Jennifer Lopez’s Incredible Fashion Evolution: Photos

When Jennifer Lopez hits a red carpet, all eyes and camera lenses are focused on her — but it wasn’t always that way. She, of course, was destined for Hollywood superstardom, but her fashion had to catch up with her star wattage and talent. Let’s just say it’s been a journey… but in a moment, one designer and one dress changed the game for J.Lo, and a fashion icon was born.

On Feb. 23, 2000, Lopez stepped on the red carpet in a green Versace silk-chiffon gown that was so revolutionary, Google created their “Image Search” tab because “it was the most popular search query we had ever seen,” according to former Google CEO Eric Schmidt. The world paid attention, and “Jenny From the Block” knew there was no going back from the iconic dress that even boasts its own Wikipedia entry.

While she would describe the plunging green dress as her “most famous” fashion moment, she told Vogue that her favorite dress doesn’t exist, “it’s too hard to choose.” Her preferred daily style is “kind of relaxed and tomboyish, but with a little bit of sexy in it.” Yet when she steps in front of the cameras — it’s all glam, baby. And fashion designers trip over themselves trying to get Lopez to wear their creations, from Marchesa to Gucci, she made everyone pay attention to her gorgeous curves.

And while her style grew from following the trends to creating the trends, Lopez has always made an impression. Take a look at her fashion evolution from 1996-2023, 27 years of J.Lo dazzling her fans with her stunning ensembles.

1996: ‘Selena’ Press Conference

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J.Lo was all business in a pale pink skirt suit at the 1996 press conference for her breakthrough role in Selena.
1997: ‘Anaconda’ Premiere

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She was ahead of her time in working those curves in body-con dresses, and we wouldn’t mind if those curls made a comeback.
1998: MTV Movie Awards

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This metallic outfit screams late-90s fashion with the silver kerchief top and long skirt paired with butterfly clips in her hair. J.Lo was trendy, but she was still finding her style here.
1998: Grammy Awards

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This was the year that Lopez’s sleek style began to form with the chic gold dress that shimmered from every angle and showed off her gorgeous dancer legs.
1999: Billboard Music Awards

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Minus the chunky-heeled boots, Lopez could easily rock this edgy style from 24 years ago at the Billboard Music Awards.
2000: Grammy Awards Photoshoot

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Lopez joined other Grammy-nominated artists for a photoshoot in 2000, so she wanted a vibe that showed she belonged in the music industry while still showing she meant business.
2000: Grammy Awards

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The game-changing dress that cemented J.Lo as a red-carpet superstar — she became a hot commodity among fashion designers, thanks to Versace’s daring creation.
2000: MTV VMAs

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This look was from her Puff Daddy dating era, and this outfit (with a Sean John crop top) perfectly reflected the synergy of their relationship and their music styles.
2001: Super Bowl

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J.Lo looked cute and country with her statement belt bedazzled with rhinestones. She would return to the Super Bowl 19 years later as the halftime show headliner with Shakira.
2001: Oscars

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Freeing the nipple in 2023 isn’t that big of a deal, but in 2001, it was downright shocking, especially at the Oscars. But this Chanel gown was so soft and pretty that she was one of the night’s best-dressed stars.
2002: Oscars

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Lopez was pretty in pink in this structured Versace gown with bombshell hair that gave off a 1960s vibe.
2003: Oscars

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Nobody could forget this epic red-carpet night because this was the Bennifer 1.0 era and the start of the J.Lo glow (Ben Affleck had a matching spray tan, too). The mint-green gown from Valentino is still one of her most memorable looks.
2006: MTV VMAs

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J.Lo loves a 1960s moment and she nailed this sultry look in a Biba mini dress and headscarf.
2009: Golden Globe Awards

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She looked like a Golden Globe statuette, opting for another plunging neckline in a very sophisticated design from Marchesa.
2015: Met Gala

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Lopez ditched the undergarments and invested in double-sided tape for her very revealing red dragon Versace gown. The theme of the 2015 Met Gala was “China: Through The Looking Glass” — and she nailed it!
2017: Grammy Awards

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J.Lo took an unexpectedly soft and pretty turn in a Ralph & Russo lavender gown from their Spring 2017 Couture collection.
2018: ‘Second Act’ Movie Premiere

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She went for the drama at the Second Act movie premiere with a high-low hemline gown by Giambattista Valli.
2019: Met Gala

Image Credit: Dimitrios Kambouris/Getty Images for The Met Museum/Vogue.

This sparkling Versace dress had it all: cleavage, a plunging V-neckline, and a high-cut slit.
2020: Super Bowl Press Conference

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J.Lo found a sleek and stylish way to rock her Super Bowl press conference with an on-trend crop top and high-waisted pants in all-white. She knew all eyes were on her, and she was ready!
2021: Venice Film Festival

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The moment everyone was waiting for the debut of Bennifer 2.0 on the red carpet. The Georges Hobeika couture dress was perfectly styled with a dash of diamonds and a revealing neckline that was just as exciting as seeing Lopez and Affleck back together again.
2023: Grammy Awards

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Lopez is in her most confident era yet; you can tell she looks and feels good in this stunning rhinestone-covered navy Gucci gown. It shows off every gorgeous angle and proves what a superstar she is.