Although we've spilled a lot of ink talking about '90s-era celebrities who shy away from taking fashion risks, we'd be remiss if we overlooked a daring style icon who rose to prominence during the decade, someone who isn't one to play it safe. We're of course referring to Jennifer Lopez. The style muse has been stepping onto the red carpet in outfits that elicit audible gasps ever since she donned that now-iconic, barely there green Versace gown in 2000 (you know the one).
Ahead, we culled through Getty's archives to bring you Lopez's most viral outfits of all time. Spanning the shockingly sheer Chanel ball gown she wore to the 73rd Annual Academy Awards in 2001 to the glittering naked dress she donned at the 2015 Vanity Fair Oscar Party to the jaw-dropping crystal-encrusted crop top she sported at the 2019 CFDA Awards, these are without a doubt Lopez's most talked about red carpet moments to date. Scroll on to relive all of J.Lo's most memorable fashion moments from 1998 to 2019.
WHAT: 17th Annual CFDA Awards
STYLE NOTES: Lopez stunned in a sheer, sparkly black dress, showing her affinity for naked dresses early on.
WHAT: 55th Annual Golden Globe Awards
STYLE NOTES: She bared her toned abs when she walked the red carpet in this color-blocked cutout gown at the Golden Globes.
WHAT: 7th Annual MTV Movie Awards
STYLE NOTES: Lopez was the epitome of the '90s fashion in a sparkly halter top, low-rise leather skirt, and rhinestone barrettes.
WHAT: 1998 MTV Video Awards
STYLE NOTES: Just the first of many statement-making hats Lopez has worn on the red carpet.
WHAT: 42nd Grammy Awards
WEAR: Versace dress
STYLE NOTES: This plunging Versace dress solidified Lopez's status as a risk-taking style icon.
WHAT: 2000 MTV Video Music Awards
WEAR: Sean John crop top and jeans
STYLE NOTES: Lopez donned a midriff-baring all-white ensemble to the 2000 VMAs, complete with, yes, belly button art.
WHAT: 73rd Annual Academy Awards
WEAR: Chanel gown
STYLE NOTES: The style icon turned heads in this sheer Chanel ball gown at the 73rd Annual Academy Awards.
WHAT: 75th Annual Academy Awards
WEAR: Valentino gown; Harry Winston jewelry
STYLE NOTES: A marked departure from her revealing red carpet looks, this one-shoulder gown was a stunner.
WHAT: 53rd Annual Grammy Awards
WEAR: Emilio Pucci minidress; Christian Louboutin heels
STYLE NOTES: Lopez did the most (in the best possible way) in a sparkling mini dress, studded heels, and a crystal encrusted clutch.
WHAT: 70th Annual Golden Globe Awards
WEAR: Zuhair Murad gown
STYLE NOTES: This sheer lace gown was a harbinger of many naked dresses to come in Lopez's fashion future.
WHAT: 55th Annual Grammy Awards
WEAR: Anthony Vaccarello gown
STYLE NOTES: J.Lo proved that black doesn't have to be boring with this high-slit, one-shoulder gown.
WHAT: 2014 Billboard Music Awards
WEAR: Donna Karan bodysuit
STYLE NOTES: A plunging neckline and leg-baring silhouette made this red carpet look one to remember.
WHAT: 2015 Vanity Fair Oscar Party
WEAR: Zuhair Murad
STYLE NOTES: J.Lo stepped out in yet another naked dress for the 2015 Vanity Fair Oscar Party.
WHAT: 17th Annual Latin Grammy Awards
WEAR: Zuhair Murad Couture jumpsuit
STYLE NOTES: Lopez wowed at the Latin Grammys in a sheer jumpsuit with strategically placed embellishments.
WHAT: 59th Grammy Awards
WEAR: Ralph & Russo gown; Christian Louboutin heels
STYLE NOTES: Who could forget this pink confection complete with a plunging neckline and high slit up to there?
WHAT: 2017 Billboard Latin Music Awards
WEAR: Julien MacDonald gown
STYLE NOTES: This J.Lo look checked all the boxes. High slit? Check. Plunging neckline? Check. Sultry cutouts? Check.
WHAT: 61st Annual Grammy Awards
WEAR: Ralph & Russo column gown
STYLE NOTES: The style icon made headlines after sporting one of her signature accessories on the Grammy's red carpet.
WHAT: 2019 Met Gala
WEAR: Versace dress; Judith Leiber clutch; Harry Winston Jewelry
STYLE NOTES: Lopez brought the drama to the 2019 Met Gala in a beaded Versace gown and matching headdress.
WHAT: 2019 CFDA Awards
WEAR: Ralph Lauren top and skirt
STYLE NOTES: Lopez made our collective jaws drop when she showed off her abs and wore a sparkly crop top glittering with over 43,200 crystals.
Up next, three items Jennifer Lopez wears instead of jeans.
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J.Lo Just Debuted a New Way to Wear This "Boring" Blazer Trend That Feels So 2025BRB, I'm adding one to my cart.
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J.Lo Wore the Elegant Trend That Makes Every Outfit Look Like It Came From an Audrey Hepburn MovieFrom Charade to Breakfast at Tiffany's.
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J.Lo Somehow Just Made Denim Feel Like a Totally Normal Choice for a 5-Hour FlightNow, I want to wear jeans on an airplane.
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J.Lo Just Wore This Highly Controversial Trend in the Most Elegant Way PossibleShe can do anything.
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J.Lo Just Wore the Pants Trend London Women Wear Instead of Skinny JeansThe perfect alternative.
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J.Lo Wore the Brand-New Uggs That'll Go Viral and Sell Out By December 1—GuaranteedDon't say I didn't warn you.
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After Seeing J.Lo's Outfit, I Placed a J.Crew Order for This Elegant Basic ImmediatelyI kid you not.
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I Thought This Heel Trend Was Dated, But These Celebrity Outfits Just Changed My MindConsider me convinced.
