In a tiny diner turned studio in Silver Lake, shopper extraordinaire Tess Sullivan wears head-to-toe vintage: a Wrangler Western shirt, Levi’s, and black cowboy boots. Her style standards are exacting—as is her space, with ruthlessly edited, color-coordinated racks of leather jackets, blazers, trench coats, and dress shirts. Lifting a blazer lapel, her whole face brightens as she points out, “This one is hand-stitched.” She examines each piece with the discerning eye of someone who understands how clothes are made, honed by years of experience in the industry.
Sullivan’s entry into the fashion world was so wonderfully old school that it’s difficult to believe it happened in 2009. During her college years, Sullivan waitressed at Sam’s Grille, a strip-mall diner in Wynnewood, Pennsylvania. “People did not dress up to come in. The most expensive thing on the menu was a $10 chicken pot pie,” Sullivan recalls. But there was one regular couple who stuck out.They pulled up in a green Jaguar every Friday. He wore tortoiseshell glasses and three-piece tweed suits; she favored elegant polka-dot dresses. Sullivan was determined to wait on them. One day, she finally approached their booth to ask them: “Who are you and what are you doing here?” The man was Jerry Myers, the senior vice president of neckwear at Ralph Lauren. When Sullivan mentioned she was trying to land a job in fashion, he handed her his business card. Within weeks, she had a summer internship.