Riding Boots … to the Office?
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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.
Can You Wear Riding Boots to Work?
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.
(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?
Our Latest Favorite Flat Knee-High Boots For Your Commute
Hunting for black knee-high boots? Some of our long-standing favorites (as of 2025) include La Canadienne, Sam Edelman, and Sofft; also check this J.Crew bestseller, this Cole Haan option, and Vivaia for comfort.
Hi Stacey! I really think it depends on your town, your court, your judges, and the type of law you do. I wear riding boots under pants and with dresses to court from time to time – I probably wouldn’t for a formal setting (trial), but with a pulled-together outfit, I’d often be more professionally dressed in a dress, cardi, and riding boots at a settlement conference than some other attorneys who practice in my court/practice area/town. Really, the biggest disincentive is taking them off to get through security – if I don’t wear them, that’s usually why.