16 of the Most Iconic Celebrity Outfits of All Time 2023

If there is one thing celebrities love, it’s dressing up. Whether it’s walking the red carpet at an Awards show, making an appearance at a movie premiere, or performing in front of thousands of fans, celebrities want to be the center of attention. The easiest way to do this is by wearing an outfit that catches everyone’s attention.

Iconic celebrity outfits range from Jennifer Lopez’s stunning green dress she wore to the 42nd annual Grammy Awards in 2000 to Lady Gaga’s controversial meat dress, which unsurprisingly, was made up entirely of cuts of meats. These outfits have stood the test of time and are still remembered by entertainment fans and fashion lovers. While not all of them are exactly iconic for the right reasons (Britney Spears and Justin Timberlake’s double denim setup anyone?), these outfits made an impact one way or the other that still reverberates today.

Read on below and marvel at some of the most iconic celebrity outfits and wonder how these celebs got away with it. 

16 of the Most Iconic Celebrity Outfits of All Time

1. Kim Kardashian’s All-Black Ensemble

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Kim Kardashian could fill up an entire list of iconic outfits, but it’s hard to go past her 2021 Met Gala dress. The all-black ensemble from Balenciaga (who are in the news for all the wrong reasons these days) not only covers her body but also her entire face. It comprises a long-sleeve turtleneck bodysuit under an oversized T-shirt dress with a pleated train, jersey boots, and matching gloves. Then there is the face mask that covers her entire face. 

“I fought against it. I was like, I don’t know how I could wear the mask. Why would I want to cover my face?” Kim Kardashian told Vogue. “But Demna [creative director at Balenciaga] and the team were like, ‘This is a costume gala. This is not a Vanity Fair party where everyone looks beautiful. There’s a theme and you have to wear the mask. That is the look.’” Mission accomplished. 

2. Jennifer Lopez’s Green Dress 

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During the early years of her career, Jennifer Lopez was never one to back away from wearing something eye-catching. That’s exactly what she did when she attended the 42nd annual Grammy Awards in 2000 wearing a revealing green dress. Designed by Donatella Versace, the dress features a plunging neckline that goes all the way down to Lopez’s waist. Somehow she managed to go the entire event without exposing her goodies, which is a commendable effort. 

Lopez loved the Versace dress so much that she wore an updated version on the runway for Versace during Milan Fashion Week in 2019. She looks just as good now as she did then. 

3. Audrey Hepburn’s Little Black Dress

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Not every iconic celebrity dress is worn on the red carpet. Audrey Hepburn turned fashion on its head with her portrayal of Holly Golightly in Breakfast at Tiffany’s. One of the movie’s enduring shots is of Hepburn standing in front of the Tiffany & Co. building on New York City’s 5th Avenue. Wearing a tight black dress by Givenchy, Oliver Goldsmith sunglasses, and three strands of pearls around her neck, Hepburn is absolutely radiant. 

Hepburn’s look turned the little black dress into a fashion staple that would go on to define women’s fashion for decades. She also helped make the chignon hairstyle popular along with wide-lensed black sunglasses. Truly iconic. 

4. Cher’s Oscar Winning Outfit

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In the late 80s, Cher was arguably at her peak, resulting in the “Turn Back Time” singer winning the Academy Award for Best Actress for her role in Moonstruck. At the award show, Cher wore an unforgettable black number with mesh and sequins that truly dazzled. The dress was the creation of costume designer Bob Mackie and is still one of the most memorable things about that night, besides Cher’s win. 

5. Timothee Chalamet Sparkly Suit

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One of the new breed of young actors taking Hollywood by storm, Timothee Chalamet is also turning heads on the red carpet. He has an unusual style and is never afraid to wear something unexpected. Take this sequined black suit by Louis Vuitton that he wore to the 2022 Oscars. Not only does the suit sparkle, but Chalamet went shirtless. That’s right, a jacket and pants without a shirt. It’s certainly a vibe. 

You might be unsurprised to learn the outfit was picked from Nicolas Ghesquière’s spring 2022 womenswear collection, proving gender is not an issue when it comes to Chalamet’s sense of style. Although Chalamet did pair the outfit with a pair of black ankle boots and silver jewelry to add a slight touch of masculinity. 

