Jennifer Lopez has been walking red carpets for well over 20 years, and her style history is rich. Wonderwall.com is looking back at Jenny from the Block's wildest retro fashion moments — including some wonderfully outdated looks. First up? The ensemble she wore to the 1998 MTV Movie Awards: a slinky silver halter top with a leather maxi-skirt. Our favorite part of this look, though? The two blinged-out berets she wore in her hair. It doesn't get more '90s than that!
Keep reading for more of J.Lo's fashion history…
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Jennifer Lopez rocked a puzzling look — creamy trousers, a white bralette and an oversized cream blazer all topped off with a cowboy hat — during the 1998 MTV Video Music Awards.
When she dated Ben Affleck (for the first time), Jennifer Lopez's style matured into something more Hollywood glam. To support Ben at his "Daredevil" premiere, she kept her look simple with a black strapless gown featuring a colorful band along the top. She also wore a lot of bronzer at the time.
In 1998 when she attended the premiere of her film "Out of Sight," Jennifer Lopez opted for a conservative — and very shiny — look with this champagne-colored dress, low pumps and matching bolero jacket.
Jennifer Lopez rocked this look at the 2000 MTV Video Music Awards outfit. It's one of her most famous ensembles ever. J.Lo got in touch with her Bronx roots in white flared jeans, a matching Sean John crop top and a bedazzled white bandana headband.
Jennifer Lopez's most memorable fashion choice of all time? The deep-V green palm-print Versace dress the then-30-year-old star wore to the Grammys in 2000. It might be retro, but it still holds up (on her, at least!) today.
Jennifer Lopez embraced a va-va-voom moment in 2005 in this black halter gown with a train and a big updo.
Jennifer Lopez wore a blush-hued tiered and ruffled gown by Vera Wang at the 2002 premiere of "Maid in Manhattan."
At the 1997 Oscars, Jennifer Lopez — who was still with first husband Ojani Noa at the time — opted for a mature look in a sparkly cap-sleeved gown, big, barrel-curled hair and dark lipstick.
Jennifer Lopez's curls were at their tightest in 1995 when she attended the premiere of her film "Money Train" in a very basic champagne-colored halter gown and some open-toed heels.
For her "On the 6" album launch party in 1999, Jennifer Lopez showed off her enviable abs in a matching white skirt and crop top ensemble with pale frosted makeup.
For the Academy Awards in 2002, Jennifer Lopez wore a blush pink strapless bustier gown that now seems like a classic. Her enormous bouffant-style hairdo, however, missed the mark then and now.
At the 2003 London premiere of her movie "Maid in Manhattan," Jennifer Lopez wore a muted brown mermaid-style dress that still holds up today. The white fur bolero jacket she added, however, does not.
In 2005 for the premiere of "An Unfinished Life," Jennifer Lopez opted for a monochromatic silver look anchored by a shiny skirt and a pale gray turtleneck that she belted at the waist.
Jennifer Lopez's curly hair, plain makeup takes us back in time to the 1998 premiere of "The Man in the Iron Mask." Could you imagine her in a strapless zig-zag patterned dress like this today?!
Jennifer Lopez played it safe at a 1997 fashion benefit in a black leather-look gown that was, sadly, incredibly ill-fitting.
Jennifer Lopez looked a little eccentric at a Dolce & Gabbana party in 2003 in a pink-hued headscarf and a champagne-colored jacquard coat that she wore over a blue dress.
At the American Music Awards in 2001, Jennifer Lopez wore a flimsy little dress in her favorite color — white — along with a giant floppy hat.
Jennifer Lopez combined a few retro faves back in 1999 when she showed up at the Met Gala, which had a "Rock Style" theme that year, wearing this very glitzy low-cut champagne frock and pale eyeshadow.
Early-2000s Jennifer Lopez loved a hat for a red carpet moment. At the 2001 MTV Video Music Awards, she paired a light brown floppy hat with a sheer animal-print peasant top, black booty shorts and black thigh-high leather boots.
Jennifer Lopez was literally glowing at the 2004 Golden Globes in a serious spray tan that matched her plunging orange gown.
Jennifer Lopez was minty fresh at the Academy Awards in 2003 in a flowing one-shoulder dress with flowery edges and matching pale green eye makeup that aged the look instantly.
White-hot, once again! At the GQ Men of the Year Awards in 1998, Jennifer Lopez wore a sexy, strapless white cocktail dress with lace-up cut-outs on the sides.
For the premiere of her infamous movie "Gigli," Jennifer Lopez wore her hair in a stiff, dramatic updo that showed off her chandelier earrings and a brown gown that gave the illusion her bodice was bursting at the seams.
Jennifer Lopez was all about Miami when the MTV Video Music Awards were held there in 2004. The singer wore a big brown hat with her hair pulled back and oversized chandelier earrings along with a funky gold and bronze dress with a red ruffled insert.
At the 1999 Grammys, Jennifer Lopez was pure glitz in a bright yellow sparkly minidress with pin-straight hair that was all the rage at the time.
Pretty in pink! At the 2000 ALMA Awards, Jennifer Lopez chose a raspberry-colored halter dress with a half-up, half-down hairstyle.
For the 1997 Independent Spirit Awards, Jennifer Lopez covered up in a matronly floral-embroidered dress that she wore with her hair piled up on her head.
Jennifer Lopez wore her hair in tight curls and chose a super-sexy albeit risky outfit for the 2002 MTV Video Music Awards: a blazer-inspired top that showed off her tanned chest with a matching black curve-hugging skirt.
A very brunette Jennifer Lopez looked elegant but matronly in a cream-colored dress with textured embellishments during the 2006 Toronto Film Festival.
Jennifer Lopez played it safe at the Latin Grammys back in 2006 in a dramatic black gown that was as conservative as it was voluminous.
Jennifer Lopez experimented with a new color, for her, in 2006 when she wore a pea green gown that hugged all the right places paired with statement diamond earrings and a matching necklace for the Vanity Fair Oscar Party.
Jennifer Lopez attended the 2006 Met Gala in a Grecian-style gown wrapped tightly at her waist.
Jennifer Lopez rocked a serious spray tan with a slinky white-and-silver gown that featured cut-outs along her ribcage at the 2004 premiere of "Shall We Dance."
In 2006 for the ALMA Awards, Jennifer Lopez wore a blazing-hot white dress with fluttery sleeves and a deep V-neck that actually holds up today.