, have at it.)  We might also argue that this is perhaps the dividing line between a casual office and a conservative office — in a casual office you can get away with more fashionable, trendy pieces.   But that’s just our $.02, obviously — what are your views, readers?

Pictured: Nine West Women’s Iwas Boot, available at Endless.com in half-sizes 5-11 for $104.47 (were $190).


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  1. I don’t see anything wrong with a tall, leather, knee-high, classic shape, mid-heeled boot paired with a sheath dress and cardigan or pencil skirt and blouse.

    As long as you stay away from cheap looking materials and faux leather, funky embellishments, over-the-knee or slouchy styles, and crazy platforms, I think a well-made tall boot is a very classic and elegant look. The shape of the toe is also key. Anything overly pointed, squared or rounded will either look slutty or cheap. IMO, a slightly rounded point is the way to go.

    I often wear my black Banana Republic pointed toe boots with a 2.5 heel in the winter. I always wear black tights when I am wearing the boots with a skirt or dress. It looks off to me when you see bare kneecaps between a skirt and a dark boot.

    • operaghost :

      Since when are rounded-toes slutty? BTW, my grandmother wears 2.5 inch heels. If its less than three inches, why bother?

      • Defensive much?

      • Wow.

        I was referring to the overly rounded, platform style boots. And I also said slutty OR cheap – boots with a really round toe and a large platform look cheap. The toe of the boot, as well as the material it is made from, determines whether it is law office-acceptable.

        A higher heel on a tall boot is perfectly fine. Mine just happen to be lower heeled, which I find easier to walk in during Chicago winters when no one shovels their walks and there is a layer of ice over all of the sidewalks.

      • why bother with a lower heel? because at 24, my knees are already messed up pretty bad and the last thing I need is more stress on my legs and feet from high heels if I want to avoid much pain and suffering by the time i’m 50.

  2. I think boots with the pointy toe = dominatrix or witchcraft gear. So, the toebox of the boot makes a difference. And if we add a stiletto heel with the pointy toe box, that is asking for flack. If the toebox is more round or angular, I think it looks more acceptable, even with a stiletto heel. Boy, I sound so particular! :) It’s all about the details with me.

    On regular office days, boots to the office seem fine, especially when it’s raining or autumn-y. However, I don’t think they are acceptable if you are going to court or interviews or meeting clients. Thankfully, so far, that answer choice has gotten 0%.

  3. We all work in the Matrix. That’s the whole point of the Matrix.

  4. Anonymous :

    Depends on boot, dress/skirt type and body type/height. I am on the short side, not voluptuous and wear conservative, flat knee-high boots (think Loeffler Randall Matilde) with wrap dresses or other knee length dresses a lot–you really can’t get more conservative than that! But I also think that heeled boots are okay with these types of office dresses. I think most knee high boots are inappropriate with skirts or short dresses, even for interns! And seriously, even if you are of an age group/position that is more forgiving of dress codes (e.g. just out of college law firm staff, and you know who you are, woman who just passed my office wearing the offending outfit), please do not wear tall boots over leggings and a long blouse. We know they are leggings.

  5. Oh, also, I don’t really see what one mocking comment about Rice has to do with anything. Women in power get made fun of about their dress and appearance; it’s the consequence of living in a sexist society that hinges women’s value on their appearance and then sets up a virgin/whore dichotomy (or frump/slut, contextually) where women can’t win. We haven’t stopped wearing pants suits because douchebags mocked Hillary’s. I suspect if Rice had worn plain black pumps that reporter – or another one – would have gone for “matronly” instead.

