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’s Boots ($85; sizes 34 to 41) are made from vegan leather, and come in black, light brown, and dark brown.
I love all of these outfits so much. Doreen, you look SO SHARP in literally every picture!
Thank you so much!
I want these.
I want these! Too bad shipping + customs to Europe make them unaffordable for me. Love the looks <3
As someone in Canada where it is already miserably cold and snowy, I am *so* jealous. You look so amazing. Look 5 is definitely my fave!!
1. Doreen you look so great!
2. I am now having so many dreams about the ways I can style these boots. I have check into sizing!
Thanks for this post.
Thanks, Carmen! Happy shopping!
WOW this is great!!
DAY TRIP FLY <3
obsessed with all of these Doreen, especially your fun socks! :)
I might need to know more about that hat…
I love all these looks! I WANT THESE BOOTS!
I continue to die a little every time I see how good these looks are
VEGAN LEATHER!!! I was scrolling all the way down going “maaan, these are so great, if only they were vegan” AND THEY ARE THIS IS CHRISTMAS <3 <3 <3
I have been eyeing these boots for a while, but can we talk about your jeans in 1 & 2? I love these! I am searching for a pair of straight leg/boyfriend jeans that don’t make me look like a weird lump…
You sure make those look great. Tempted to get a pair.
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
i love thissss
SO GOOD. I can’t pick a favourite. And may I say I have never seen double denim look so sharp.
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 :)
What exactly is vegan leather?
Can you describe the consistancy?
Also- the sizes are a bit smallish. I know a lot of younger women who have size 42.
these looks are amazing! and i have a pair of their blue brogues and LOVE them. will be getting another pair from them — maybe these boots! — soon.