Jennifer Lopez's Iconic Style Transformation In Photos

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Jennifer Lopez knows the importance of fashion. "Whether it's in a movie role or a music video that sets a trend for pop culture, or the red carpet, or transcending into a character, or giving you the confidence you need to perform in front of 20,000 people, fashion is about the powerful moments it creates that can inspire you and the world around you," she said at the 2019 CFDA Awards (via Vogue). The star was accepting the Fashion Icon Award, and her fearless approach to dressing has been her outlet time and time again amid the ups and downs of her decades in the spotlight.

Growing up in the Bronx, she was initially influenced by hip-hop-inspired looks, but her style transformation began when she started spending more time in Manhattan. The epicenter of pop culture exposed her to different aesthetics and cultures. "I did more of a downtown look, and I realized there was so much more out there. And that continued to grow as I entered the business," she explained. And, boy, has J-Lo had an iconic style transformation since then that we "Can't Get Enough" of.

When Jennifer Lopez's career truly started to take off in 1994, she was all about '90s trends. At the "Mi Vida Loca" premiere, she wore a beige, button-up dress with brown mules (one of the decade's hottest shoes). But her first premiere look was far from her favorite. "It was a kind of rayon blend polyester mini dress in a kind of sandy, poo-poo color with buttons," she told Vogue. She didn't confirm the designer and didn't keep the garment. J-Lo was also very much on trend at another event that year in a black, longline cardigan over what appeared to be a white satin playsuit with over-the-knee socks (another huge trend).

Her early dedication to trends made sense. She was in her mid-20s andstill finding her style. Though she'd found success as a Fly Girl dancer on "In Living Color," she was moving into acting via roles in the TV series "Second Chances," "South Central," and "Hotel Malibu." And wearing existing trends well was an easy way to get noticed.

Jennifer Lopez's sultry and glam fashion vibe started developing around 1998 when she began attending big events following the success of the movie "Selena." At the Golden Globes, she made a statement in a one-shoulder, muted yellow and purple cutout dress that showed her abs. The star was clearly on the radar of big designers, as the block-pattern dress was a Valentino creation (one of many looks she'd wear from the fashion house). We also saw her diva style at that year's CFDA Awards. J-Lo looked every inch the movie star in a sheer, strappy, black gown with embellishments down her front and a matching wrap. The piece was by one of the staples of Hollywood dressing, Halston, and she paired it with a classic red lip.

Lopez knew early on that movie star glam was her vibe. "I have the 'stardom glow.' See, I grew up watching real movie stars — Ava Gardner, Rita Hayworth, Marilyn Monroe. Glamorous women like those are why I wanted to get into the business," she told Movieline that year.

Jennifer Lopez began dating Sean "Diddy" Combs around 1999. Her relationship with the hip-hop mogul influenced her style (she told Vogue she took his fashion advice), as did her new music career, as she released her first album, "On the 6." At the MTV Music Awards, Lopez wore a gold, halter-neck crop top with chains and a black leather-look skirt that matched her then-boyfriend's leather-look pants. Lopez partially undid one zipper over her thigh for a sexy vibe intensified by her knee-high, black boots. The outfit's designer (or designers) are unknown, but the look proved she'd returned to her early love of hip-hop-inspired fashion.

We also saw that at the Met Gala when Lopez paired his look with one that gave off mob wife vibes. The look proved the star was ahead of her fashion time, as the mob wife aesthetic would be huge on TikTok two decades later. The star also wore a peach gown by an unspecified designer with an apricot fur-look jacket that demonstrated her penchant for statement pieces. Lopez told Vogue she met Donatella Versace, the woman behind the fashion house Versace, that night, which would steer her style journey for years to come.

In 2000, Jennifer Lopez made headlines for her notorious Grammys dress. She broke fashion rules and looked good doing it as the sheer, jungle-print, Versace gown was open past her navel and considered seriously risqué for the time. Lopez opened up about the gown on YouTube, recalling her stylist didn't want her to wear it because Donatella Versace already had. "I put on the green dress and I come out and [my manager] Benny [Medina] goes, 'That's it! That's it! Don't even talk about it, we're not, that's the dress, that's the dress.' And, of course, my stylist is mortified," J-Lo recalled. She told W that year she didn't anticipate the huge response, though her major red carpet moment was so searched for that it led to the invention of Google Image Search.

Lopez had also embraced Y2K fashion and reinvented herself as a pop star. At the MTV Europe Music Awards, she gave us PG-13 Hilary Duff in "The Lizzie McGuire Movie" vibes in her silver crop top, low-rise utility pants, and fur-lined, cropped jacket from an unknown designer. Lopez's plunging top confirmed her style had become more provocative. "Being sexy comes from being confident. People who are okay with themselves are the sexiest," she said at the time.

Jennifer Lopez was juggling a music career with an equally busy movie career by 2001. She appeared alongside Matthew McConaughey in the rom-com "The Wedding Planner" and had a wedding of her own, tying the knot with dancer Cris Judd. Her work and personal changes were reflected in her wardrobe.

