You might guess that the personal style of Jenna Lyons, the bright and charming creative director of , would be right in sync with the classic American clothier, where every wristwatch is set to "timeless." But Lyons, it turns out, has a quirky, vivacious side and a personality that seems just as much Holly Golightly's Tiffany. She has a yen for the outlandish vintage jewelry of , and a soft spot for the camera—but mostly because it's a special edition she found in Japan. She loves her 1969 Mercedes for its pickup, or rather, lack thereof, and her husband Vincent Mazeau's 1969 El Camino because she has received marriage proposals while driving it. She has never met a sequin she didn't like, and in the Brooklyn townhouse where the couple live with their son, Beckett, 3, her wall of shoes is something of a shrine. But Lyons's feet are firmly on the ground—proof that the classics need a whiff of fun and wit. Otherwise, timeless turns into yesterday's news.