TRY AS YOU MIGHT, in fashion, you can’t outrun the past.

Believe it or not, the grungy, 1990s-style men’s denim trend is back. 

Though he wasn’t born when Soundgarden first hit the airwaves in the late ’80s, Josh Galdo, 26, a nurse in Las Vegas, is drawn to hole-ridden jeans like the ones so many Seattle bands wore in the ’90s. “Probably one of the biggest style icons, Kurt Cobain, always wore slouchy, loose-fit destroyed jeans, but it looks so comfortable on him,” said Mr. Galdo, who owns worn-out jeans from brands like Nudie Jeans, Naked & Famous Denim and Levi’s.

Distressed denim aligns with a current, sometimes comical taste for worn-in goods that look as if they’re one tear away from the garbage bin. On clothing resale sites such as Grailed, paint-splattered sweatshirts sell for well over $100, and Instagram sneaker-customizers have lately been painstakingly “aging” new Jordans to masquerade as pairs from the ’90s.