#MattFriend has emerged as one of the finest—and certainly best-dressed—comedians of his generation. His razor-sharp impersonations have transformed him from online creator to bonafide entertainer, appearing with mic in hand at the US Open, the Oscars, and the White House Correspondents’ Dinner. Friend does it all in what’s become his trademark, suited-up look, a crucial sartorial choice that literally places him a cut above the rest. He was, afterall, declared “Best Dressed” in high school. For the Fall 2026 edition of Esquire’s Big Black Book, Friend gave us a preview of what’s to come while trying on some of this winter’s most essential new styles. See more at the link in our bio. Photographed by Jason Kibbler jasonkibblerstudio Styling by Nick Sullivan nicksullivanesq Grooming by Herve Claude hervecb Esquire Executive Design Director: Martin Hoops mhoopsdesign Esquire Visual Director: James Morris j_alexander_photo Esquire Editor-in-chief: Michael Sebastian michaeljsebastian