  6. Fashion Obsessed, Work, Not So Much :

    Depends on boot, dress/skirt type and body type/height. I am on the short side, not voluptuous and wear conservative, flat knee-high boots (think Loeffler Randall Matilde) with wrap dresses or other knee length dresses a lot–you really can’t get more conservative than that! But I also think that heeled boots are okay with these types of office dresses. I think most knee high boots are inappropriate with skirts or short dresses, even for interns! And seriously, even if you are of an age group/position that is more forgiving of dress codes (e.g. just out of college law firm staff, and you know who you are, woman who just passed my office wearing the offending outfit), please do not wear tall boots over leggings and a long blouse. We know they are leggings.

  7. I am an assistant state’s attorney, in a relatively small county. Both myself, and another female assistant (senior to me) wear professional looking heeled boots to court. Part of the reason for this is that we work in a building across the street from the courthouse, so on cold or snowy days, we need to wear them to stay warm/dry while wearing skirt suits to walk across the street.

    I think the key is that the boots are professional looking – fashionable but not trendy, definitely not patent, not chunky, not above the knee, and the heel doesn’t go above 2 or 2 and a half inches. I have a black pair and a brown pair.

    So I do wear them to court, but I wouldn’t wear them to a jury trial, or to a job interview (at least not for a law job).

    It helps that men in my county have a tendency to wear the male equivalent – some sort of snow boot/hiking boot instead of their wingtips when the weather is bad. Everyone knows that it is a necessity, not just an accessory.

  8. Woman of Color :

    So glad you posed this question C. I love boots, however I do experience some hesitancy in regards to wearing them to an office like setting. At the firm I summered at just a few months ago, one of the associates wore a very Autumn type outfit: Brown knee high boots, with a brown jumper that hit right above the knee, and a crisp white shirt. It struck me as being very J-crew and it looked great. There was nothing that screamed Dominatrix (If anything, her outfit screamed I went to boarding school in CT).

    I must admit that I have purchased a pair of over the knee boots (And by over the knee, I mean literally right over the knee, not thigh high). They are grey suede, with a 2 inch heel and non-pointy toe. I have worn them with a navy blue sheath dress that hits right at the top where the boots stop. I have received nothing but complements on the outfit. The outfit was neither sexy, and the boots are not slutty. They gave the outfit an unexpected punch. Granted I am still in law school (hooray for the final year), but I still try to purchase things in an effort to build my wardrobe for life outside of the school library, and I usually *try* and dress professionally for school.

    In summation, I think it depends on your place of work. After I graduate, I will be working at the firm I summered with, and I think the outfit described above would pass. The office is a midsize, business casual in NYC. If I were working for a white-shoe firm, I would definitely leave the boots at home for nights out with the ladies.

  9. I think boots are fine (I’ve even worn them to court–albeit general district court–before). However, I will caveat my response by saying that I think women in boots and skirts at or above the knee with no stockings on underneath look trampy & hookerish. whenever I wear boots, I always wear stockings or tights in a color as close to the color of the boot as possible.

  10. They’re fine so long as they hit below the knee and the heel isn’t too extreme (neither too high nor too stiletto). And wear tights that match the boot color.

    I think they look better with longer skirts – I have a tweed suit with a long skirt that I wear with brown boots and I get tons of compliments. I wouldn’t rock it for an interview but I would for day-to-day office wear.

  11. Knee-high boots okay, over-the-knee boots not okay. No stilettos etc – I agree with EAS and BitterJD above. And ditto on the tights, boots without some sort of tights look very odd to me.

  12. Frustrated academic :

    Long time reader, first time commentor.

    My first job out of law school was for the superior court in Maine and during the winter, it was not practical to wear anything other than boots. I wore my boots, with knee length or longer suit skirts to court and never got any flak. I did notice that attorneys of both sexes would show up in their Bean boots and their suits and no one batted an eyelash.

    Now I work in a major legal market as a staff attorney with the appellate court. In the fall\winter, every woman in the office, from secretaries to attorneys to judges, wears boots with skirts. The boots are always knee length, never more than 3 inches high, and are plain (and the skirts are never more than an inch above the knee). I figure if the judge across the hall compliments my boots, then I am not running afoul of the dress code.

