Wardrobe-wise, it’s helpful to have family members in high--fashion places. Just ask Dylan Brant, the oldest son of the supermodel Stephanie Seymour (with the musician Tommy Andrews) and half-brother to toffs about town Peter Brant II and Harry Brant. “Between my mother and them, I have the best stylists in the world,” he says. A senior at Bard College and a cofounder of Young & Starving, a nonprofit organization that supports emerging artists, Brant doesn’t spend much time thinking about his attire. But his brothers do. “At night, I wear a Dior or Dolce & Gabbana suit that they’ve picked out,” he explains. “During the day, I have more of a James Dean thing going on—jeans, T-shirt, Dior Beatle boots that Harry bought me for my birthday.” The sartorial benefits extend to his girlfriend of a year and a half, Chloé Perrin (no relation to Sebastien), the New York–based brand director of Perrin Paris, her family’s leather accessories house. Among her favorite pieces in a closet replete with high-end collectibles is a black Azzedine Alaïa dress that the designer (who is a close friend of Seymour’s) gave to her. She has also acquired a handful of sleek avant-garde “staples,” as she puts it, from her mother, Sally, including a Jil Sander bustier suit and a Comme des Garçons asymmetrical dress, which she pairs with a Perrin signature Capitale clutch (a style equipped with a fingerless glove on its flap, for easy carrying) and Martin Margiela Tabi boots. “There’s definitely an edge to my look,” she says.