What They're Buying: Italian Wool Ludlow Suit, $650

What, do you expect this start-up founder/graphic designer/advertising creative to shop at BROOKS BROTHERS? Dressing up doesn't have to mean looking lame, and J. Crew gets that. Here, they are free to experiment by throwing a chambray shirt underneath a suit and pairing it with an artfully unkempt camouflage tie from The Hill-Side as well as a beat-up pair of Vans Authentics. After all, they are the adults now. They make the rules. You would walk into this guy's office and find like, every copy of Fantastic Man and a Saturdays magazine open on his desk.