Corporette.com

83 Comments · by

Riding Boots … to the Office?

Business Casual· Fashion Gaffes· Shoes | · ·

Frye - Dorado Riding (Bordeaux Textured Full Grain) - Footwear

Reader J wonders:

I have a question I’d love to see addressed on your blog (or maybe you can just give me your $.02): can I wear riding boots to work? If so, how? I am in court every day, but it’s juvie so it’s not like I have to wear a suit every day.

Hmmn. Well. Honestly? My $.02 here is that no, you really should not wear riding boots to court. Certainly not with leggings or skinny pants, and definitely not with miniskirts. The “librarian in the 80s” look of a knee- or calf-length A-line skirt, fitted jacket, and riding boots might work… but something tells me that’s not what you have in mind. You can, of course, wear them beneath trousers.

This post contains affiliate links and Corporette® may earn commissions for purchases made through links in this post. For more details see here. Thank you so much for your support!

(Pictured above: Frye – Dorado Riding (Bordeaux Textured Full Grain) – Footwear, $458 at Zappos.)

I guess my gut reaction is stemming from the fact that these boots are originally intended for riding horses. Like pants intended for yoga, and leather jackets intended for motorcycle wearers, they may occasionally be acceptable for a very, very casual day at some offices — but court is not one of those places.

I’ll let the commenters weigh in here… ladies? When can and can’t you wear riding boots to the office? Am I wrong to group all “intended for” clothing into one bucket?

Hunting for black knee-high boots? Here are some of our long-standing favorites as of 2023!

Above: one / two / three / four

About Kat

Kat Griffin is the founder, publisher, and editor-in-chief of Corporette. You can read more about her here.

Comments

  1. stc

    I spent my 1L summer working for the AG’s office that represented social and health services, so I spent a lot of time in juvie. Frankly if you had something that looked like a jacket, you were fine. Boots would have been fine.

  2. K

    I will wear riding boots to the office on casual Fridays only. I will wear skinny jeans or “jeggings” (gasp) tucked into them, and then usually a looser sweater or top. My office gets pretty casual on Fridays though. I would never wear them into the office any other day of the week.

    • lawyerette

      ooh those are lovely! they’re on sale at 6pm (in brown only unfortunately)

  4. Divaliscious11

    Wear to my business casual office with knee-length skirt and tights…. Probably wouldn’t wear to court, but i don’t go to court so….

  5. M

    I’m a bit confused by the article. It’s okay to wear them under trousers, or it’s only okay to wear them on casual days?

    And if it’s not okay to wear them as normal office wear – is there a type of boot that is?

  6. v

    Seems fine to me – I don’t know why the post assumes the questioner would wear them with leggings or a mini-skirt; nothing in the letter suggests that to me.

  7. A

    Can I ask a related question? There’s been talk in the comments before about whether boots are ever appropriate in a more formal office. I work in a small office where dress is a few notches below business formal (I wear a suit 2-3 times a week and a jacket/skirt combo the other days; no jacket on Fridays) and would love to be able to wear boots on reaaallly cold days when my ankles just freeze if I don’t have socks on. Would a pair of low-heeled boots be appropriate? I’m thinking something along the lines of these (but hopefully a cheaper version): http://www.zappos.com/cole-haan-justine-air-tall-boot-55-black

    FWIW, I’m the only female lawyer in the group, so I don’t have much in the way of comparison. Thank you in advance for any advice/suggestions!

  8. Becky S.

    I wear boots with a mini and tights to court. Haven’t been thrown in jail yet.:) Depends on the court, I guess.

      • Anonny

        I didn’t mean that to be snarky, i just know from experience that it gets talked about…a lot…for months. We had opposing counsel who did that and that’s all anyone talked about. I’m sure the judge noticed, too.

        • L

          Unfortunately, Judges talk too. I worked on a federal appeals court and they talked when people wore “memorable” outfits.

        • anon now

          Something similar happened when I observed adult court years ago. She looked early 40s agewise, in knee-high heeled black boots, leather skirt, and leopard jacket. I honestly thought she was a defendant’s girlfriend until her client’s case was called and she started doing her thing. Later I mentioned her to the attorney I was shadowing and he shrugged dismissively. This was not an attorney anybody was going to be doing any favors for.