    From a pratical view, boots and skirts are easier in the winter, if I had a dollar for everytime I wore pants, tucked them into my boots, and then discovered salt and other yucky stains on the back when I got to work–well, I might have enough to pay the dry cleaning bill ;-)

    Any suggestiuons for those of us runners\dancers who cannot seem squeeze our calves into the skinny boots that designers seem so enamoured with lately?

    • I’ve had good luck with the Aerosoles line. A number of their boots, like the Sarasota Suede one, have an adjustable second zipper, which is a godsend if you wish to wear them with jeans or pants as well as tights.

    • Ugh…I know just what you mean about the calves. I have the same problem. It’s hard to find boots that stretch that aren’t made of cheap materials!

      • I had such a hard time finding boots that fit! I found the piperlime and Nordtrom’s websites were really helpful – they usually include the shaft circumference in the description and can keep you from having your heart set on something that just isn’t going to work. I bought mine last year but there were a few Frye styles that worked for me, you may want to try that label. I can tell you that Tory Burch and Chloe boots were way too skinny in the calf.

    • divaliscious11 :

      Duo boots from London. they make custom size for larger calves

      diva – former 3 sport athlete with big calves!

      • Oooh ooh! I absolutely agree about Duo.com They are from the UK, so you’ll have to pay shipping but they sell boots by the calf size in all kinds of styles. I bought my boots from Duo and can attest that they are high quality and beautiful.

        I think they are appropriate in cold climates or places with weather, as long as the skirt is sufficiently long. At the shortest the skirt should be no higher than 1 inch above the knee. A short skirt is what makes it look “slutty” in my opinion. I’m also a fan of tights, but I’ve been known to wear them without the tights. My favorite look is a skirt in an A line with a hem right at or just below the boot top.

      • Try Cole Haan. They make boots for a variety of calf sizes.

    • I’ve been pondering the same thing — I have huge calf muscles. The only place I knew of was J.Crew. Thanks for asking, because these comments have been enlightening for me, too.

    • What city is this in? Judges wear the boots as well? Lawyers wear the boots to court? Are their more suits or dresses? Are the tops turtlenecks or blouses? I’m just trying to picture this scenario. Thanks.

  13. Frustrated Academic, Zappos has a nice selection of wide calf boots.

  14. Boots that are knee-high, solid or dark colored, not shiny, and have a low-to-medium or wedge heel are fine. Boots that are over the knee, patent leather or pleather, have fringe or sequins, or have very high, spiky/stiletto or chunky heels are not acceptable. I’d wear tights that match the boots, not sheer nylons, and I’d wear a knee-length or longer skirt.

  15. I think it depends. Also, I agree with almost everyone above — knee-high or shorter, no weird patterns/colors, no stilletos, no super pointy toes, and tights are a must. As a law clerk last fall, I wore a pretty brown tweed dress with cream tights and brown boots that fit the above description a few times and got tons of compliments from the lawyers. I can’t wait to start wearing that outfit again now that it’s getting cooler!

  16. J. Crew usually has wide-calf boots in it’s fall/winter collection.

  17. I regularly wear knee-high boots (suede or nice leather) with skirts that come to just above the knee. Especially in the winter for the reasons mentioned by frustrated academic–in fact I don’t wear pants more than once a week in the winter for exactly this reason and will probably do so even less often this year. That said, I am at a firm in Seattle where things are more casual. If I was still at a white-shoe firm in New York, I wouldn’t think of doing it.

    As for dealing with calves, you can take the boots to a cobbler who will cut a slit in the leather and insert elastic to give it a little stretch. As long as your calves aren’t that much larger than the boots, it won’t be enough for anyone notice. Personally, though, I just don’t buy slip on boots. In addition to having problems with them being tight on my calves, I find it to be very awkward trying to get my foot to go in straight. I only wear zip-up boots, but know about the cobbler option from friends.

