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What boots are appropriate for the office in 2023? Have the rules changed for conservative offices — and for business casual offices? Buckles, cork heels, lug soles, harness straps, and more… let’s discuss.
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The Old Rule: Only Simple, Classic Boots for the Office
The old rule used to be that, for a conservative office, the boot should be as close to plain leather as possible. Simple! Not a conversation point! In years past we’ve talked about how any of the following items were best to avoid for a very conservative office:
- Decorative buckles and harness-type straps, whether on the toes, vamp, or tops of boots
- Decorative detailing, embroidery, or patchworked pieces, either in the same color/fabric or different color/fabric
- Shoes with a dip in the front, like cowboy boots (sometimes called a “curved topline”)
- Heels that are a different color from the rest of the boot, such as a brown wooden heel with a black suede boot, a red rubber heel on a black boot, cork heels, etc. I think I even remember some readers not liking a strip along the bottom of the heel, like this Blondo boot, that draws attention to the boot.
- Knee-high boots — YES, REALLY!! I still laugh to remember a conversation I had with a friend from law review, as we were taking BarBri classes — she had a tongue ring, for goodness sake! — wherein she suggested that only sex workers wore knee-high boots. This was actually a thing back then — Condoleeza Rice was accused of looking like a “dominatrix” in 2005 when she wore an all-black outfit with knee-high boots, and as recently as 2011 reporters wondered if Michelle Obama’s knee-high boots were appropriate for a Veterans’ Day service.
- Over-the-knee boots — Here’s our last discussion on OTK boots for work… I’m really curious where most people fall on these for work and other conservative environments in 2023! I wore some tan OTK boots to my youngest son’s First Communion last year, for what it’s worth (worn with a knee-length black dress), but it was a very small class.
What Boots are Appropriate for the Office in 2023?
Readers, what are your thoughts? Where do you draw the line for boots at the office in 2023? Which of your boots for the office are NOT simple leather without buckles, adornments, and more? Do you wear OTK boots to the office? (With skirts or pants?) What factors matter to you when you’re buying new boots to wear to work?
A few boots to illustrate the above questions, all from the NAS…

Stock photo via Deposit Photos / xcai.
Anon
To me, OTK boots still are very pirate-adjacent.
Anon
Same. Such a weird look and not office appropriate ever.
anon
+1
Rome Dining
I wouldn’t wear the cowboy style or lug sole tan suede ones to work but tbh I wouldn’t wear them anywhere as they look kind of dated to my eye.
The rest are fine, even OTK is not particularly eyebrow raising unless you’re pairing them with a miniskirt, in which case the footwear is not actually the problem.
Doodles
I think all of these are fine for my office now (if they are your style) except maybe the ones in the middle of that image with the weird protruding heel. It’s sort of business casual but really more like dress for your day. Law firm office of about 300 people in the midwest. None of these should be worn to court or to client meetings, but on other days, I don’t see an issue.
Anon
I refuse to think about boots in July :)
That being said, I can’t imagine a scenario in which over the knee boots are acceptable in the office! I also think the middle pair in this image looks too casual, but everything else would probably be fine in my office. Bottom left pair might be pushing it in my office, but personally I think they’re fine
Anon
I wore riding boots with harness details to work back then and never thought it was inappropriate! And I am a conservative dresser. (Not conservative politically)
Runcible Spoon
This winter I bought some paddock boots –lace-up, about 5 or 6 inches high, like mini “granny” boots — and I wore them with slacks and with dresses and they scanned just fine at my conservative government legal office. They are my favorite winter-fall-spring shoes now, super comfortable (as they are quite structured and supportive for riding horses) and straight out of the shoe box I could walk around the city all day without blisters. My other boots are knee-high, black leather, inside zipe, an elastic gore at the top for ease, and a sort of faux-horsey tackle/bit design around the ankle, and they have never seemed out of place at the government legal office. (Maybe I wouldn’t wear them in the courtroom, but maybe?)
anon
Certainly i will wear them come the cold but i feel like boots in general are not in right now? isn’t a more current look a loafer or oxford? i’m a middle aged lawyer, hardly trend setting but i haven’t worn a dress with knees boots in at least two years. it’s one of the reason i’ve moved into pants because i’m not wearing heels and i’m not sure what else i would wear with a skirt in the winter if not knee boots.
Runcible Spoon
I still do. I also have wanted some Condoleeza Rice moto lace-up platform lugged sole boots for some time and I would happily wear them to my government legal office and would strut like a million bucks! I wouldn’t care if they were several years out of date, and nobody would bat an eye.
Brittany v de engracio
i wear over the knee bootsboots exclusively high heels neutral colors with skirts , pants and dresses