Regan is studying to go to law school to learn about nonprofit law. Because the entrance exam is no laughing matter, stressing about what to wear is the last thing on her mind. But she still manages to pull of a cool aesthetic that shows off femme sass with a hint of punk.

“I like to dress relaxed because I like to be relaxed,” Regan told Go Girl. “I like casual looks that aren’t trying too hard. I think fashion should be about the comfort you have with who you are.”

Shirt & Sweater: Forever 21
Jeans: Ross
Shoes: Converse
Bag: Steve Madden

$5 off