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Nicole Richie’s Personal Style Dos & Don’t’s: “You Have to Have a Sense of Humor”

The street-style master and star of #Candidly Nicole gives one lucky fan (and you!) a quick fashion tutorial.

Nicole Richie, 33, knows a thing or two about changing your personal style. The former Simple Life star transitioned from a Los Angeles socialite whose uniform of choice was chunky highlights and teeny-tiny minis to a full-on fashion icon known for her cool, tailored looks. (“Nicole Richie just pisses me off, she’s so good,” Rihanna told Glamour last year.) Along the way she launched a fashion company, House of Harlow 1960, and landed her own series, #Candidly Nicole (back on AOL this month and VH1 in June), based on her unfiltered tweets. One recent gem: “Are death threats more effective via text or email? Trying to find my sister.”

P.C. she’s not. But her cutthroat honesty has won her many fans (almost 5 million Twitter followers, if you’re counting), including Glamour reader Cara Hille, 29, who so admires Richie she once dressed as her for Halloween. Since Richie obviously has great style advice to dole out, and Hille, a fashion student in L.A., hopes to land a job in the industry once she graduates, we thought, Let’s get these two women together! Richie was happy to give Hille some getting-dressed tips; she even brought along a few items from her personal closet. Listen, look, and learn.

Think business attire has to be boring? Not so, says Richie. “We’re in a different time now. You can’t be so serious about fashion,” she told Hille. “People really appreciate personal style. For work I throw on a lot of jewelry.” That’s a liberating perspective for Hille: “The people who surround me have always encouraged me to be a little bit more conservative on a job interview,” she admits. “Hearing Nicole say that makes me think about adding some color or an element that shows my personality.” Jewelry is an easy go-to; try a simple sheath dress with a statement necklace.

Hille herself has never been a fashion conformist: “My sister got me a pair of bell-bottoms when I was in the third grade, and everyone said, ‘What are you wearing?’ ” she recalls. “Instead of being like, ‘Oh no, I shouldn’t have worn these,’ I was like, ‘Perfect!'” Richie is all for that rebelliousness; her mother, Brenda Harvey Richie, “was a lay-dee—she forced me to wear a lot of dresses,” Richie says. “But we have very different styles.” That’s part of the reason she started her own line: “I wanted to get back to that feeling of the sixties and seventies. You could clash. You could mix prints. You can do all of that.” To still look pulled together with different-style pieces, find a common theme: Want to wear tribal patterns with menswear checks? Choose prints that share similar colors.

Tall, short, hourglass, curveless—it’s all good, according to Richie. “If I don’t want to wear high heels, then I’m not going to,” she says. “I’m 5’1″. Even if I wear five-inch heels, what’s the tallest I’m going to be, 5’6″? Who’s that scaring? Nobody. So I’ll wear flats and just be full-blown in my shortness rather than try to be somebody I’m not. And there are plenty of outfits that I’ll try on and be like, ‘Wow. This is a beautiful, sick, sexy dress. This would look much better on somebody tall than it would on me.’ And that’s fine.” Of course, figuring out what works for you takes time. Recalls Hille: “Nicole was like, ‘I don’t nail it the first time. I try things a bunch of times, and when it works, I know.'”

Richie’s number-one takeaway: “You should never feel bad about yourself because the trend everyone is wearing doesn’t fit you,” she says. “There’s nothing cooler and more attractive than being 100 percent, authentically you. As long as you’re doing that, you’re winning.”

Jan 2015 – Glamour