Jennifer Lopez's Style Evolution, From 1998 to 2020

WireImage Jennifer Lopez Once upon a time, Jennifer Lopez rocked velour sweatsuits and leopard print. See the star's style evolution from Jenny from the block to an American fashion idol. First up: who's that girl? That's what millions said in 1994 when Lopez was first spotted on the Los Angeles music scene fully embracing her '90s look. Who doesn't love those wild, natural curls?

WireImage On Feb. 28, 1998, at the 17th Annual CFDA Awards an event celebrating another style icon, Elizabeth Taylor Lopez began to reveal her chic fashion flair in a sheer gown.

WireImage The Bronx singer started to push her style envelope, rocking a gold sequined dress at the 41st Annual Grammy Awards on Feb. 24, 1999.

WireImage J.Lo left less to the imagination in this plunging gown she wore to the VH1/Vogue Fashion Awards on Dec. 5, 1999. The dress stood out as Jenny's most jaw-dropping ensemble to date. Until...

WireImage Jaws dropped when Lopez hit the red carpet at the 42nd Annual Grammy Awards on Feb. 23, 2000, wearing the famous Versace gown that remains her boldest and most iconic look. The singer may not have taken home any awards that night, but it's easy to see why this is one of her most winning looks ever.

WireImage Lopez tipped her hat to her hip-hop roots when she showed up to the MTV Video Music Awards on Sept. 7, 2000, in this midriff-baring monochrome ensemble, matching then-boyfriend Sean "Puff Daddy" Combs to a T.

Lee Celano/AFP/Getty Images By now, Jennifer was a celebrated A-list actress as well as a chart-topping singer. Here, she's seen posing for photographers at the Shrine Auditorium during the 73rd Academy Awards in Los Angeles on March 25, 2001. At first, the Chanel haute couture gown appeared more demure than her previous ensembles, but the flashbulbs revealed a sexy surprise underneath the completely sheer top.

Getty Images Isn't she pretty in pink? Keeping her couture look hot (but a bit more PG-rated), Lopez attended the 74th Annual Academy Awards on March 24, 2002, in a gorgeous rose-colored Versace gown and glam curls.

WireImage Of course, she can still do casual and look just as fab: J.Lo's velour suit, complete with large gold hoop earrings, turned heads at MTV's TRL on May 22, 2002.

FilmMagic Halloween came early for Jen on October 29, 2003, as she showed up to the Dolce & Gabbana launch party at Bergdorf Goodman in NYC rocking a bandana, blue gown, and fur-trimmed coat. She earned fewer rewards for this fashion risk.

WireImage Jennifer quickly bounced back when she arrived at the Costume Institute Gala on April 26, 2004, wearing a decadent black Dolce & Gabbana gown.

FilmMagic Lopez showed up to the launch of her new album Rebirth at the Virgin Megastore in Times Square on March 1, 2005, in a fringed poncho, which hasn't totally aged well, but was trendy enough look at the time.

WireImage Once again, J. Lo recovered from a major fashion flop with a stunning high-glamor ensemble. She arrived at the El Cantante premiere at the Museo de Arte in San Juan, Puerto Rico, on July 23, 2007, looking like a true Hollywood star. We love how the sculpted, ruched evening gown was polished off with a pair of chandelier earrings, and a dramatic pulled-back 'do.

WireImage Singer, dancer, actress...designer! Lopez became a quadruple threat when her "Just Sweet" collection was launched during Mercedes-Benz Fashion Week. Here, she's seen strutting down the runway on Sept. 11, 2007, wearing the newly-launched line.

WireImage J.Lo showed up to the 66th Annual Golden Globe Awards on Jan. 11, 2009 looking like a Greek goddess. Dripping gold in a dazzling Marchesa gown, Lopez turned every head with her look, accented by Lorraine Schwartz jewels.

Getty Images for DCP Ms. Lopez had us flipping as she glowed in a pale pink feathered mini dress, seen here backstage at the 2009 American Music Awards on Nov. 22, 2009.

