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LAST UPDATE: Wednesday November 25, 2009 11:10AM EST

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September 20, 1999
Vol. 52
No. 11

Will Smith

From PEOPLE Magazine Click to enlarge

"There's cool, there's fly, there's hot, and there's jiggy. Jiggy is way the next level," Will Smith told Britain's Observer newspaper last year. And when it comes to style, the 30-year-old actor-rapper definitely knows how to get jiggy with it. It's not easy to describe Smith's one-of-a-kind wardrobe (VH1's Roshumba calls it "homeboy meets high fashion"), but it's clear that this actor isn't about to settle for being a traditional man in black. "He's very individualistic," says 3rd Rock costumer Melina Root. "It's such a relief to see someone who takes pride in their clothes." The View's Francine Taylor thinks the 6'2" Smith uses his wild, wild wardrobe "to help show off his great personality," and she likes the way he frequently coordinates his outfits with those of his actress wife, Jada Pinkett Smith. "This is a man who loves clothing," says Audrey Style author Pamela Keogh. "He takes chances. And whether he's in jeans or leather or a beautiful suit, he looks like a guy who's having fun."

1. At the Grammys in L.A. last February, Smith won an award for Best Rap Solo Performance, but our judges think he deserves another for the number he wore to the show. "I love him in leather," says designer Pamela Dennis. 3rd Rock's Melina Root calls it "a great hipster look." Author Pamela Keogh thinks so too—but she issues a caveat for wannabes. "Will Smith can wear leather pants," she says. "Not every man can do that."

2. "You couldn't dress more perfectly for the premiere of a movie called Wild Wild West," says The View's Francine Taylor of the Robert Mata suit Smith wore to the L.A. event in June. "He seems comfortable," says Pamela Keogh. And A.B.S chief Allen Schwartz thinks the Western wear is very authentic. "He looks like Maverick," he says. "And I mean that in a good way."

3. The L.A. premiere of The Matrix in March brought out a coolly casual Smith (with wife Jada Pinkett Smith). "White pants and a leather jacket. It works," says Melina Root. Pamela Dennis also likes the simple style on the artist still known as a fresh prince. "I love him in this," she says. "He's just going to the movies."

4. "The hat, the down vest, the cuffed-up jeans—this is what Will Smith's all about," says Francine Taylor of the informal clothes the actor sported in Paris last December. "Love the homeboy-in-Paris thing," says Roshumba. Pamela Dennis says "oui" as well: "Perfect. I love everything about it. The hat is great."

5. Pamela Keogh likes that Smith "took a chance" when he wore this brown Halston tux to the NAACP image Awards in Pasadena in February. "It's a theatrical look, but it works on him," she says. "Very funky," agrees British designer Samantha Shaw. "You wouldn't expect him to wear a normal tuxedo." Adds Francine Taylor: "I like the satin finish."