We saw J-Lo's softer side at the Golden Globes via her wedding-inspired white, satin, one-shoulder gown. Her penchant for sparkle and shine was obvious via the shoulder embellishment, her huge stud earrings, chunky bracelet, and silver sandals. She also gave us loved-up, rom-com vibes in her matching pink two-piece while posing at an MTV VMAs afterparty with Jessica Simpson. Lopez added a sparkly pink headband that gave her a warm, youthful aesthetic in stark contrast to the sultrier looks we'd seen the year prior. She also sported lighter makeup for a more girly, feminine vibe. She'd admit in 2026 that she embraced method dressing, even when it didn't feel totally authentic. "... It's kind of to a level where it almost becomes a costume. I'm not into that with fashion," Lopez told InStyle.

Now one of the most famous celebrities in the world, it's no surprise designers were bending over backward to work with Jennifer Lopez by 2003 (the year after she released her own clothing line, JLo by Jennifer Lopez). Her stylist at the time told Glamour they secured her a gown for the Oscars previously worn by Jackie Kennedy Onassis. "I scoured through books and worked very closely with the Valentino team to select an incredible and meaningful dress from the archive," they said. That was a stunning, one-shoulder, light green number with a lace, leaf-inspired hem that cemented Lopez's place in fashion history.

While that ensemble was more conservative, Lopez still gravitated toward plunging numbers. For the "Gigli" premiere, her rom-com with then-fiancé Ben Affleck, she stunned in a Gucci by Tom Ford brown, satin gown with an open chest and central slit. The dress proved Lopez had well and truly arrived on the high fashion scene.

Having divorced Cris Judd, called off her engagement to Ben Affleck, and married musician Marc Anthony, Jennifer Lopez announced in 2007 that she was expecting twins. But pregnancy didn't slow down this fashionista. A source told Female First she'd hired luxury designer Roberto Cavalli to make her a custom maternity wardrobe. "She would never let her stylish image go – not even when giving birth," they claimed.

On the Movies Rock red carpet, Lopez proved that in a Grecian-inspired, one-shoulder white gown that skimmed her growing baby bump for style and comfort. It's not known if that look was from Cavalli, though she added extra glam via her embellished gold clutch and sparkly cuff. The pregnant star also put her best fashion foot forward on stage. While performing with Anthony, she stunned in another flowy fit, this time a turquoise satin gown covered in rhinestones with a tie around her waist to show her shape. She wore the ensemble, a Cavalli creation, to confirm her pregnancy.

2011 was a big year for Jennifer Lopez. She announced her split from Marc Anthony, reinvigorated her music career (via one of her biggest hits, the dance track "On The Floor"), and was appearing on screens weekly as an "American Idol" judge. At the Grammys, her lean away from R&B pop and into dance pop was represented by her mirror Emilio Pucci mini-dress and matching clutch. She added sky-high, silver, open-toe stilettos with studs. Studded pumps were a huge trend, proving Lopez still had her finger on the pulse in her 40s.

Her fashion shortly before confirming her split gave confident breakover (a breakup makeover) vibes. At Capital Radio's Summertime Ball, the month before confirming her split, J-Lo embraced edgy, sassy pieces. She wore a short, snakeskin dress with matching thigh-high boots for a bold, fearless aesthetic that gave us strong, independent woman energy. Snakeskin was trending and proved Lopez could nail trends while staying true to her sexy style. Her "American Idol" gig also renewed interest in her fashion, and media outlets kept a close eye on her style.

Jennifer Lopez had found love again by 2017. She started dating sports star Alex Rodriguez, and the early days of their intense romance may have at least partially inspired Lopez's daring fashion risks. She'd also undertaken a Las Vegas residency, so keeping fit was a high priority to help her perform the high octane show each night. That may explain why she showed so much of her fit figure.

At the Billboard Latin Music Awards, she posed on the red carpet in a barely-there Julien MacDonald black dress with cutouts that showed almost every inch of her figure. "The sexy cut, plunging neckline and open back is something that's become a signature for Jennifer; sexy, feminine, fearless," J-Lo's stylists Rob and Mariel told Billboard, explaining they opted for a dark color so it wasn't too predictable. Backstage, Lopez wore a similar style MacDonald dress in shimmery champagne with large cutouts over the chest and waist and a high, center slit over her legs.

The year Jennifer Lopez won the CFDA Awards Fashion Icon Award, she celebrated two decades since her iconic Versace Grammys moment. J-Lo walked the runway in a redesigned version of the gown during a 2019 Milan Fashion Week show. "The second time I wore it and walked out there, it was such an empowering thing. Twenty years had gone by, and I think for women, knowing you can put on a dress 20 years later—it resonated. It was like, 'Yes, you know, life is not over at 20!'" she told Vanity Fair.

