When Jenny from the Block debuted on the music scene in the mid-1990s, she immediately drew a lot of attention from the media and the audience alike. Back in the day, JLo was known for her big hair, short skirts, and velour sweatpants. Fortunately, Jennifer Lopez’s style has matured to the point that she is now regarded as a fashion icon.
Let’s take a trip down memory lane and remember some of the pop star’s most memorable ensembles.
1994
A girl from the Bronx was first spotted in Los Angeles as a backup dancer. However, as soon as she stepped onto the floor, or red carpet, or one of the stages, music producers saw big business in this fierce Latin girl. Jennifer’s ambition and hard work kickstarted her career beyond everything she ever dreamed of.
1997
“Selena” was Jenny’s big break that embedded her name as the highest-paid Latin actress in Hollywood. At the premiere, Lopez wore a classic metallic embellished gown.
The success of her first movie landed her an invitation for the Oscars that same year. JLo showed up wearing the studded dress by Badgely Mishka.
1998
In May of 1998, Jennifer attended MTV Music Awards in Versace outfit.
The actress went with the same designer for her stroll down the red carpet of the VH1 Fashion Awards in October of the same year.
1999
In December of 1999, Jen shocked everyone with the plunging neckline dress that she chose for VH1/Vogue Fashion Awards.
2000
The most iconic look happened on February 23rd, 2000 at the Grammy Awards when Lopez showed up in the famous Versace gown. No one remembers who won the Grammy’s that year. Jenny was the absolute winner in all categories.
In September 1999, at the MTV Music Awards Jennifer matched P. Diddy’s, her then-boyfriend, outfit with white jeans and a bandana.
2001
For the Oscars, the singer picked Chanel’s glamorous dress looking modest compared to her previous outfits. Or did she? Take a better look, the top is completely see-through!
2002
For the 2002 Academy Awards, Lopez looked stunning in a pale pink Versace gown and a 60s inspired hairdo.
May of 2002 was a busy time for the singer. For the premiere of “Enough” where she was the protagonist playing battered woman, Lopez wore a light, pink, sheer dress.
A couple of weeks later, the star made a nod to her roots wearing velour sweatpants, high-heels, and big hoops.
In December, Jennifer Lopez had another movie premiere – “Maid in Manhattan”. The actress wore a nude-colored Vera Wang classic dress.
2003
At the premiere of “Daredevil” in February of 2003, Bennifer showed up in matching black outfits. Lopez was wearing a strapless black gown while Ben Affleck donned a classic black suit and white tie.
A month later, the singer came solo wearing a stunning Valentino gown.
In August, at the “Gigli” premiere, the couple showed up looking glamorous again. Jennifer was wearing a Gucci jumpsuit, with a belly button-deep neckline.
On Halloween, Jennifer showed up in a strange-looking Dolce&Gabanna gown. Maybe it was a costume? In any case, surely this is the look Jenny would like to forget.
2004
By the Golden Globes in January, the romance with Ben Affleck was over, and Jenny swiftly bounced back and went on with her engagements. She attended the event wearing a bright orange Michael Kors dress and golden hoops.
In April, the actress came to the Costume Institute Gala happening to honor her Latino roots looking like a flamenco dancer in a lacy black Dolce&Gabanna dress.
2005
JLo showed up in March of 2005 to promote her new album “Rebirth” at the Virgin Megastore on Times Square. The poncho and jeans combination might look like a fashion flop these days, but at the time it was considered trendy.
2006
Jenny was back on the red carpet of the Oscars wearing a sage Jean Desses floor-length gown. She looked classy and glamorous her hip-hop beginnings clearly fading away. The singer was turning to more mature looks, with subtle jewelry and classic hairstyles.
In May, Lopez attended Met Gala looking like royalty. A simple, white gown by Versace made the popstar the belle of the ball.
In August, at the MTV Music Awards, Jennifer went for a more funky look. She found her groove in Biba’s short sparkly dress paired with a matching headpiece.
2007
Another Oscar event, another great look by Marchesa.
In July, Jennifer showed up in the land of her ancestors, in San Juan, Puerto Rico for the premiere of “El Cantante”. Again, Lopez looked like a superstar in a classic, ruffle dress paired with chandelier earrings.
In September, Jennifer Lopez became a fashion designer when she launched her first show at the Mercedes-Benz fashion week. She walked the runway at the end like a pro. This marked the beginning of the new Jennifer Lopez. She was not only a dancer, singer, and actress, but she was on her way to becoming a highly successful businesswoman.
2008
Only days before giving birth to twins from her marriage with Marc Anthony, Maximilian David, and Emme Maribel, the singer attended a Unicef benefit event wearing a Gucci gown.
By May, Jenny was back to her old self. She made an entrance at the Met Gala wearing an Alberta Ferretti enchanting gown fit for a queen paired with the matching bracelet and big curls.
2009
Golden Globes weren’t as golden as Jenny was that evening. Her Marchesa dress made her look like the main prize.
In November, the singer attended the American Music Awards wearing a groovy feathered mini dress. Hey, we all have our not-so-great moments.
2010
For the Grammy’s of 2010, the Latin diva went back to one of her favorite fashion names – Versace. This time she wore a half-gown, half-nightclub mini dress ensemble.
At the Academy Awards red carpet, Lopez came wearing Armani haute couture white gown.
Later, for the Oscars Vanity Fair afterparty, the star changed into a black feathered Gucci dress.
For the Met Gala in May, the singer chose a studded, strapless Zuhair Murad gown.
Later that month, Jennifer showed up at the World Music Awards wearing a leopard gown.
2011
The famous couple walked the red carpet of The Golden Globes looking like figurines at the top of the wedding cake. Jennifer wore Zuhair Murad’s white gown with the embellished sheer top, while Marc was in an all-black suit.
