But we haven't had him down as much of a style icon, until now. He never dressed badly – he just dressed in an understated manner, and there's nothing wrong with that. But his outfit during a recent panel at Nashville's Wild West Comedy Festival caught our eye.
Nailing the collegiate/Americana look, Samberg wears a cool snapback baseball cap, an oversized aquamarine sweatshirt (sleeves pushed up, à la any 80s college movie hero worth his salt), skinny black jeans and a decent pair of Nike Air Max 1. It's a look that says 'KEG PAAAARTY!' with pride.