          • Becky S.

            Well, the skirt’s knee length which I guess is a mini for me, and the sweater/jacket was conservative. It’s pretty in line with what the other female attorneys wear in misdemeanor court. And I have more work than I can handle.:)

    • EN

      My mother has these boots (got them way on sale at midwestern department store Von Maur) and I can confirm that they are both gorgeous and comfortable in real life. I’m quite jealous.

  10. chix pix

    Never – because what it looks like to me is someone is saying, “I am a horsewoman”. That’s like saying – I have a little more money – or something – than you do.

      • equestrienne

        What’s wrong with saying “I am a horsewoman” ?? Seriously, ALL hobbies require money. Even a shitton of money, like riding does. It’s not like running is cheap ($100+ for a pair of shoes, to be replaced every few months, expensive “running” clothes…) and that’s a relatively “cheap” hobby.

        I could object to riding boots, definitely. They’re pretty casual. But because they imply that you have money? Or say that you’re a horsewoman (which, honestly, who believes that everyone wearing riding boots these days is a horsewoman? Everyone at my barn wears ankle boots and halfchaps anyways)? Nope, not actual reasons.

    • spacegeek

      LOL I own 4 horses. And I wear short “paddock” boots when I ride because they are more versatile (and I don’t show). I wear what are called “half chaps” over the boots to provide the comfort needed while riding, but I take the chaps off afterwards for cleaning and mucking.

      FWIW, fashion riding boots are totally different than “real” riding boots because riding boots never have a zipper on the inside. That would pinch the rider and the horse!

  11. ERP

    It is not appropriate to wear riding boots to court (even Juvie) IMO. I look twice at a lawyer who thought that was an appropriate look. Save it for after work and weekends. Social workers are another story and held to a different standard. As officers of the court, we have a duty to respect each other, and the judge by dressing appropriately.

  12. kng

    i would never do this, ive even felt uncomfortable doing the high boots with skirt/dress look at work – but i’ve seen this done very well on other women, generally with a darker suit, dark tights, and dark brown boots – i think it shows a lot of personality like the look, but it’s not for me.

  13. JAS

    Mostly Off -topic, but thought I would share for fellow navy skirt weareres….this is just a little PSA… I have very dark navy pencil skirt that I struggled to find appropriate tights for (sheer hose are too formal and not warm enough for my office). I also feel burgandy, plum, or cream would be too loud/too much contrast, I don’t have the right shoes for brown, and black doesn’t look right. I also didn’t like any of the gray tights I looked at because they were too light or heathered and looked funny with black shoes. I had resigned myself to only wearing this skirt with tall boots (which I was also unsure of) or not at all in winter.

    But! At TJ Maxx the other night I found the perfect shade of gray tights. They are a dark smoky semi-sheer gray with criss-cross pattern, and they have the slightest plum/blue hue so they look wonderful next to navy! I am so happy with them. They are Chinese Laundry brand, unfortunately no color name on the package, but came in a pack of 2 (one solid, one patterened, both same color).

    The best part is, i wasn’t even looking for tights; I was just waiting in line and someone had left these in a random place by the register.

  14. surrounded by lawyers

    Kat asked about the “intended for” premise in office clothes. I think it depends how far back you’re going to go in the “intentions” behind certain articles. Really, many of the clothes we now wear to look professional–blazers, button-up shirts, trousers–were originally “intended for” men. They’ve been adapted, and maybe riding boots can be too?

    • NYC

      Yeah, I was thinking the same thing, in particular with military inspired jackets.

  15. KJ

    I was always under the impression that a polished set of riding-style boots was the classy boot to pair with skirts. They tend to be low-heel and lack any overtone of objectification you find with higher-heel boots (sort of like the difference between stilettos and flats).

    Of course most of this is hugely influenced by the fact I had an awesome physics professor in college who always wore skirt suits and knee-length boots and looked amazing. Court may be different but I don’t see how they could be unprofessional if done well in the office. Certainly finance stole them a long time ago.