WireImage The Latina diva looked fabulous at the 2010 Vanity Fair Oscar Party in West Hollywood, wearing a dramatic Gucci gown festooned with an ostrich feather shoulder and side cutout.

WireImage Lopez stepped out at the World Music Awards 2010 on May 18, 2010 in Monte Carlo, Monaco, in a leopard gown that successfully incorporated both her street style and red carpet edge.

FilmMagic J.Lo stunned in all the right ways when she arrived at the Alexander McQueen: Savage Beauty Costume Institute Gala at The Metropolitan Museum of Art on May 2, 2011, in her striking red Gucci keyhole gown with floral shrug.

WireImage The now-42-year-old singer performed at the American Music Awards at L.A.'s Nokia Theater on Nov. 20, 2011, in a dramatic Swarovski-studded catsuit that showed off her incredible figure. Meow!

WireImage At the 2011 American Music Awards, Lopez stopped hearts on the red carpet in a beaded, form-fitting black-lace gown.

Michael Buckner/Getty Images The singer-actress walked the 2012 Oscars red carpet in a plunging Zuhair Murad gown. The dress was custom-made for J.Lo and echoed a favorite fashion motif -- nude fabrics with a decolletage-baring neckline.

Lester Cohen/WireImage In 2012, Lopez showed up to an event in a Lanvin dress with a Swarovski crystal snake wrapped around the neck that winded down the left side of the body. The dress fit J.Lo's high fashion tastes: not only was it covered in crystals, but the frock had a staggering $8,000 price tag.

Andreas Rentz/Getty Images 2012 must have been the year of Lanvin for J.Lo because at the 21st UNESCO Charity Gala, she kept things classy in a one-shoulder Chantilly lace Lanvin gown with a velvet sash.

Kevin Winter/Getty Images When you're Jennifer Lopez, a simple dress won't do when receiving a star on the Hollywood Walk of Fame. J.Lo wore a Dior ballgown, Brian Atwood shoes, a Valentino bag, and H. Stern earrings.

Kris Connor/Getty Images Ready to show a little skin at the 2013 Human Rights Campaign National Dinner, Jennifer wore a gown from one of her top choice designers (Zuhair Murad), which she accessorized with Brian Atwood shoes, a Swarovski bag, and Neil Lane jewels. Not quite the typical pantsuit those politicians in D.C. are accustomed to.

Christopher Polk/Billboard Awards 2014/Getty Images for DCP To accept her icon award at the 2014 Billboard Music Awards, Lopez walked the carpet in a sheer, low-cut, high-slit ruby Donna Karan dress. Icon, indeed!

Misha Vladimirskiy / State Farm For her return to the Bronx in 2014, Jenny from the block danced on her home stage in a pantless leotard reminiscent of her iconic 2000 Grammy Awards dress.

Alexander Tamargo/WireImage The singer bared her long legs in this colorful (and very Miami-appropriate) ensemble for a performance at the iHeartRadio Ultimate Pool Party on June 28, 2014, in Miami Beach, Fla.

Steve Granitz/WireImage At the 2014 MTV Video Music Awards in Inglewood, Calif., Lopez kept things sleek on the red carpet in a revealing silver gown by Charbel Zoe.

Frazer Harrison/Getty Images for CBS Radio Inc. J.Lo stunned in a two-piece ensemble by Celia K, which she accessorized with knee-high gladiator boots by Sophia Webster, during her performance at CBS Radio's We Can Survive benefit at the Hollywood Bowl on Oct. 24, 2014, in Los Angeles.

Gregg DeGuire/WireImage Lopez went neutral in a sultry Reem Acra bandage dress on the red carpet at the 2014 American Music Awards on Nov. 23, 2014, in Los Angeles.

Pascal Le Segretain/Getty Images Jennifer Lopez attended the 2015 Vanity Fair Oscar Party on Feb. 22, 2015, in Beverly Hills working a totally sheer Zuhair Murad Couture dress.

Jason Merritt/KCA2015/Getty Images J.Lo sported a mini-dress with a twist some serious lacy cutouts by Roberto Cavalli with matching Jimmy Choo stilettos at the Nickelodeon's Kids' Choice Awards on March 28, 2015, in Inglewood, Calif.

