Hunter Parrish was in the running for the lead in High School Musical (and rumored to be the favorite)—a trilogy gig that would produce mounds of cash and fame for Zac Efron. But he pulled out. So it seems only fitting that in 17 Again, Parrish plays an insecure high school bully that repeatedly pounds on Efron. He’s not losing sleep over the lost millions though—afterall, those millions came at the cost of being typecast. A recent role in It’s Complicated put him in esteemed company with Alec Baldwin and Meryl Streep. Up next for Parrish is a sixth season playing entrepreneurial young pot dealer Silas Botwin on the Showtime hit Weeds.

Image via Peggy Sirota

Hunter wears a Band of Outsiders toggle coat ($1,800), Champion at Vassar College bookstore hoodie ($50), Steven Alan shirt ($168), Black Fleece tie ($150), Save Khaki khakis ($100), sneakers by Converse by John Varvatos ($110) and Smart Turnout socks. Read the entire GQ piece for more on this rising star.