    • SS

      Yeah I agree – riding boots = classy boots. I think it helps that they are usually brown… for some reason brown boots look more classy in general?

  16. AIMS

    I had an internship in juvie court while in law school, and can attest to the “anything goes” wardrobe of some of the lawyers there.

    • Anon

      That’s good to hear, because a friend of mine will be working in juvie court after law school and she dresses kinda like your elementary school art teacher, complete with “ethnic” jewelry. I was wondering how she was going to make a being in court every day work…

  17. CJD 801

    A colleague and I noticed this at an investigator’s meeting (I run clinical trials for cardiac devices) a little over a month ago. I thought that the girl looked trendy, but silly. Not overdressed, not underdressed, just silly and young. I understand that my profession may be a bit different than some of the readers here, but when dealing with patients I have found it important to be perceived as more mature (I actually learned this from a younger colleague). And while if I were working in a different type of research with younger patients (as I have in the past) I might wear that young woman’s outfit, I would not wear it around elderly patients. The girl looked extraordinarily young, and the riding boots and skinny jeans only seemed to add to that so much so that I thought she was no more than 18.

    Also, when working with juveniles in court, I find it more important to look professional and authoritative. You play several roles for them when you are in the court with them, and you should look as though you can be their professional mentor, not their personal one. Just an opinion.

  18. Midori

    Huh. Coincidentally, I’m wearing riding boots to the office for the first time this season today. But my office is fabulously casual–jeans and sweater are fine for no-contact-with-the-public days. Blizzard yesterday + highs in the low teens + perfect day to break out the boots.

    Unrelated: Can I wear a navy/white herringbone pencil skirt with navy tights? Is that weird?

    • K

      I think it would be fine – I wear black tights with my black and white herringbone pencil skirt all the time, don’t think it would be any different with a navy combo.

  19. cbackson

    I wear riding boots to my (business casual) office all the time. I wouldn’t wear them to court, but I wouldn’t think twice about wearing them to the office.

  20. mamabear

    I’m in the office today in a black turtleneck sweater, knee-length black denim skirt, black tights and brown riding boots. The brown breaks up the blackness of the outfit, and the rest of it being black makes it a little dressier. As a result, I think I look reasonably “business casual.” If that’s an OK level of dressiness for “juvie” court, I’d say go for it.

  21. Mountain girl

    I wear riding boots to the office all the time. I have black, gray and brown and wore one of them with pants and a jacket almost every day last winter. I am in health care finance and in Colorado we probably have a much more casual style than others but I love my riding boots. I like that they are low heeled and practical for slick wet days. I especially love them with herringbone or tweed dress pants.

  22. b23

    This makes me think of a friend of mine in college who, when told to dress “business casual” for an interview for a student organization, wore a full suit up top and boxer shorts and slippers on the bottom (doubled up so no slip ups). The top was business; the bottom was casual. It was hilarious–unfortunately, those days are behind me.

    • 2L NYC

      I wonder if this is a common thing to do — I had friends who did this in college as well, for interviews and occasionally for formals (much to the chagrin of their dates, but the amusement of everyone else)

  23. Lizbet

    Somewhat related question: I have low-heeled black boots (not riding boots) that are perfectly appropriate for my corporate office. However, I feel they’d look funny with my pencil skirts. Do longer skirts look frumpy these days? (I’m thinking of Kat’s “Librarian in the 80s” reference — very funny!)

  24. Lawgirl

    I haven’t been to juvvie court before, so can’t weigh in on the appropriateness factor. Big Firm Lawyers representing “Corporate America” undoubtedly equate “Court” with Armani, Brooks Brothers, Theory, Layfayette 148, St. John’s, or, if you’re kinda broke (Gubment Lawyer, NonProfit), Kasper, Anne Klein, Tahari ASL, etc…LOL. Being facetious (kinda, sorta!).