George Pimentel/WireImage The red-carpet diva looked fierce in her opulent, dragon-inspired Versace gown at the China: Through The Looking Glass-themed Met Costume Institute Gala on May 4, 2015, in New York City.

Axelle/Bauer-Griffin/FilmMagic Lopez put yet another spin on sheer in a stomach-baring Charbel Zoe Couture gown at the 2015 Billboard Music Awards on May 17, 2015, in Las Vegas.

D Dipasupil/FilmMagic Jennifer opted for a more traditional red-carpet look for the 2015 Tony Awards on June 7, 2015, in New York City, wearing a strapless, navy Valentino with sequin embellishments.

Rodrigo Varela/WireImage During the 2016 Latin Grammys, Lopez showed simplicity and elegance in this mini.

Trae Patton/NBC/NBCU Photo Bank via Getty Images Jennifer Lopez stunned at the 73rd Annual Golden Globe Awards in a stunning (and fairly conservative) yellow dress from Giambattista Valli.

Denise Truscello/WireImage Jennifer Lopez left little to the imagination in this leotard for her All I Have residency at the AXIS at Planet Hollywood Resort & Casino.

Neilson Barnard/Getty Images Here, Jennifer Lopez threw it back to the ’60s with a sky blue gown from the Spring 2017 Valentino couture collection.

Aaron Davidson/WireImage For the 2017 Billboard Latin Music Awards red carpet, J.Lo brought her usual glam in a shiny Julien MacDonald dress.

John Shearer/WireImage For the 2017 Grammys, Lopez wore a pretty lilac gown from Ralph & Russo's Spring 2017 Orchid Collection.

John Shearer/Getty Images for The Hollywood Reporter Lopez appeared at the 2018 Met Gala in an elaborate Olivier Rousteing gown detailed with blue, gold, and red jewels.

Axelle/Bauer-Griffin/FilmMagic Jennifer Lopez arrived at the 2019 Vanity Fair Oscar Party wearing a strapless gown with blue, purple and black sparkles, designed by Zuhair Murad. The dress was part of Murad's Couture Spring/Summer 2019 collection.

Dia Dipasupil/FilmMagic JLo nailed the Celebrating Camp: Notes on Fashion theme at 2019’s Met Gala in New York City, rocking an iridescent Versace gown with a high slit and Low-V neck. She completed the look with a matching headpiece resembling a wig.

Stephen Lovekin/Shutterstock Lopez commanded attention on the 2019 CFDA Fashion Awards red carpet at the Brooklyn Museum, posing in a sunset orange co-ord, pairing her cropped turtleneck top with silky trousers that cascaded into a long train behind her. Her sleek pony added to the chic factor.

John Parra/Getty Images for STXfilms / Alexander Wang Lopez kept it urban-glam at the Hustlers premiere in NYC, opting for a strapless grey jumpsuit and pointed-toe pumps. She gave us "Jenny from the Block" vibes with her nameplate necklace and half-up hairdo.

MIGUEL MEDINA/AFP via Getty Images 19 years later, JLo slipped back into her iconic Grammys gown, looking like not a day had passed when she strutted down the Versace Women’s Spring/Summer 2020 runway in Milan. The updated version of the dress featured short sleeves and a new silver buckle.

Steve Granitz/WireImage The golden goddess rocked a sleek metallic gown at the 2019 Academy Of Motion Picture Arts And Sciences' 11th Annual Governors Awards, which she paired with simple jewelry and clutch. The look, however, was anything but boring, thanks to the braided bun atop her head.

Axelle/Bauer-Griffin/FilmMagic Lopez’s red carpet look at the 77th Annual Golden Globes in Los Angeles made a statement. Her white gown was tied together with a large green and gold bow, paired with contrasting silver jewelry. Once more, she opted for a sleek bun.

Steve Granitz/WireImage Lopez was a vision of class at the 26th annual Screen Actors Guild Awards, with an off-the-shoulder black gown that left her toned back bare. She switched up her signature high bun for a low one, with her front pieces of hair pulled out for an effortlessly glam look.

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