Black suit and silk tie: Emporio Armani. Flannel button-up shirt: American Apparel. Silk pocket square: Tom Ford. Pink sunglasses: Darrencriss.com. Photo by Mitchell McCormack. All photos styled by Ashley Phan-Weston.

Shirt: American Apparel. Vest: John Varvatos. Sunglasses: Darrencriss.com. Photo by Eric Silverberg.

T-shirt: American Apparel. Jeans: Levi's 511 skinny. Sunglasses: Darrencriss.com. Suspenders: Darren's own. Photo by Eric Silverberg.

V-neck t-shirt: American Apparel. Jeans: Levi's 511 skinny. Guitar: Fender. Photo by Mitchell McCormack.

Trench coat: Uniqlo. Sweater: John Varvatos. Striped polo: stylist's own. Jeans: Levi's 511 skinny. Shoes: Rockport. Guitar case: Gibson. Photo by Eric Silverberg.

Trench coat: Uniqlo. Sweater: John Varvatos. Striped polo: stylist's own. Jeans: Levi's 511 skinny. Shoes: Rockport. Guitar case: Gibson. Photo by Eric Silverberg.