After her 30th birthday, Keisha Sarpong made a promise to herself: No longer would the Denver-based stylist suffer through another 90-degree Colorado summer in stiff denim cut-offs—instead, she’d wear board shorts, which were more comfortable and better suited for her lifestyle. (Call it the third-decade effect, when your sense of self solidifies and acting on your individual agency becomes almost addictive.) Sarpong went on eBay, stocked up on vintage men’s swim shorts from Tommy Hilfiger, and hasn’t looked back since.
“I'm drawn to the functional details: the drawstring waists, paracord elements, baggier fits,” Sarpong says. “And as someone who wears a US 14-16, men's vintage board shorts, especially longer '90s silhouettes, tend to have less restrictive sizing.” Lately, she’s been wearing hers with button-downs, layered tank tops, and platform sandals—summer outfits that strike a balance between cowabunga and put-together.
