Photograph by Matthew Worden.

Pepper Watkins

Historic-preservation and urban-planning consultant

“Pepper’s a huge fan of The Sartorialist, a fashion blog that really helped him define his classic style. He also pays close attention to fit and proportion because he’s so slender. He hit the jackpot a few years ago when he came upon a trove of his great-uncle’s old Western-style shirts in an attic. It gave him a leg up in the hipster-wardrobe department.”

—Becca Glover Watkins, Pepper’s wife and an account director at 3 Dog Agency