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The Most Stylish VMA-Nominated Videos

Twenty-five classic looks, from Michael Jackson’s zombie attire to Britney Spears’ school girl outfit

The Most Stylish, VMA-Nominated, Videos, music videos

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Twenty-five classic looks, from Michael Jackson's zombie attire to Britney Spears' school girl outfit

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Britney Spears, ‘…Baby One More Time’ (1998)

Filer under: the quintessential teen pop video, regardless of era. Also: one of the most tantalizing song compositions to feature a piano riff, and certainly the only one with lyrics euphemizing puppy love as bondage — those innuendos purred out by a 16-year-old, no less. Most importantly: the serendipitous debut of Miss Britney Jean Spears, the doe-eyed Louisiana moppet who would reign the official teenage dream queen of Y2K pop only a year later. Even if she never released a second single, "…Baby One More Time" was a monster, a history-making hit on both radio and MTV. The song's video popularitywas buoyed significantly by the controversy sparked by Spears' choice of wardrobe: a tarted up school-girl uniform, later revealed to be purchased at K-Mart. The video earned three VMA nominations the following year, winning none. At later points in her career, she bravely pioneered other tricky costume ideas, giving snakes, red cat suits, and diamond-encrusted body stockings a go. But it will always be the school-girl uniform, and "…Baby," that defines the precocious promise of our early love affair with Gen Y's most fiercely adored icon.

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TLC, ‘No Scrubs’ (1999)

Continuing the  futurist visual plight of Michael and Janet's "Scream" video,  TLC's "No Scrubs" was a Hype Williams-helmed tour de force. The year was 1999, and every act was doing their best to appear "modern," but no other mainstream group took it to TLC's level. Chili, T-Boz, and Left-Eye are decked out in resplendent wigs and their finest space-age apparel, remembling Japanese cyber-punk heroines as they traverse a severely white universe divided up into three thematic microcosms, all seemingly sponsored by Ikea in the year 2050. The clip won instant accolades for its clever execution, earning 6 VMA nominations in 1999, and winning Best Group Video.

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Christina Aguilera, Lil’ Kim, P!nk, Mya, ‘Lady Marmalade’ (2001)

For their Moulin Rouge! themed remake of LaBelle's classic "Lady Marmalade," Christina Aguilera, Lil' Kim, P!nk, and Mya had to play the cards they were dealt: when singing about the exploits of a heroic New Orleans tramp, you do as Mlle. Marmalade does — you gussy up in lingerie. They all managed to put their own unique twist on the negligee lace and garter belt prototype, with P!nk keeping her signature hair shade, Mya looking like a 20s era Pigalle coquette, Lil' Kim defying all conventional boudoir reference points, and Christina Aguilera concurrently trying them all on for size. This is the video some remember caustically as Xtina's "Dee Snider" moment, but even haters could not deny the enormity of the song, which landed majestically at #1 on charts on both sides of the Atlantic, where it remained for a generous part of the summer. In September, it won Video of the Year and Best Video from a Film at the VMAs.

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No Doubt, ‘Hey Baby’ (2001)

Wherein a 32-year-old Gwen Stefani tries on dancehall, houndstooth, grafitti, fishnet, and pigtails for size — and pulls it off with charm. No Doubt quickly brushed off the dismaying chart performance of 2000's  Return of Saturn by releasing Rock Steady, a hedonistic record fueled by their recent obsession with Jamaican party music, Prince, and U.K. electropop. To suit the sound overhaul, the band's image had to undergo its own makeover. The result was dizzying: customized band logos (influenced by the graffiti of Stephen Sprouse), houndstooth and argyle patterns (a nod to British mod and Two-tone prep), and a ton of red, yellow, and green (traditional Rasta hues) swiftly defined the look of No Doubt in their feel-good renaissance. All motifs are present and accounted for in "Hey Baby," the band's comeback single and video, which won two VMAs in 2002 for Best Pop and Best Group Video.

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White Stripes, ‘Seven Nation Army’ (2003)

Among the fashion rules The White Stripes regularly disobeyed: dressing uniformly in red (regardless of season), the general laws of black hair dye, and that unspoken rubric about not dressing in the same outfit as your sister, er, wife. But with "Seven Nation Army," the blues rock duo proudly proved an old Wive's expression true: "red on black is a friend of Jack."  The Alex and Martin-directed clip feature Jack and Meg situated inside an infinite tricolored, triangular kaleidoscope of surreal imagery. The 2003 single truly put The White Stripes on mainstream turf, earned them critical acclaim, and landed them four VMA nominations and one win (for Best Editing).

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Beyonce, ‘Crazy in Love’ (2003)

For Beyoncé's official coming out party, she pulled out the big guns, hiring Rich Harrison to produce, future husband (and now father-to-be) Jay-Z to rap, and Jake Nava to direct its vivacious video. Only 21 at the time, the singer celebrated her foray into adulthood and independence by channeling an icon – James Dean. "I wanted to be a female version of [him] and wear an iconic white T-shirt and jean shorts," she told W this year. Red pumps, now a part of pop visual history, were the perfect complementing piece – B jokes that dancing in them was the ultimate victory, though we suspect the outrageous success of her debut single – Number One just about everywhere, the most acclaimed single of the year, one of the decade's defining hits — felt pretty nice, too. VMA recognized Beyonce's sterling solo effort by awarding it three VMAS — Best Female Video, Best R&B Video, and Best Choreography.

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Outkast, ‘Hey Ya!’ (2003)

This is certainly Outkast's most incandescent video statement — no small feat, as they've left many in their wake. André 3000 ostensibly funneled inspiration from a melange of sources — A Clockwork Orange,  The Beatles on Ed Sullivan, St. Patrick's Day (hence all the vivid green). He plays eight versions of himself, all members of the fictional group "The Love Below." All are attired in Old Estate chic: argyle, pantaloons, white socks, pinstripes and plaid run rampant throughout. The video reputedly inspired André 3000 to start his own clothing line, Benjamin Brixby, a few years later. For 2004, a Video of the Year trophy, alongside 3 other VMAs and a Grammy months later, provided Outkast all the love they needed to imbibe.