Who: Sabrina Shee, 19
What she's wearing: J. Crew shirt and pants, a Burberry pea coat, and Sperry Top-Siders. The bag and hat are from Urban Outfitters.
I like your hair. Why did you decide to go short?
"I'm going to my internship right now, so I figured I needed a 'business' cut."
Do you have any wardobe staples?
"I like the hipster-prep look, so Urban Outfitters and J. Crew. Anything comfortable."
Brooke says: When I first spotted Sabrina, I wasn't sure if she was a boy or a girl. But tiny details—such as the shape of the shiny check pattern of the jacket, and the ribbon on the cloche hat—are subtle giveaways of femininity, despite an overall masculine look. I liked the monochromatic but contrasting textures of her hat, bag, pants, and shoes.