The brand, which has collaborated with the likes of über-preppy Sperry Top-Sider and Manolo Blahnik (swoon!), is perhaps best known for its menswear — tailored suits and sharply cut shirts with a sporty undertone. Since 2007, however, the designer has been shaking things up with his new vintage-inspired women's line, Boy.

Band of Outsiders
Designer: Scott Sternberg
Launch: 2004
City: Los Angeles
Famous Fans: Kirsten Dunst, Jason Schwartzman, Kanye West
Signature Style: Quirky twists on classic staples