1. SOPHISTICATED LADY: VANESSA WILLIAMS
Vanessa Williams knows from scrutiny. Crowned the first black Miss America in 1984, she weathered the subsequent nude photos scandal with a poise that would become her trademark. Today she's a showbiz survivor with a Broadway, recording, film, and TV career, geniously capped by her tart role as editor of a fashion magazine on Ugly Betty. Riffling through a stack of photos dating back more than two decades, Williams savors the memories, pronouncing her '80s looks "right on trend," tracing her black matte hose and oversize jackets to her days as a dancer—even admitting she once swore by Norma Kamali shoulder pads. ("Norma's stuff is still great!") But now Williams is more likely to be found in what she calls an "ethnic-sophisticated" look involving oversize knits, her favorite Hudson wide-legged jeans ("like pajamas"), a classic black leather jacket she's worn for three years, plenty of bangles, blouses from Ann Taylor, and the multicolored scarves she picks up in her travels. On her, this look reads no less glamorous than an electric blue number by North Beach Leather she wore over 20 years ago—"everyone was wearing electric blue leather!" she insists—but it better suits her life as bicoastal television star and suburban mother of four. Williams says her current style also draws on knowing what works for her body: "I have kind of boy hips, broad shoulders," she explains, meaning loose works better than cinched—and comfort is her first priority. One of the best ways to achieve that, Williams has learned, is to invest in really great pieces she'll wear for years, or an expensive shoe that won't mangle her foot. Not that it's always about cost. She still wears leggings, for example: "If my legs are in good shape, hell, yes!"
2. 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."
3. AMERICAN ICON: BROOKE SHIELDS
The first thing you notice about Brooke Shields, now 44, is that she could still stop traffic in a burlap sack. Four decades in the spotlight have left this all-American glamazon-next-door no worse for the wear, and she maintains a corresponding childlike awe about the glamour of the business that first made her famous. "Right now I'm so much more passionate about clothing than I ever was when I was really in the thick of it," she says, explaining that being dressed by professionals for years hampered the development of her own taste. (As a young model, Shields mostly focused on her schoolwork, which was "a way of separating this bizarre crazy world and me.") After graduating from Princeton, she found that whenever she did have to dress up, she never really felt comfortable in her own skin, doubting that what she was wearing was in fashion or worrying that it made her look too tall or too heavy. But Shields says the past few years—and a particularly patient stylist on Lipstick Jungle, Shields's recent NBC show—have triggered a thrilling coming-of-age. It started on set, when she began to pay attention to what flattered her body instead of always fixating on its imperfections. "I'm better off in things that are kind of dramatic," she says. "And I love myself in heels, I have to say." She now finds herself reaching for an eclectic but timeless mix of shapely cocktail dresses, low-rise trouser jeans, rocker boots, and blousy tops; rejects include "that sort of sloppy-chic thing" and anything with too much edge. Shields's sudden wealth of strong opinions has made shopping, once a cause for panic, a genuine pleasure. "Now it's easy for me to say, 'Yeah, it's nice, but it's really not me.'"
4. ROCKER CHICK: PATTI SMITH
In the poseur-glutted world of punk rock, pioneer Patti Smith, 63, has always been unique: a deep thinker, a poet, a sensitive soul who comes by her edge and attitude honestly. The very same can be said for her personal style, which she calls "expensive bum." Smith, author of the current memoir Just Kids, smiles as she recounts a recent trip to the upscale Manhattan department store Bergdorf Goodman. "I could see certain salespeople watching me," she says. "My hair's all a mess, or I look a bit raggedy. And I just laugh, because I have the most expensive clothes on! I just wear 'em to death." While she may not look it, Smith is a connoisseur of haute couture, which she discovered as a teen growing up in New Jersey, poring over the clothes in Irving Penn photographs in Vogue and scoring similar pieces at resale shops outside Philadelphia. But she was skinny, with stringy hair, during what she calls "that voluptuous blonde era," so Smith sought refuge in New York City's punk scene. Soon, she says, "half the girls who'd come to the shows would be dressed like me." Along with her insistence on "the thinnest, lightest, if-a-spider-wove-them-they-couldn't-be-thinner" T-shirts, Smith has maintained a love of coats; "they have a certain nobility about them." In the '70s, she bought oversize Armani and Versace blazers and wore them over her tees, which she held together with safety pins when they ripped (a few years later, every punk fan in New York was doing the same). Of her unique style, Smith says, "I took a little from Keith Richards, a lot from Bob Dylan. It's fun, you know?"
5. MIX MASTER: KELLY WEARSTLER
As anyone who has ever stayed in a hotel designed by Kelly Wearstler—or flipped through one of her over-the-top coffee-table books—can attest, the petite Los Angeles megadecorator is no minimalist. Her zany, upbeat aesthetic plunders Hollywood's past and recasts it in Technicolor, ignoring conventional wisdom about what matches, instead combining accessories and found objects into surprisingly harmonious tableaux. Arriving on set in jeans and a ponytail (one hardly recognizes her in this sedate getup), she surveys a rack of clothing and instantly zeroes in on a short white skirt made of feathers to pair with her own leather fringe wrap and vintage snakeskin boots. But Wearstler wasn't always such a freethinker. Growing up in Myrtle Beach, a world away from the Hollywood mansions that would later become her canvas, Wearstler mostly stuck to good-girl basics, occasionally scouring vintage stores and her mother's closet for things to add a bit of wit. "I was definitely more insecure then," she says. "But I would take risks here and there." It was only when she interned at the design firm Milton Glaser in New York City during college at the Massachusetts College of Art and Design that Wearstler started allowing herself to just let it all hang out, making "emotional" purchases at flea markets and gaining confidence in the madcap aesthetic that would become her signature. Before taking her sons to school, Wearstler has just 25 minutes to pull herself together, which she says facilitates fearless dressing. "Beautiful things happen," she notes, "when you break the rules and go for it." 4 tips for creating your own signature style