  25. Angeline

    Non-lawyer sounding off here–I work at a nonprofit, which is business casual (with a little more leeway on the casual side if you don’t have a meeting to attend that day). I wear my riding boots about once a week or more, with skirts (both full and pencil, all right around knee length), dresses (again, knee-length), or skinny jeans (tucked in). I don’t know that I would wear them in a more formal office.

  26. k

    They just don’t look professional to me. I wouldn’t wear them to any court or administrative proceeding no matter how casual.

  28. mille

    I practice in a very casual jurisdiction, and we can get away with a lot– I’ve seen prosecutors wear jeans to court on Fridays, and I usually do trials in a non-matching jacket and pants, not a pulled-together suit.

    I think the boots would work with an a-line skirt and tights, and can certainly work with other dresses or skirts. I’ve seen other people wear knee-high boots to court a lot, and I don’t see why riding boots would be different.

    For me, the ultimate test is “do I feel confident in these shoes?”. Am I walking into the room with authority and confidence, ready to kick-ass? Do I look like a lawyer who can be trusted to be professional and do my job? Or am I worried about what I am wearing, uncomfortable sitting or standing in the boots for long periods, etc? If it makes you feel good, and you are in a court where suits aren’t required, you are fine wearing the boots.

    • Cynthia Kouril

      I think there is a difference between real riding boots, which because they are meant for the “heels down” position are not very comfortable for walking around in and which are made from thick leather.
      They don’e look like fashion.

      OTOH, are equestrian style boots made from thin supple leather. I can certainly see them in the office, and could see them in court during really cold or snowy weather.

      And I practice in federal court and the commercial parts in New York, mecca of formal dressing.
      Whenthe weather is nice, you wear a pump, but when the wind blows in lower Manhattan and the sidewalks are icy, the only way to get to court is boots and a equestrian style boot looks a heck of a lot more professional than moon boots or things you wear to the ski slopes.

  29. chix pix

    There’s a world of difference between fashion boots modeled on an equestrian theme – great for lots of places – maybe not for court except in rotten weather – and actual riding boots – which are for riding – period. Obviously you do not have to be “on the horse” to wear them….

    It’s like I will wear ballet flats to work – but they are not actual ballet slippers!

    • Seven2Seven8

      I am am attorney practicing family law in the Midwest. I agree with the prior poster that, for court, there are two questions: (1) How casual is your court and (2) How confident will you feel? I see a lot of cardigans and clogs in my divisions, so a really polished look with flat, knee-high boots isn’t a guaranteed flop by any stretch. Also, and especially so in the divisions where the judges have been on family law benches exclusively, your reputation is what matters first. And, I think there’s a big difference between a hearing or trial and a settlement conference or court errand. Most women wear suits for formal hearings, no matter how many times they’ve appeared before the judge. But for a pop-in conference? Cardigans and more casual footwear are fine where I practice. Every court, every jurisdiction is different.

    • coco

      I personally think the car coat looks more professional, but I think either would be fine.

  31. Ms B

    It snowed where I am yesterday and so I busted out my riding-style boots for the first time this season today — and wore them to federal court. They were accompanied by a straight black “boot skirt” that was a couple inches below the knee, a black long-sleeved shell, a houndstooth hacking-style jacket, and an Hermes scarf, with pearl jewelry. There is no question in my mind that the outfit was professional and appropriate.

    I think that the key here is that my boots have low heels (1″) and are pretty much unadorned (only one small strap and buckle near the top of the boot, and that does not show with the longer skirt). I would not wear boots to a “big” hearing, to an appellate court, or to a hearing with a judge that I have not appeared in front of many times. However, I am at that age where I have a more leeway, especially on a motion docket in front of a judge my age who knows me and who I appear in front of a couple times a month (and who was wearing boots herself today), so keep in mind that YMMV.

