Rachel Antonoff makes clothing designed to spark a conversation or a double-take, with playful pieces featuring cross-sections of the female anatomy and prints of cartoon boobs (along with puns like “Color Me Badminton). In Rachel’s ready-to-wear fall collection, she even included a sweater that says “Seymour Pussy." As one of Lena Dunham’s pals, Rachel’s often seen with the NYC artsy crowd and has formed The Ally Coalition, an LGBTQ equality group, with the band FUN. She’s known for unveiling new collections in creative ways, and in 2015, Lena Dunham signed on to helm a short film, with all the characters wearing Rachel’s newest designs, including star Zoe Kazan.