Most Stylish New Yorkers 2011: Bryan Greenberg

 Jim Spellman/

Name: Bryan Greenberg

Occupation: Actor; singer/songwriter

Sandal scandal: The How to Make it In America star — who calls his style "classic, calm, effortless, subtle, a little edge, raw and comfortable" — got his first style lesson when he moved to NYC at age 18: "No Tevas! I'm from the Midwest where all they wore in the 90s were Tevas and really baggy clothes. I learned fast that you can't get by on the same clothes in NY that you were wearing in St. Louis!" These days he sticks to J. Crew, Rag & Bone, Alexander Wang and Dior.

Big ticket item: "One of my most prized possessions is a vintage Rolex from 1955," says Greenberg, who is currently touring with singer Julia Sinclair to promote his February album, We Don't Have Forever. "I'd only had little calculator watches so I was looking all over for a real watch. I found this one at a store on the Lower East Side called Vain. I splurged."

Female Fashion: "I don't like when girls try to hard or reveal too much," says the HBO actor (season two of How to Make it In America premieres October 2). "I feel like girls in New York have a really good sense of style. I like the boots that come up a bit that show a little leg with a skirt and a sexy top. But then I also like it when seeing girls in cool t-shirts and baseball hats watching the game at a sports bar."

QUOTE: "I always had my own sense of style, I always kind of wanted to, express myself through fashion and look a little different then other people."

For access to all our exclusive celebrity videos and interviews – Subscribe on YouTube!