1. T-Shirt Chic
David’s basic black and white proves that less is more — except when it comes to V-neck depth.
2. Right Out of Bed
Caroline describes her day-to-day with three words: “work, work, work.” We want her boss to give her more days off so we can see this self-described “laidback” look more often.
3. Barely-There Leather
Daniel proves that “just the sleeves” is “just the look.” We think his shoes are pretty perfect as well.
4. Husband Pants
Nina borrowed her jeans from her husband, proving that every woman should raid her man’s closet more often. It probably works the other way around, too.
5. Zipped Down
Buck’s hoodie is exactly where we want it — on his body. A married man with a skateboard to boot, would you believe he’s a professional chocolatier? Because he is.
6. Geared Up
When asked about his personal style, Karim responded, “I have none.” But his camouflaged watch leads us to believe he prefers to keep some things to himself.
7. Day Owl
If Rebecca’s outfit doesn’t scream “marketing manager by day and DJ by night” to you, then you’re clueless and you should ask Rebecca to take you shopping. She’s a marketing manager by day and a DJ by night.
8. The “Exactly-What-You-Wish-You-Could-Pull-Off-But-Never-Could” Look
Boots! Belly! Overalls! Amanda described her style as “crazy, sexy, cool,” and there’s no arguing that.
9. Man Purse
Shay works the records as a professional DJ. More importantly, he works the man purse.
10. Tailored to Perfection
Self-described 198-year-old Jennifer, a Williamsburg filmmaker, sure knows what will read on camera. Her red leggings and frayed skirt will have you reconsidering Mom’s birthday present.
11. Scarves and Sleeves
Chris found the perfect look for those confusing-weather days. We love his long socks, double scarf, and sleeves. Well… “sleeves.”
12. Sultry Slytherin
Adrien’s bright demeanor might lead you to believe she’s wearing a floral print. But don’t be deceived: They’re snake heads. She’s all about the slimy beasts, and we’re ALL about her because of it.
We love Teddy’s bright orange watch, long scarf, and the fact that he, in true European form, knows who designed his shoes (Paul Smith). Teach us your ways!
14. “Not Trying”
Alan describes his look as “daring, vicious, and dark.” He makes it seem like he’s not trying, but you don’t pull off this look without some effort.
15. Skull and Bones (and Boots)
Caroline describes her look as “rough and tomboy” — traits that surely help her when things get aggressive at the thrift store.
16. Orange Is the New Pants
Sebastian wore orange pants. That’s all she wrote.
17. Nothing but Lips
Jessica’s red lips and long scarf pop against her black coat and boots. She describes her style as “lazy, comfortable, and easy,” but we don’t really believe her.
18. Laser Jesus
Roe’s “Laser Jesus” hat and Area-51 t-shirt prove that unlikely pairings can make for a great outfit.
Ananda and Annie were dressed to impress on their five-year anniversary. We don’t know whose boots we like better.