#18 Scott Sternberg—190
WHAT: Designer, Band of Outsiders
WHY: Because under his direction, a sharply tailored brand of preppy geek-chic never looked so good. Because Sternberg has redefined how dapper guys and girls dress, sans gimmicks. And because he's managed to infuse a whole lot of sophistication, sex appeal, and swagger into a simple button-up. Go figure.
Photo courtesy of Scott Sternberg.