Chris Black, co-host of the popular podcast How Long Gone, has cultivated a distinctly preppy personal style centered on JM Weston penny loafers he’s worn for a decade, navy polo shirts and vintage Levi’s. The 43-year-old, who dresses more like his mother dressed him as a child than ever before, launched his own brand Hanover, which recently released a navy polo shirt after what he describes as a challenging search for the right pique fabric.

Black spent four years as a creative consultant at J Crew, where he worked closely with Brendon Babenzien, the former menswear creative director and founder of the brand Noah. Babenzien remains Black’s style icon—a fellow skater and music enthusiast with a grasp on East Coast preppy aesthetics that Black deeply admires. "Every time I see him he looks amazing," Black said. The podcasting world played a significant role in Black’s life during a difficult period—he was addicted to prescription painkillers in the early days of podcasting and listened to six hours daily before getting clean.

The former addict turned entrepreneur now hosts How Long Gone three times a week with Jason Stewart. His aesthetic extends to collecting vintage band T-shirts, capping himself at $500 per piece, with dealers on Instagram who know his size and taste. His most treasured item is a black REM Green T-shirt. Black favors listening through AirPods over vinyl, frequents Café Integral in NYC’s Nolita for cortados, and owns a Contax T3 camera he refuses to sell.