Sure, you only know Gossip Girl from your girlfriend’s Tivo priority list. But you have to admit that Chuck Bass character has an enviable wardrobe. New York line Unruly Heir makes us feel like we all can pull off that same trendsetting aesthetic. Blending inspirations of English prep and downtown ease, Mr. Bass could very well be the mascot for Unruly Heir—if he had a slightly more approachable vibe.

From tailored jackets to conversation-starting tees, Unruly Heir crafts what we like to call rebellious basics. The Pan Handle Tux Jacket worn over the Holly’s Print T-shirt embody the aptly named Fall 2008 collection of “Sidewalk Swindlers and Socialite Scoundrels,” breaking down the barrier between those who have a barely tapped trust fund and those whose lives are a nonstop hustle. Bad boys (and closet Gossip Girls fans), unite!