Photo by Ke.Mazur/WireImage, Scott Gries/ImageDirect and Pool LE FLOCH/TRAVERS/Gamma-Rapho via Getty Images

7 of Jennifer Lopez's most iconic outfits

J.Lo's the ultimate popstar and fashion icon — whether wearing Versace, Tom Ford or Timbs — but she’ll always be Jenny from the block.

by Zoë Kendall
04 June 2021, 7:00am

Photo by Ke.Mazur/WireImage, Scott Gries/ImageDirect and Pool LE FLOCH/TRAVERS/Gamma-Rapho via Getty Images

When it comes to Jennifer Lopez the term “triple-threat” feels like an understatement. Since starting out as a backup dancer and choreographer, the multi-hyphenate entertainer has made an indelible mark on the realms of cinema, music, dance and beyond. Over the course of her near four-decade spanning career, the star has garnered critical acclaim for her roles in blockbusters like Selena and Hustlers, topped the charts with her Latin pop music, and has been dubbed one of pop music’s greatest dancers. Beyond these accolades, J.Lo has also earned her place as a cultural icon, as well. Her high-profile relationship with actor Ben Affleck coined the first portmanteau celebrity couple name, Bennifer. And who could forget her buzz-worthy Versace gown — you know, the one that basically invented Google Image Search. In fact, Jen’s predilection for risk-taking fashion — from Tom Ford’s sexy Gucci dresses to heeled Timbs — has made the star into a veritable fashion icon, even earning her the CFDA’s coveted Fashion Icon award in 2019. Here, we honour J.Lo’s cultural and sartorial legacy, ourselves, by revisiting the star’s most iconic outfits, ever.

jennifer lopez in a sheer 90s black gown at the cfda awards
Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images

At the CFDA Awards, 1998

Jennifer Lopez has always had a penchant for the naked dress — even since the early days of her career. While she began acting in the late 80s, taking on bit roles in film and television, Jennifer’s breakthrough moment arrived when she played Tejano music star Selena in the eponymous 1997 biopic. J.Lo’s performance earned the praises of industry critics and the film sweeped that year’s ALMA Awards, with Jennifer winning the award for Outstanding Actress in a Feature Film. Here, to the CFDA Awards, a year after playing in her star-making role, J.Lo wears the first of many naked dresses to come: a sparkly — and very sheer — fitted slip dress. Over 20 years after her turn on the CFDA red carpet, the star was named the recipient of the fashion council’s Fashion Icon award in 2019.

jennifer lopez wearing a white baby tee and skirt at the on the 6 release party
Photo by Ke.Mazur/WireImage

At her On the 6 album release party, 1999

In 1998, J.Lo transitioned from acting to singing with the release of her debut album On The 6. With this career transition also came a style transition for the newly-minted musician. About J.Lo’s On The 6 look, the singer’s then-stylist, Andrea Lieberman, told Vogue, “She is not one person, and she has depth and richness.” Andrea translated J.Lo’s multitudinous persona — triple threat that she is — into an ultra-plush, proto-athleisure look that took in staple separates in daring cuts and dazzling fabrications. Here, to the album’s release party, J.Lo wears just that: a white jersey two-piece set with a backless, cropped T-shirt. This particular ensemble set the mood for the singer’s On The 6 era, and tied into her album cover look (long sleeve tee and lamé hot pants), as well as the myriad luxe-minimalist looks (Ralph Lauren cargo pants and spangled Versace mini) worn throughout her debut music video.

p diddy and jennifer lopez embracing at the vh1/vogue fashion awards
Photo by Ke.Mazur/WireImage

At the VH1/Vogue Fashion Awards, 1999

One year before J.Lo (literally) broke the Internet with one Versace gown, the singer showed her predilection for a plunging neckline at the now-discontinued VH1/Vogue Fashion Awards in 1999. In keeping with the laid-back glam look of her On The 6 era, J.Lo wore a crystal-encrusted henley-style dress designed by Tom Ford for Gucci. This wasn’t the first time the star wore the American designer’s ultra-sexy designs for the Italian house. To a 1997 AIDS benefit, hosted by the designer, himself, J.Lo donned a strappy, backless lamé gown from the brand’s SS97 collection.

