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Being a celebrity has always involved jetting from one destination to the next, but that didn’t always mean perfectly coordinated, accessorized-to-the-max airport ensembles. In the pre–brand ambassador days, the famous were allowed to have off-duty moments without the aid of a stylist. When Kate Moss stepped out hand in hand with Johnny Depp in madras pants and a white T-shirt, her outfit was selected for its comfort not its paparazzi appeal. Likewise, fashion icons like Linda Evangelista, Christy Turlington, Cindy Crawford, and Naomi Campbell all traveled chicly but in clothes that seemed entirely personal—who but Campbell would be diva enough to exit a private jet in metallic heels and carrying a Louis Vuitton hatbox?
Supermodel moments aside, there’s a lesson to be learned from a low-key approach to travel dressing. By keeping things simple, classic, and attuned to their personalities, the stars of that time created looks that are wearable even today. Crisp white shirts, cream-color trenchcoats, and logo-covered luggage never cycle out of fashion. We may be two decades away from the days when Gwyneth Paltrow and Winona Ryder personified squad goals, but their matching minimalism still registers as cool. The next time you’re headed out of town, take a page from the ’90s playbook and embrace the appeal of the understated.