If anyone should be considered a fashion trailblazer, it’s Jennifer Lopez. The multihyphenate – who turns fifty on July 24th – has been making bold sartorial choices since she first burst on the scene in the late ’90s. While her early must-have wardrobe items of crop tops and sheer naked dresses were super sexy, her most controversial fashion moment was at the Grammy Awards in 2000 wearing that unforgettable Versace gown.
“[She] uses clothes as a way to express confidence and power. Both designers and fans look forward to her fashion statements,” CFDA chairwoman Diane von Furstenberg said when the Love Don’t Cost A Thing singer was presented with the 2019 CFDA Fashion Icon Award.
While Jennifer’s signature red carpet style consists of go-to designers – Versace, Zuhair Murad and Armani – she’s been experimenting with a new look of late. Case in point: her dress and oversized wide-brimmed hat by Australian duo Ralph & Russo. To celebrate J.LO’s milestone fiftieth birthday we’re revisiting her twenty most memorable fashion moments over the last two decades. Scroll to discover Lopez’s style file from 1998 -2019…
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From her barely-there slip dress to deep red wine coloured lip, this is ’90s fashion at its best for the 17th Annual CFDA Awards 1998.
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The dress that changed everything: Lopez wearing Versace to the Grammy Awards in 2000.
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Lopez opted for a pale pink one-shoulder gown by Versace, over a decade on and it’s still a classic, marking the start of her transition to fully-fledged fashion star.
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A delicious berry hue, here J.Lo wears Gucci to the MET Gala in 2011.
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Cut-outs and sequins are a perfect fit for the singer at the 2014 MTV VMAs.
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Oozing old Hollywood glamour in Elie Saab at the Vanity Fair Oscars after-party 2015.
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In Versace at the Met Gala; China: Through The Looking Glass 2015.
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Looking like a bronze goddess at the 87th Annual Academy Awards 2015.
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Rocking a glittering jumpsuit like no other in Chabel Zoe at the Billboard Music Award 2015.
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In a stunning printed skirt for the One Voice: Somos Live! A Concert for Disaster Relief to help victims of the recent natural disasters in Mexico, the southern United States, Puerto Rico and the Caribbean.
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Putting her own twist on a classic silhouette in Reem Acra at the People’s Choice Awards 2017.
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At the SiriusXM’s Town Hall With The Cast Of ‘Second Act’ Hosted By Andy Cohen 2018.
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Making a case for bold citrus tones at a photocall for her latest flick, The Second Act in 2018.
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This bright fuchsia In Giambattista Valli dress is a dream. Not many people could pull this tiered gown off yet, the Second Act world premiere.
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Jennifer looks like a modern Cinderella in a flowy, blue Valentino gown at the 2017 Met Gala. That gorgeous sheer, flowing cape is the stuff of dreams.
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In Balmain at the Met Gala subverting tradition iconography for the night’s theme ‘Heavenly Bodies: Fashion & The Catholic Imagination’.
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In Versace at the Met Gala; Nailing this year’s theme ‘Camp: Notes on Fashion’ in May.
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Dazzling in a sequin Zuhair Murad dress at the Vanity Fair Oscar party 2019.
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In Tom Ford at the 91st Annual Academy Awards 2019.
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For this year’s Grammy’s Lopez opted for Australian designers Ralph & Russo – stealing the show in that glorious hat.
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Owning the stage in an asymmetric jumpsuit that’s become a hallmark of her It’s My Party world tour.
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In Ralph Lauren crop top and skirt from the designer’s Fall 1999 collection at the Fashion Icon Awards 2019.
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