36. Freshjive "Don't Tread On Me"

Released: 2008

The classic Cali brand demanded liberty or death with this summer T-shirt that resurrected the Gadsen Flag, a symbol of resistance dating back to the Revolutionary War.

Lil Wayne famously rocked Freshjive's matching "Don't Tread On Me" fitted hat in the "A Milli" video. With some red skorts, or whatever the fuck those were.