Dressed to impress: 28 iconic celebrity fashion moments

At the 42nd annual Grammy Awards in 2000, it wasn’t the trophies that dominated the conversation — instead, it was Jennifer Lopez’s jaw-dropping green dress. Designed by Donatella Versace, the dress boasted a neckline that plunged down to Lopez’s waist and had a flowy, island-inspired silhouette. The dress was so iconic, in fact, that Lopez modeled an updated version of the gown on the runway for Versace during Milan Fashion Week in 2019. 

At the 2010 MTV Video Music Awards, Lady Gaga caused a real stir by artfully draping her body in actual beef. The dress, made mostly of flank steak, was the brainchild of California designer Franc Fernandez and was later preserved by taxidermists. It’s now on display at the Rock & Roll Hall of Fame in Cleveland. 

In her role as Holly Golightly, Audrey Hepburn inspired a generation of fashionistas as she stood in front of the iconic Tiffany & Co. building on New York City’s 5th Avenue in a form-fitting black gown, chic sunglasses and three strands of thick pearls. The look kicked off the ubiquity of the “little black dress,” an essential element of any fashionable woman’s closet. 

In 1955, filming The Seven Year Itch while wearing a white dress designed by costume designer William Travilla, Marilyn Monroe stood over a subway gate and produced what may be the most memorable movie still of all time. 

Bjork is already widely known for her avant-garde musical and fashion aesthetic, but no red-carpet gown is as memorable as the swan-shaped one the Icelandic artist wore to the 73rd annual Academy Awards in 2001. At the time, many derided the dress as “tacky” and gauche, but the swan dress still endures as one of the early-aughts’s most recognizable looks. 

Christened “Nipplegate,” Janet Jackson and Justin Timberlake’s “wardrobe malfunction” during the Super Bowl XXXVIII halftime show in 2004 earned CBS a $550,000 fine for “indecency.” The fine was ultimately overturned in the courts, but the incident remains the nip slip that will forever live on in infamy. 

Back in 2001, pop stars Britney Spears and Justin Timberlake ruled the airwaves and the gossip magazines. The long-since-separated duo is also responsible for two of the most cringe-worthy looks of the early ‘00s at the American Music Awards. Both dressed head-to-toe in blown-out, patchwork denim ensembles; Spears and Timberlake embody the era’s completely ridiculous style. 

It may be totally out of style now, but in the 1990s millions of American women wanted “The Rachel.” Popularized by Jennifer Aniston’s character on “Friends,” the bouncy layered bob can still be seen in the wild. 

At the tender age of 15, Brooke Shields shocked the world with a sultry, arguably scandalous advertisement for Calvin Klein jeans. “Do you know what comes between be and my Calvins,” Shields purred in the ad. “Nothing.” Criticized for sexualizing a teenager, the campaign was so controversial that the commercial was banned from two television stations in New York City. 

Since described as a symbol for female empowerment, Madonna’s infamous “cone bra” first debuted at a concert in Japan in 1990 following major backlash over her song “Like A Prayer.” In the years following, the Jean Paul Gaultier look has become the single most recognizable garment associated with the singer. 

At the 2019 Met Gala, Kim Kardashian stunned even her critics when she walked out in a form-fitting Thierry Mugler dress that was literally dripping with rhinestones. As to not distract from Kardashian’s “wet” look, her husband Kanye West walked the runway in a simple navy jumpsuit. 

The 2019 Met Gala’s theme was “camp,” and Billy Porter absolutely rose to the occasion. The “Pose” actor was carried into the gala by a series of muscled men, and emerged from his perch to reveal a gorgeous gold gown complete with massive wings. 

Actress Marlene Dietrich made history in many ways, especially in the 1930s, when she was a fashion revolutionary. Dietrich was one of the first women in Hollywood to be photographed wearing pants and was a devoted jeans-wearer in a time when women were still restricted to dresses and bloomers. 