jennifer lopez in a green deep v versace dress
Photo by Scott Gries/ImageDirect

At the Grammy Awards, 2000

Did you know that her stylist initially didn’t want J.Lo to wear that Versace gown? Andrea’s advice came on the basis that the now-iconic gown had already been worn that year by the Spice Girls’ Geri Halliwell, Sandra Bullock and even Donatella Versace. In other words, the look had been done already. Jennifer, however, was adamant. And her intuition paid off, leading to one of the most iconic fashion moments of the 21st century. Although the look had been seen before on the red carpet, J.Lo’s appearance in the near-impossible gown at the 2000 Grammys caused a huge buzz, namely for its plunging neckline. The following morning, Google was inundated with searches from those eager to see J.Lo in the dress. Not only was J.Lo’s dress a massive pop cultural moment, but a landmark moment for Google, leading the search engine giant to launch its Image Search. Years later, J.Lo played it off to Vogue, admitting, “I didn’t think [the dress] was all that risqué, to be honest.” However, the look was so iconic that Donatella invited J.Lo to don a reimagined version of the headline-making gown on the house’s SS20 runway. It’s not every day a dress earns its own Wikipedia entry.

p diddy with his arm around jennifer lopez on the mtv vmas red carpet
Photo credit should read HENNY RAY ABRAMS/AFP via Getty Images

With Puff Daddy at the MTV VMAs, 2000

Before Bennifer, there was Puff Daddy. J.Lo had an on-again, off-again relationship with the rapper and record producer from 1999 to 2001. During their relationship, the duo worked together, Puffy producing tracks from On The 6 and Jennifer’s sophomore album J.Lo. Here, to the 2000 MTV VMAs, Jennifer commemorates their relationship sartorially, wearing a tank top from her beau’s fashion line, Sean John. The singer completed the iconic, monochromatic look with ultra low-rise jeans, nameplate necklace, crystal body art, bedazzled bandana and her signature hoop earrings.

“I’m Real (Remix)” music video, 2001

Does it get any more Y2K than a Juicy Couture tracksuit? Turns out, J.Lo had a hand in putting the iconic aughties loungewear brand on the map. While filming the music video to accompany the remix of 2001 single “I’m Real”, the then-unknown brand sent the star a set of its iconic sweatsuits to lounge around the set in. The singer loved the tracksuits so much, however, that she decided to don one of them on camera. J.Lo paired the pink hot-pantsed velour ensemble with her signature nameplate necklace, hoop earrings and adidas sneakers. “I shocked everyone when I decided to wear it! It seemed fitting since the song is called ‘I’m Real’, so I decided to be ME!!” the star wrote in an Instagram caption about the shoot.

“Jenny from the Block” music video, 2002

We know that J.Lo’s one to wear her love on her sleeve — or, literally, on the front of her Sean John tank top. In 2002, Jen moved beyond the bedazzled tee, memorializing her relationship with actor Ben Affleck in the music video for 2002 single “Jenny from the Block.” The iconic 00s couple (known as Bennifer) met on the set of critically panned comedy film Gigli. On top of becoming tabloid staples, the duo went on to collaborate on romantic drama Jersey Girl and the singer’s iconic “Jenny from the Block” clip. Poking fun at their relationship with the press, the video features the couple being papped on a yacht, dining on a terrace, filling up at the gas station, etc. While the pair’s coupling outfits are iconic in themselves (J.Lo in a pink bikini and Ben in camo cargo shorts), the singer’s most memorable “Jenny from the Block” fit arrives during one of the video’s dance breaks. Getting down in the midst of NYC traffic, Jen wears a mesh tank, pageboy cap, cargo pants and heeled Timberland boots. The massive outfit, which merges luxury with streetwear signifiers, doubles down on the song’s message. “I stayed grounded as the amounts roll in / I'm real, I thought I told you,” Jen sings on the second verse. Despite her stature as a fashion icon — whether wearing Versace, Tom Ford or Timbs — she’ll always be Jenny from the block.

Follow i-D on Instagram and TikTok for more fashion.

Jennifer Lopez
7 Iconic Outfits