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| Timberlake performed "Like I Love You" solo at the MTV Video Music Awards in an oversize suit with leather cuffs. His fedora and sneakers would prove to be signature accessories. (CREDIT: Theo Wargo/WireImage) See All of Justin's Looks |
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| Crimes of fashion, boy band style! Timberlake wore an oversize blue tweed jacket with--what else?--matching paisley velvet trousers. He and his fellow group members celebrated their self-titled debut album at the Billboard Awards. (CREDIT: Jeff Kravitz/FilmMagic) See All of Justin's Looks |
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| Nothing says love like matching outfits--Timberlake coordinated with then-girlfriend Britney Spears for the American Music Awards. "They do a lot of denim," stylist Rachel Zoe told People. "They have things custom-made in denim with denim studs, denim tie-dye, dazzle denim." (CREDIT: Jeffrey Mayer/WireImage) See All of Justin's Looks |
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| Read his chest: "Nasty." Timberlake performed "Pop" alongside his group at the MTV Video Music Awards in a graffiti-sprayed getup. A bedazzled Dolce and Gabanna belt provided a not-so-subtle finishing touch. (CREDIT: Kevin Kane/WireImage) See All of Justin's Looks |
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| Timberlake performed "Like I Love You" solo at the MTV Video Music Awards in an oversize suit with leather cuffs. His fedora and sneakers would prove to be signature accessories. (CREDIT: Theo Wargo/WireImage) See All of Justin's Looks |
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| JT flaunted some major rocks--solitaire earrings and an initial pendant--at the Soul Train Music Awards. He kept the rest of his red-carpet look casual, layering a suede bomber over a hoodie and herringbone trousers. (CREDIT: Gregg DeGuire/WireImage) See All of Justin's Looks |
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| He scruffed up a suit at the Grammys (where he picked up two awards) with stubble, sneakers and a salmon shirt. (CREDIT: Dan MacMedan/WireImage) See All of Justin's Looks |
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| Timberlake brought out his baby blues at the MTV Movie Awards with an azure sweater. (CREDIT: Steve Granitz/WireImage) See All of Justin's Looks |
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| Looking sexy and grown, Timberlake rocked a silver Prada suit at the Grammys. He won two awards for cuts off of "FutureSex/LoveSounds." (CREDIT: Jon Kopaloff/FilmMagic) See All of Justin's Looks |
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| Proving his knack for clever layering, Timberlake sported a leather bomber over a shirt and tie at the L.A. premiere of "The Love Guru." (CREDIT: Steve Granitz/WireImage) See All of Justin's Looks |
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| He's his own best model! Timberlake promoted his clothing label (with co-designer Trace Ayala) William Rast at the Fashion Rocks concert. (CREDIT: Dimitrios Kambouris/WireImage) See All of Justin's Looks |
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| He celebrated the 100th anniversary of Cartier by adding carats and carats of the brand's diamonds to his tweed William Rast suit. (CREDIT: Bryan Bedder/Getty) See All of Justin's Looks |
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| JT went Clark Kent chic at the Costume Institute Benefit Gala in retro specs and a bespoke William Rast tuxedo. (CREDIT: Rob Rich/Everett) See All of Justin's Looks |
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| Looking every inch the serious actor, "The Social Network" star wore a double-breasted cardigan and waxed denim jeans to the Cinema Society screening of the flick. (CREDIT: Jim Spellman/WireImage) See All of Justin's Looks |
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| Timberlake got sartorially professorial at a London event for "The Social Network" in a narrow tie, tweed vest and dark-rimmed glasses. (CREDIT: Jon Furniss/WireImage) See All of Justin's Looks |
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