After his days with the Funky Bunch were done, Mark Wahlberg starred in one of Calvin Klein’s most legendary advertising campaigns. Wearing a pair of white Calvins, Wahlberg’s campaign with the brand was so iconic that it has since been replicated by Justin Bieber. 

It’s pretty hard to top the stunning white gown that Princess Diana wore to her wedding to Prince Charles, but it’s the little black number that she wore shortly after their divorce that really turned heads. Now known as the “revenge dress,” Diana wore the gown to a Vanity Fair party in 1994, right around the same time that Charles would admit to an affair with Camilla Parker Bowles, his now-wife. 

Arguably one of the most fashionable men in rock ‘n’ roll, Elton John is also one of its most adventurous. Known for his fur coats, platform shoes, over-the-top sunglasses, wacky headpieces and plenty of rhinestones, the Rocketman’s looks will never be replicated. 

Along with wildly influential shoe collaborations with Adidas, rapper Kanye West has released multiple fashion lines for both men and women. His current line, Yeezy, is known for its minimalist, industrial aesthetic and seriously over-the-top runway shows. 

Since the 2007 debut of “Mad Men,” an AMC show about “ad men” in the 1950s, men all around the world have been trying to emulate the regal, effortless cool of Don Draper, the show’s protagonist, portrayed by Jon Hamm. Dressed in sharp suits, slim ties and classy cufflinks, Draper’s aesthetic is responsible for inspiring countless men to dress just a little better. 

Blending technology and fashion, Bella Hadid appeared at Paris Fashion Week in 2022 in a dress created with a special fiber that was sprayed onto her body right on the runway by designers from French fashion house Coperni. The look took about 10 minutes to complete, and of course, Hadid looked stunning. 

Is there a more influential inspiration in men’s fashion than Bond, James Bond? Probably not. Whether played by Daniel Craig, Sean Connery or Roger Moore, the literary spy’s sleek suits are totally timeless. 

Kicking off the basketball shoe revolution, Michael Jordan’s Air Jordans were created for him but ultimately developed into a global phenomenon. Debuted in 1984, sneakerheads will pay top-dollar for vintage Jordans from that era, and new releases from the brand sell out regularly. 

In the early 1990s, Nirvana kicked off the grunge movement both musically and in fashion. Late frontman Kurt Cobain’s flannel shirts, oversized denim and grungy tees eventually made their way to the runway and continue to influence streetwear styles today. 

Designed by Versace, English actress Elizabeth Hurley turned heads in this vampy, safety-pin-secured black dress at the 1994 premiere of “Four Weddings and a Funeral,” starring her date, Hugh Grant. The dress was so influential, in fact, that it became known simply as “THAT dress.” 

Literally dressed head-to-toe in gold, CeeLo Green debuted “Gnarly Davidson,” his gilded, musical alter ego at the 2017 Grammy Awards. Even though it didn’t exactly inspire many fashion trends, the look did result in countless online memes. 

Wearing the most iconic leisure suit of all time, John Travolta’s character in “Saturday Night Fever” had incredible influence on the over-the-top fashions of the disco era, when lapels were wide, bell-bottoms were huge and feathers ruled the world. 

Throughout her six-decade career, actress Katharine Hepburn remained a fashion icon. Responsible for bringing androgynous dress to the mainstream and normalizing women’s blazers and trousers, Hepburn’s classic aesthetic is still fashionable today. 

The early ‘90s were a particularly colorful time for fashion, and Will Smith was no stranger to bright hues during his run on “The Fresh Prince of Bel-Air.” Known for his zebra-striped (and other printed) Zubaz pants, Nike shoes and oversized denim, Smith’s looks on the show are some of the era’s most iconic. 

In recent years, few artists have pushed the boundaries of fashion like Harry Styles. The One Direction alum is known for his androgynous looks, including a fantastical sequined jumpsuit from his 2022 performance at Coachella alongside Shania Twain, and a floor-length ruffled dress on the cover of “Vogue.”