Lopez also took a risk at that year's Met Gala. She fully embraced the theme Camp: Notes on Fashion in her plunging, iridescent beaded Versace dress with a thigh-high slit. She added a statement necklace, bangles on both wrists, large rings, and a beaded headpiece. During a fitting filmed for YouTube, Lopez asked for the slit to be taken higher and for the waist to be taken in further, proving she'd learned a lot over the years and knew how to dress her body.

The world saw another side to Jennifer Lopez's style at Joe Biden's 2021 presidential inauguration. She wore a monochrome white ensemble from Chanel that was appropriate for the grandeur of the occasion. That includes a ruffled blouse, sequins, wide-leg pants, and a long coat. "We went for a very kind of classic, beautiful look. I was very happy to be Latina and representing Latinos in that moment," she told Vogue. The "Maid in Manhattan" star's mix of textures proved that monochromatic looks may be perfect for lazy days, but they don't have to be boring.

Lopez certainly hadn't permanently ditched risqué looks, though. At the MTV Video Music Awards, she wore a David Koma crop-top with a corset fastening across her chest, marking one of Lopez's leggiest looks of all time. She paired it with a daring black and silver miniskirt with corset fastenings on both thighs from the same designer, proving fashion has no age limit (she was 52).

Jennifer Lopez had reunited with and married Ben Affleck by 2024, which had a major influence on her aesthetic. She released the album "This Is Me... Now" and the movie of the same name. "'This Is Me... Now' was a moment in time that was captured that was inspired by falling in love at that time," she told Vogue.

Her 2024 Golden Globes look represented her in-love state of mind. The romantic, strapless, light pink, custom Nicole + Felicia Couture gown featured a wedding dress-esque train and over-the-top rose sleeves. She added drop, pink stone earrings, and wore her hair in romantic waves. The star's loved-up, softer side was also evident in her boho-inspired white, tiered, plunging Chloé dress that showed plenty of leg at a Mexican "Atlas" movie event. She paired it with an undone, soft up-do that was just as romantic without distracting from the dress.

Jennifer Lopez and Ben Affleck's rekindled romance ended in August 2024 — and Lopez dressed for revenge after the split. Her looks in the latter half of the year marked a drastic departure from her earlier 'fits, as they were noticeably edgier and more provocative. At the "Unstoppable" movie premiere, one of her first red carpet appearances since filing for divorce, she went undergarmentless in a long, mirrorball-esque dress with nothing but large, black bows holding it together. Lopez told People she was advised not to wear the Tamara Ralph gown. Her response? "I was like, f**k it."

She also wowed in a sheer-illusion gown at the Governors Awards. The beaded, Zuhair Murad number had a long, black train (a far cry from the pink one she wore a few months earlier). Though the sheer-illusion material tapped into J-Lo's glitzy, sexy aesthetic, the dark, gothic vibe may have represented her personal struggles. She spoke to Interview about the internal work she did following her fourth divorce, admitting, "It feels lonely, unfamiliar, scary. It feels sad. It feels desperate."

Jennifer Lopez had a drastic style transformation after divorcing Ben Affleck. She told "CBS Sunday Morning" she learned a lot about herself post-split, which was demonstrated in her wardrobe. At a pre-Grammys gala, her confidence was back to maximum. She wowed in a plunging metallic gold and dark pink LaPointe dress with a jewel-inspired clutch, dark nails, and statement earrings. She wasn't hiding behind her hair either, as she styled it into a smooth updo. J-Lo told InStyle that year of her evolving style, "I want to always feel more original."

The "Save Me Tonight" singer wasn't looking to blend into the background at the Formula 1 Grand Prix in Saudi Arabia either. She arrived in a pink, latex jumpsuit by an unknown designer with see-through heels and pink sunglasses, ensuring all eyes were on her in her single era. A few months later, she clapped back at her fashion haters. Admitting she'd seen comments suggesting she should dress her age (she was in her 50s), she retorted during a 2025 concert (via TikTok), "I said, 'If you had this booty, you'd be naked too.'"

After decades of ups and downs, Jennifer Lopez had finally found herself by 2026. She'd remained publicly single and was spotted in less glitzy, more refined outfits that represented her transformation. On Instagram, she wore a classic white shirt with undone buttons and a long, high-waisted muted green skirt and waist belt, both from unspecified designers. She carried what appeared to be her Hermès Crocodile Birkin bag — which screamed old money — with timeless gold hoop earrings.

That same month, she appeared at An Unforgettable Evening in all black. That included a plunging slip dress over a longline blazer from an unconfirmed designer. The deep V confirmed Lopez still had a penchant for sexy looks (and why shouldn't she?), but the structured blazer with bold shoulder pads signified a sophisticated new style era. 

"I think it's all about learning about yourself. It's all about knowing yourself," she told El País of her new life chapter. "And, when you do that, you're able to be more self-aware. And that self-awareness is a very empowering thing," she added, sharing she was genuinely happy. That suggests plenty more meaningful looks are on the way from this ever-evolving, "Unstoppable" fashion superstar.