  32. Fresh JD in La

    I don’t see why wearing riding boots or other knee high boots to a somewhat casual office would be a problem if they are well styled, but I don’t really like the whole knee high boots to court look… I’ve interned at juvie court and while the standards are a little more relaxed I don’t remember seeing boots there. Granted, I live in Louisiana so inclement weather (for those kinds of boots) really isn’t a consideration, but I just don’t think it looks right. Also, I was in a district court today on a rule/hearing day and I saw two female attorneys in knee high boots and they looked terrible. Maybe it was boot choice and/or styling, but they just didn’t look professional. I’m not saying you have to be stuffy and wear a matching suit and boring pumps, but I think that people (not just women and not just attorneys) forget that a certain level of decorum and professionalism are required in EVERY court!Maybe I’m just too new to the profession and I’m taking things a little too seriously? I’m 26 and I just started practicing, but I make an effort to look put together and stylish even in this cold snap that we’re going through… Like today I wore charcoal gray slacks, burgundy v-neck sweater, with a charcoal gray blazer that had lighter gray and pink/burgundy pinstripes and some low black heels & I had a black/white but not quite herringbone overcoat.

    Ok, so I’ll get off my soapbox on that topic and move on to my next rant… I see so many inappropriate purses at court and it just drives me crazy! I’m not saying that you have to take fuddy duddy briefcases to court, but if you’re in a nice dark suit the look is totally ruined by your purple fake-patent leather hobo that has all these dangly things and papers sticking out of it… All I’m saying is that if you take it to the club, please don’t take it to court!

  33. BrieCS

    On the “built for specific purpose” thing – I don’t think we’d really have fashion if people didn’t wear things out of their intended use!

    I’d say for an office, yes. For court, not really… I’m no lawyer, but as much as I love fashion, I’d be a little confused if my lawyer was wearing riding boots. Other boots? probably not an issue. Riding boots are a different feel, though.

  34. Liz (Europe)

    With pants maybe, with a skirt I think they’re a bit too tall to even look good at all.

  35. Anonymous

    The Juvie judge is more than likely wearing a Marvin the Martian tie or something equally ridiculous, so I think riding boots are just fine for Juvie Ct. proccedings.

  36. Jaclyn

    I think it really all depends on what firm you work at or what type of court you are attending. The firm I work at at is really laid back, and Fridays are casual. Riding boots would be fine on casual Fridays. For court, I don’t really know. It really just depends on the court or case, I guess. For example, I’m sure you could get away with it if you were in a somewhat low-key court or case, such as small claims. If you’re fighting a more severe case though, I personally would not wear them in court.
    I’m only 20 and I’m just an intern, but I definitely wouldn’t wear my riding boots to court. Bottom line, if it’s casual Friday or you’re at a laid back firm, go for it. If you’re going to court, stick to the “front region” guidelines of the court. Most of you have an audience that expects a certain amount of professionalism from people in the legal profession.

  37. Erin

    I think if you do it like Condi did, you’re all set. (Although that’s assuming it’s slightly more casual. I wouldn’t wear them to court or a big meeting, but that’s in DC or NYC, where I usually practice.)

  38. Denise

    Riding boots aside,I wouldn’t consider them appropriate for court, unless under pants. I am pretty dam tired if the bashing if librarians and their wardrobes. It’s offensive and time to put the stereotype aside. As a corporate librarian, I have seen badly or unfashionably dressed people of all professions. Why is it acceptable to constantly denigrate us? In a profession dominated by women, who are in most cases considered to be highly intelligent and smarter than the general public what are you saying? You can’t be smart and well dressed. So is the flip side of that well dressed women aren’t too bright ? If anyone especially a man made that remark, you’d be highly offended. I think an apology is in order

  39. Judith Rasband | The Image Expert

    Where’s the horse? The look is confusing. Riding boots in court communicates you’d rather be some place else. Attention to the boots is also distracting. In court, all details of appearance should allow attention to go to your face for direct communication with the judge, the jury, whoever. Appearances are amplified in the courtroom which serves as a stage of sorts — all eyes are on you. Save the riding boots to signal your transition to terrific after-hours occasions.

  40. Stacey Rider

    As much as I’d love t say yes I think for court the answer has to be “No”. I have tons of riding boots both practical for riding and design riding boots and have pairs that are suitable for all kinds of occasions. However I think I would struggle to find a pair I would feel comfortable going to court in as a legal representative.

Back to Top

About

Work with Corporette®

Serious Stuff

work fashion blog press mentions