At the yearly Met Gala, Jenny looked dazzling in a bright red Gucci dress with floral detail.
In November, the star showed up for American Music Awards in Los Angeles in a black lace long dress.
Later that night, jaws dropped when Lopez stepped on the stage wearing a famous Swarowski embellished bodysuit.
2012
Zuhair Murad was Jennifer’s choice when it came to Oscar’s. This time, the dress was custom-made for the diva with the plunging neckline.
Many have forgotten about this unique ensemble. Lopez came to the event wearing a Lanvin dress with a Swarowski snake around her neck and down the left side of her body with the price tag of $8000. A daring outfit was mostly overlooked by the media, unrightfully so.
At the UNESCO gala event, the singer-actress again chose Lanvin gown. This time it was less dramatic.
2013
For her Golden Globes look, the pop star stayed loyal to Zuhair Murad. A classic nude dress embellished with white lace paired with traditional big curls hairstyle made JLo look like the queen of the red carpet.
At the Grammy’s, Lopez showed some leg! High-cut, black dress was designed by Anthony Vaccarello.
In 2013 Jennifer Lopez got her star at the Hollywood walk of fame. She showed up wearing a Dior gown for the event. That’s how a Diva does it!
For a formal Human Rights Campaign National Dinner in Washington, Jenny went for Zuhair Murad’s gown again. Not what the stuck-up investors and politicians are used to seeing.
2014
At the Billboard Music Awards, Jennifer Lopez came to accept her icon award in a red, sheer, high-slit, plunging Dona Karan dress.
In the summer of 2014, at the MTV Video Music Awards, the mom of two wore a Charbel Zoe silver strapped dress paired with studded stilettos.
2015
Zuhair Murad was Jennifer’s choice one more time for the Golden Globes. Deep neckline and high-slit beige gown looked fantastic paired with dramatically pulled back ‘do.
A couple of months later, in March, for the Oscar’s the choice fell on Ellie Saab’s princess-like gown in pale peach decorated with crystals.
For the Vanity Fair Oscar party, Jenny went to her favorite Zuhair Murad.
While in LA, Lopez went to Nickelodeon’s Kids’ Choice Awards wearing Roberto Cavalli mini dress and Jimmy Choo stilettos.
At the Metropolitan Costume Institute Gala event, the singer wore a daring Versace, dragon-inspired gown.
Billboard Music Awards in Las Vegas will be remembered for Jenny’s stunning look. She flaunted her perfect abs in this Charbel Zoe naked gown.
For Tony Awards, the actress wore an elegant navy Valentino gown embellished with golden details.
2016
Yellow was the color for this year’s Golden Globes! Jennifer Lopez looked like a Hollywood diva that she is in a Giambattista Valli gown.
At the Latin Grammy Awards, the Latin superstar looked amazing in the striking golden mini-ensemble.
Who can forget Jennifer in a studded leotard at Planet Hollywood Resort & Casino?
2017
Ralph & Russo was the choice for the 2017 Grammy’s. The design was simple and elegant in lilac, with a thigh-high slit and a simple flat hairdo.
For the Met Gala, Jennifer Lopez looked like Disney’s princess in Valentino sky-blue sheer, layered gown.
At the Billboard Latin Music Awards, Jenny channeled her stage personality in a metallic Julien MacDonald gown.
2018
The unforgettable dress by Olivier Rousteing worn by Lopez at the Met Gala event is a true masterpiece. Embellished with golden, red, and blue studs in the shape of a cross at the chest nailed the “Fashion and the Catholic Imagination” theme.
For the Time 100 Gala event, Jennifer went back to her favorite again – Zuhair Murad.
Lopez showed up in a metallic Versace dress for the MTV Music Video Awards.
In December, Jennifer Lopez came to the premiere of the “Second Act” leaving everyone speechless in a huge pink Giambattista Valli gown. Layers upon layers of material were stretching in a long train making the diva the talk of the night.
2019
Once Jennifer Lopez stepped on the red carpet of the Academy Awards event, all eyes were on her. Wearing mirror-like, metallic Tom Ford head-to-toe gown got the town talking about her latest stunning edition.
For the Oscars afterparty, Jenny went for a less dramatic look in Zuhair Murad’s ball gown.
“Notes on Fashion” Met Gala ball was a chance for Lopez to show off her creativity in Versace low-neckline, high-slit gown. A studded headpiece revived the 1920s fashion. Nailed it!
JLo never misses events in her native New York. This time she showed up at the CFDA Fashion Awards at the Brooklyn Museum wearing an appropriate orange one piece with the long, oversized pants that cascaded into a long train.
A glimpse of the 1990s Jenny from the Block vibes was felt when Lopez came to the Hustlers premiere in New York. A high ponytail and name tag bracelet say it all, right?
JLo recreated the iconic 2000s look at the Versace Women’s Spring/Summer 2024 runway in Milan.
An elegant gold metallic dress did the trick for Jenny at the 2019 Academy Of Motion Picture Arts And Sciences’ 11th Annual Governors Awards. Simplicity looks fantastic on her!
2020
The bow-tied whole package has arrived. Jennifer Lopez made a bold statement at the 77th Golden Globes in January of 2024. Valentino designed a floor-length gown tied with a golden bow at the top. Perfect as always.
At the Critics’ Choice Awards, Lopez stunned everyone in a Georges Hobeika’s elegant dress. The gown followed her body line accentuating her waist and neck with crystals. Like a true Hollywood goddess.
Once again, Georges Seboika was behind Jennifer Lopez’s glamorous look at the SAG Awards.
Kim Marks 
Nina Smith