    • Good to know re the cobbler option! As for zip-up v pull-on, it doesn’t really matter. If your calves are too big, they are too big.

  18. I have a pair of knee high black boots, not too different from the ones pictured. I also bought a pair of grey suede knee high
    (Cole Haan) at Nordstrom.

    My wardrobe consultant lady let me keep the black ones (to wear with a black and white plaid-ish conservative skirt) and had me return the grey boots. She said the buckle and color didn’t match my work clothes but the black ones were conservative enough.

  19. I agree with most of the above — I wear knee-high boots with a small-ish heel all the time. It’s a great way to keep from having pants that drag in the salt or rain, and I find them very comfortable.

    But I also feel much more comfortable wearing them with tights. I think that weird band of skin between the top of the boot and the bottom of the skirt (especially if you’re pale like me) looks somewhat unprofessional.

  20. Living in Southern Florida, unfortunately, we rarely wear boots. I have a pair I love and, if I lived anywhere else, would be perfect:


    They come in Black and Brown and are currently on sale for $99.

  21. I have a pair of beautiful cole haan boots I got last year that I adore and don’t hesitate to wear to work. They have a 3 inch tapered stacked heel and a pointed/rounded toe. They were expensive, ~350, but will last forever. For those looking for wide calf boots, cole haan has a number of styles that have stretch leather shafts. Not the cheap pleather stretch material, it some kind of specially treated leather. Its great.

  22. For those with awkwardly-sized calves who don’t mind mail-ordering shoes, http://www.duoboots.com/ is an excellent option. You can order by calf size, and there are definitely some options that are suitable for work. (Er, probably not the turquoise suede pair!) I’ve tried a few pairs on in person, and they were very comfortable. Just not in my budget at the time, alas.

    I’m with the majority here – knee-high boots are fine, as long as they’re not too pointy, square or slouchy, and the heel’s not a ridiculous stiletto. And definitely with tights. I personally like slightly louder colours with black/dark brown boots and a plain outfit, but my workplace isn’t that formal. Though my friend who’s an accountant and in suits every day does the same thing…neither of us are in the US, however.

    • divaliscious11 :

      Ah, didn’t see that you’d posted about DUO…I love them…have several pair… and plan on getting a couple more this season…

  23. I seem to have the opposite problem of some of the posters here – I’ve never been able to find an attractive boot that are small enough for my calves (I must be kind of wimpy!). I feel like there’s way too much of a gap between the boot and my leg. Any suggestions for brands that won’t break the bank and will be smaller in the calf area?

    • Designer boots tend to be more fitted in my experience, as do ones that are more fashionable and less athletic. I can’t say enough good things about Loeffler Randall boots. The calf is just the right width, the leather is amazing, and the boots are gorgeous.

    • divaliscious11 :

      duo also does narrow as well…

    • Anyone know boots that work for a smaller calf on a shorter leg? I think my problem is that the widest part of my calf falls below the widest part of the boot and it just looks awkward. There’s extra fabric around the ankle where the boot gets pushed down, and the gap at the top where my calf is too small. When I lived in Japan, I found that boots came in different heights and calf widths, but I haven’t found anything similar here in the US.

  24. I live on knee-high boots in the winter, I wear them every day with pants and skirts! I have about six pairs of them, brown, reddish/brown, black–with variety of heel heights. It’s freaking cold in Iowa, if anything I wear them because I need the warmth of the leather! I don’t buy the crazy pointy with “unusual” accessories on them, just regular–plain boots, some with an inch-heel.

  25. Anne Vohl :

    There is an office and court look with boots and a slightly flared and slightly longer skirt that works well for a suit or for a skirt and top. The boots come to above the bottom of the skirt when you are standing. The look is somewhat based on a middle-European 19th century peasant costume – think “Bartered Bride” – and is very pretty and feminine. It’s kind of nice to match a belt to the boots.

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