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GLAMOUR QUEEN: RACHEL ROY
"When I look at pictures when I was younger, I do the quintessential cringe," says ladylike fashion designer Rachel Roy, who spent her California youth "charging full-steam ahead" toward the trends of the day, i.e., Huey Lewis & the News blazers and Levi's 501s with cuffs folded over and rolled in trademark '80s style. "I probably saw it on George Michael or somebody," she says with a laugh. Nowadays, Roy's aesthetic is decidedly trend-averse, with influences that long predate her. "Tallulah Bankhead, Ava Gardner, Audrey, Grace," says Roy, rattling off a few of her favorite screen stars. "I find I'm an old soul." Her take on retro Hollywood's "strong femininity" usually includes pencil skirts, trenchcoats, blazers with exaggerated shoulders, sexy heels, and plenty of vintage costume jewelry, all worn with "red lipstick on a nicely defined lip." Now, with more than 20 years in the fashion industry—she got her first job at Contempo Casuals at age 14—she also knows what doesn't suit her 511 frame: "Skinny jeans—they could work for me if I were able to drop a quick 20, but I'm not, and that's okay." Ultimately, though, Roy's daily choices "have very little to do with anything besides how I'm feeling in the morning. I care about how you feel when you're wearing something, because I think that if you feel confident, you look beautiful. Someone's energy and aura and soul are so much more important—they don't compare to what you have on."