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One Pair of Tomboy Toes Boots Five Different Ways

This post is sponsored by Tomboy Toes.

What’s better than a great pair of ankle boots? A great pair of ankle boots made for queers by queers! Below, Doreen Pierre of Dapper Penniless shows five versatile ways to style The Barrister’s Boots by Tomboy Toes.

Look 1: Double Denim

It’s nice when you can roll out of bed and run errands in an outfit that’s simple, comfortable, and still stylish. Denim on denim is my go-to for this; it gets a bad rap, but it’s actually easy to do right! I usually choose light denim on top and slightly darker denim on the bottom, then break it all up with a crisp white t-shirt. These boots add a sleek, sexy feel to the look, as do my aviator glasses that make me feel like a rockstar!

Look 2: Fall Into Flannel

If I have one cool weather staple, it’s definitely my plaid flannel button down; it’s soft, warm, and good-looking, too. Just add boots, a cleanly cuffed pair of jeans, and a five panel hat, and you’re ready to toast s’mores around a campfire.

Look 3: College Casual

I always look forward to fall’s cool air and color-changing foliage, and it always makes me reminisce about returning to school after the summer — so for this look, I’ve combined classic preppy pieces with my favorite fall color: burgundy. Paired with my boots are burgundy chinos, a burgundy and grey striped skinny tie, and a subtly patterned blue button down. I’d wear this look to class or for a casual day at work, with either a textured neutral-colored vest like the one in this photo, or a blazer in colder weather.

Look 4: A Little More Formal

This is what I’d typically wear to functions like business meetings, fancy dates, or weddings. I love a shoe that can shine on any occasion, and The Barrister’s Boots don’t disappoint! I styled them with navy blue slacks, a blue button down, and a tailored grey blazer — plus a dark floral tie for a little extra flair. Who says florals have to be a spring thing?

Look 5: Day Trip Fly

Anyone who knows me knows I love color and patterns; that’s why I styled this look with coral chinos, a heather grey sweater, a jean jacket, and a patterned neckerchief. I’d wear something like this on a day trip to enjoy nature with friends, or for an adventurous date — layers keep me ready for whatever the weather may bring, and attention to small details puts the styling on this outfit over the top.

Tomboy Toes Barrister Boots

Tomboy Toes’ Barrister’s Boots ($85; sizes 34 to 41) are made from vegan leather, and come in blacklight brown, and dark brown.


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Doreen Pierre

Doreen Pierre is a fashion writer and multi-hyphenate creator based in Brooklyn, NY. Using fashion to represent her confidence and individuality, she prides herself on looking smart and stylish. You can follow Doreen’s journey through her instagram @itsdoreenpierre

Doreen has written 3 articles for us.


  1. i love everything about this article. i might use look 3 exactly as is, because i think i already own nearly everything for that and i’d just never thought to put it all together! omg. this article <3

  2. I first saw a post about Tomboy Toes on reddit…and then I googled them and read an awesome interview on DapperQ. So I bought a pair of the Downtown Dapper Oxfords and they fit great! They seem to be well-made, and it’s awesome that they’re vegan. They’re a dark enough color that they go with different clothes, but they’re a nice shade of brown that does show-off a bit :)

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