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Jennifer Lopez’s Best Red Carpet Looks, Based On Risk Factor

A hat is her most popular accessory.
STYLECASTER | Jennifer Lopez Red Carpet Look
Getty Images.

Besides being one of the most in-demand performers of our generation, Jennifer Lopez is also the definition of a red carpet mainstay. She has appeared on countless red carpets over the course of her decades-long career—it’s nearly impossible to pick a favorite Jennifer Lopez red carpet look. And yes, I a including the green Versace dress that literally created Google Images in that statement. Fashion Twitter, don’t come for me! Each moment the singer has created on the carpet stands out because each look is created exclusively with statement pieces. From wide-brimmed hats to capri pants and sheer cut-outs, Jennifer Lopez has never been afraid to take a red carpet risk—and in my opinion, they always pay off. 

Between Jennifer Lopez’s multi-look wedding with Ben Affleck and their honeymoon, there’s been no shortage of outfit inspiration from the star over the past few years. Whether it’s a black-tie affair or just a trip to the gym, you can expect J-Lo to be wearing something fabulous (like her Birkin bag valued at over $100k). Jennifer Lopez recently most recently walked the red carpet for the premiere of her new Netflix film, The Mother which inspired the following red carpet roundup. 

Keep reading for some of the best Jennifer Lopez red carpet looks based on fashion risk-factor throughout the years.

STYLECASTER | Jennifer Lopez Red Carpet Look
Getty Images. Getty Images.

1. The 2000 Grammy Awards

This dress from the 42nd Annual Grammy Awards in 2000 was an easy choice for Jennifer Lopez’s most iconic red carpet look. The famous green Versace dress features a deep-v neckline and was a controversial pick for the time (though it’s just about as Y2K as an outfit can get). Jennifer Lopez re-wore the famous dress in 2021 on the Versace runway.

STYLECASTER | Jennifer Lopez Red Carpet Look
Getty Images.Getty Images.

2. The 2021 Met Gala, In America: A Lexicon Of Fashion

Jennifer Lopez leaned into the Western roots of designer Ralph Lauren for the 2021 Met Gala themed, “In America: A Lexicon of Fashion.” She wore a massive leather choker, belt and fur bag for the occasion but if there’s one accessory J-Lo loves, it’s a hat.

STYLECASTER | Jennifer Lopez Red Carpet Look
Getty Images.

3. The 2001 Academy Awards

Jennifer Lopez wore a stunning Chanel gown to the 2001 Academy Awards in Los Angeles. The look was classy and elegant with an off-the-shoulder top and full floor-length skirt. While the bottom of the gown was structured, the top was totally see-through which gave the look a risky edge. 

STYLECASTER | Jennifer Lopez Red Carpet Look
Getty Images.

4. The 1998 Golden Globe Awards

Jennifer Lopez made her Golden Globe Awards debut in a one-shoulder cut-out dress in 1998. While most celebrities opt for something that resembles a princess gown for this event, Lopez made a statement by wearing something sleek. TBH,I think most celebrities would gladly rock this look now. 

STYLECASTER | Jennifer Lopez Red Carpet Look
Getty Images.

5. The 2015 Met Gala, China: Through The Looking Glass

If Jennifer Lopez is wearing something ultra-sexy, you can bet it’s Versace. The singer wore a beaded red Versace gown to the 2015 Met Gala that featured strategically placed mesh side paneling.

STYLECASTER | Jennifer Lopez Red Carpet Look
Getty Images.

6. The 2004 Nickelodeon Kid’s Choice Awards

The Kid’s Choice Awards are always a more casual event which leads to some fun outfit choices. Jennifer Lopez went for a look that really played to the younger audience. She wore multiple hip trends including PVC heels, capri pants, a crop top, a sequin short-sleeve shrug, and of course, a knit beret. That’s about as risky as it gets.

STYLECASTER | Jennifer Lopez Red Carpet Look
Getty Images.

7. The 2019 “Hustlers” Premiere

Jennifer Lopez wore a bright shade of yellow to the Hustlers premiere in Ontario, Canada in 2019. The dress included the singer’s signature low-v cut in the front and also had a high leg slit up the middle.

STYLECASTER | Jennifer Lopez Red Carpet Look
Getty Images.

8. The 1998 MTV Movie Awards

If you had said this was a current photo based on the outfit, I’d believe you. J-Lo proves that fashion always comes back around in this chainmail halter top and leather pants—a risky style that has returned to mainstream fashion with a vengeance.

STYLECASTER | Jennifer Lopez Red Carpet Look
Getty Images.

9. 2023 “The Mother” Premiere

You know what they say, “Mother is mothering.” Jennifer Lopez gave a professional ensemble a sexy spin by pairing a bra top with a maxi skirt and trench-stye jacket at the 2023 premiere of her movie The Mother on Netflix.

STYLECASTER | Jennifer Lopez Red Carpet Look
Getty Images.

10. The 2006 Vanity Fair Oscars Party

Versace does it again! Jennifer Lopez took a new approach to her famous green Versace dress in this Old Hollywood style gown. The look was a chic choice for 2006 and would look just as great on a red carpet today.

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