By Wonderwall.com Editors
3:00am PST, Feb 16, 2024
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Jennifer Lopez is taking a look back at her search for love in her ninth studio album, "This Is Me… Now," and its corresponding Amazon Prime narrative musical film and visual album, "This Is Me…Now: A Love Story." Both debut on Feb. 16, 2024. To mark the occasion, we're taking a look back at J.Lo's best and worst retro fashion moments from early in her career, starting with the fantastically '90s look that she wore to the Oscars in 1998…
Keep reading to see it in all its glory, then read on for more of her most fantastically dated retro fashion moments…
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Jennifer Lopez donned this delightfully dated Badgley Mischka dress with cap sleeves at the Oscars in 1998. Her styling would've been very on-trend at the time: She rocked silvery eyeshadow with dark lipstick in a neutral hue, stick-straight hair partially pulled back with loose layered wisps in the front, plus a chandelier choker.
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Jennifer Lopez's most memorable look of all time? The green palm-print Versace dress with a dangerously low-cut neckline that she wore to the Grammys in 2000. It might be retro, but it still holds up today — on her, at least!
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It's one of her most famous ensembles ever: Jennifer Lopez wore a white Sean John crop top with white boot-cut jeans and a white bedazzled bandana as a headband at the MTV Video Music Awards in 2000.
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Jennifer Lopez rocked a puzzling look — cream trousers, a white bralette and an oversized cream blazer, plus a white cowboy hat — at the 1998 MTV Video Music Awards.
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Yikes! Jennifer Lopez paired a sheer animal-print off-the-shoulder peasant top with black leather short shots, black thigh-high leather boots and a beige floppy hat at the 2001 MTV Video Music Awards.
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Jennifer Lopez looked so '90s at the 1998 MTV Movie Awards in a slinky silver halter top with a leather maxi-skirt. Our favorite part, though? The two blinged-out barrettes she wore in her hair. It doesn't get more '90s than that!
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Jennifer Lopez — who was still with first husband Ojani Noa at the time — opted for a mature look at the 1997 Oscars. She wore a sparkly Badgley Mischka gown with cap sleeves, big barrel-curled hair and dark lipstick.
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A vision in white! Jennifer Lopez showed off her enviable abs in a matching white skirt and crop top at the launch party for her "On the 6" alum in 1999.
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Jennifer Lopez wore her hair in tight ringlets and sported neutral makeup at the 1998 premiere of "The Man in the Iron Mask." Could you imagine her in a strapless zig-zag-pattern dress like this today?!
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Jennifer Lopez covered up in a matronly floral-embroidered dress at the 1997 Independent Spirit Awards.
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Jennifer Lopez sported an incredibly ill-fitting black leather look at a 1997 fashion benefit.
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Jennifer Lopez wore a flimsy little white dress that was oddly cinched at the middle at the 2001 American Music Awards. She topped off her look with a floppy white hat.
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Jennifer Lopez chose a black gown with a train for a 2005 Macy's event.
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Jennifer Lopez disappointed at the 1999 Met Gala in a sparkly long-sleeve knee-length dress with a plunging neckline. She completed her look with a single diamond necklace and silvery eyeshadow.
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Pretty in pink! Jennifer Lopez rocked a raspberry-colored halter dress and wore her hair in a half-up hairstyle at the 2000 ALMA Awards.
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Jennifer Lopez opted for a conservative — and very shiny — look at the 1998 premiere of her film "Out of Sight." She wore a floral bolero jacket over a champagne-colored dress and accessorized with low pumps.
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Jennifer Lopez glittered in a gold minidress at the 1999 Grammys. She wore her stick-straight hair parted down the middle — a style that was all the rage at the time.
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Jennifer Lopez wore a blush Vera Wang gown with tiered ruffles down the skirt at the 2002 premiere of "Maid in Manhattan."
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Jennifer Lopez was literally glowing at the 2004 Golden Globes in an orange Michael Kors gown with silver straps across the waist.
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Jennifer Lopez looked a little eccentric at a Dolce & Gabbana party in 2003 in a pink-hued headscarf and a champagne-colored jacquard coat over a blue dress.
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Jennifer Lopez wore a furry white bolero jacket over a beige dress with a plunging neckline at the London premiere of her movie "Maid in Manhattan" in 2003.
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Jennifer Lopez wore her hair in tight curls and rocked a bizarre black ensemble — an asymmetrical skirt with a button-down blouse that she left mostly unbuttoned — at the 2002 MTV Video Music Awards.
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Jennifer Lopez's curls were at their tightest when she attended the 1995 premiere of her film "Money Train" in a simple champagne-colored halter-dress.
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Jennifer Lopez donned a strapless blush Versace gown with a corset-style bodice at the 2002 Oscars. The dress may be timeless, but her enormous bouffant-style hairdo definitely is not!
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Jennifer Lopez donned this truly terrible dress with an asymmetrical skirt at the 2004 MTV Video Music Awards. She completed her look with a big hat and shoulder-skimming chandelier earrings.
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Jennifer Lopez looked elegant but matronly in a sleeveless, pearl-adorned dress at the 2006 Toronto Film Festival.
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Jennifer Lopez paired a shiny silver skirt with a pale gray turtleneck that she wore belted at the waist at the 2005 premiere of "An Unfinished Life."
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Jennifer Lopez rocked a slinky white-and-silver gown with midriff cut-outs at the 2004 premiere of "Shall We Dance?"
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Jennifer Lopez topped many best-dressed lists in this iconic Valentino number at the 2003 Oscars.
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White-hot, once again! Jennifer Lopez wore a strapless white cocktail dress with lace-up cut-outs on the sides at the 1998 GQ Men of the Year Awards.
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Jennifer Lopez played it safe at the 2006 Latin Grammy Awards in a dramatic black gown with a cinched bodice and a voluminous skirt with a ruffled hemline.
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Jennifer Lopez looked flawless in a pale pink one-shoulder Versace gown that fit her link a glove at the 2006 Met Gala.
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Jennifer Lopez looked glamorous in an olive Rita Watnick gown at the 2006 Oscars.
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Jennifer Lopez was simply divine in a timeless white gown with flowing three-quarter sleeves at the 2006 ALMA Awards.
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Jennifer Lopez wore this unforgettable look — a deep brown Gucci gown with a plunging neckline — at the 2003 premiere of "Gigli."