6. Lady Gaga’s Meat Dress

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During the mid-00s Lady Gaga was still going through her experimental stage as an artist. Always willing to try new things and push boundaries, she rocked up to the 2010 MTV Video Music Awards wearing a dress made from meat. Designed by Franc Fernandez and styled by Nicola Formichetti, the dress included shoes, a hat, and even a meat purse. 

But it wasn’t just a publicity stunt, with Gaga explaining the dress was a representation of standing up for one’s rights. Speaking with Ellen Degeneres after the award show, Gaga said,  “If we don’t stand up for what we believe in and if we don’t fight for our rights, pretty soon we’re going to have as much rights as the meat on our bones.” 

Despite the goodwill, animal activists weren’t supportive of the dress, which has been preserved and now resides in the Rock and Roll Hall of Fame in Cleveland, Ohio. 

7. Bjork’s Swan Dress

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Bjork has always walked to a different beat than most, so her outfit for the 73rd Academy Awards in 2001 wasn’t a complete shock. The Icelandic artist rocked up wearing a dress in the shape of a swan. The crystal-encrusted bodysuit even featured the swan’s neck and head draped around Bjork’s shoulders. 

Crafted by Macedonian designer Marjan Pejoski, the dress was heavily criticized at the time, but now over 20 years later it is seen as a bold fashion statement and a truly iconic outfit. Björk herself was confused about the reaction she got wearing the dress. “They wrote about it like I was trying to wear a black Armani and got it wrong, like I was trying to fit in,” she told The New York Times in a 2007 interview. “Of course I wasn’t trying to fit in.”

8. Harry Styles’ Black Blouse

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The 2019 Met Gala was camp-themed, with everybody’s favorite former One Direction member Harry Styles absolutely nailing the brief. The U.K. singer-songwriter rocked up in a sheer black blouse by Gucci’s Alessandro Michele that blew everyone away. With painted nails, shiny black business shoes, and a pearl earring, Styles stole the show from many of his female counterparts as he walked the red carpet outside the event. 

9. Britney Spears and Justin Timberlake’s Double Denim

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Remember when the world was a simpler place and Britney Spears and Justin Timberlake were in love? It’s been over two decades since the lovebirds and popstars showed their love by wearing matching double denim outfits to the American Music Awards in 2001. Both were dressed in complete patchwork denim outfits that will have you reminiscing about the good old days when boy bands ruled the airwaves and Spears was the biggest singer in the world. 

10. Marilyn Monroe’s White Dress

Published by Corpus Christi Caller-Times-photo from Associated Press, Public domain, via Wikimedia Commons

Another incredible dress that’s now considered a cultural touchstone, Marilyn Monroe’s ivory number from The Seven Year Itch is something to behold. Created by costume designer William Travilla, the cocktail dress has a plunging neckline and a ballerina-esque bottom half. 

Monroe famously wore the dress during a scene where she stands over a subway grate and remarks, “Ooh, do you feel the breeze from the subway?” as it blows the dress up, exposing her bare legs. This might not seem overly exciting these days, but at the time of the film’s release in the 50s, seeing a women’s legs was scandalous. Nevertheless, the movie was a smash hit, helped solidify Marilyn Monroe as a movie star, and gave pop culture one of its most iconic moments. 

11. Lil Nas X’s 

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Rapper Lil Nas X’s style has visibly evolved since he burst onto the scene with “Old Town Road” in 2019. While cowboy-themed outfits were the norm, X has gone on to become a trendsetter who always wows on the red carpet. From the gold Versace gown he wore at the Met Gala in 2021 to his off-the-shoulder purple dress seen at the 2021 MTV awards, X isn’t afraid to wear something different. 

Case in point; the hot pink cowboy suit he sported at the Grammy Awards in 2020. The Versace outfit came complete with hot pink boots and a cowboy hat. Speaking about the outfit choice with CR Men in 2020, X said, “I’ve been trying to deviate from the norm that most guys wear – suit, tie … So when I saw the [Grammys] look, even as a sketch, I was like, That’s crazy. That’s a talking point. I want to get more in tune with that flamboyant side as well. It’s an ongoing journey.”

12. Madonna’s Cone Bra

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Madonna was always making statements throughout her career. Willing to push the boundaries and spark the ire of conservatives, Madge debuted a cone-shaped bra and corset designed by Jean Paul Gaultier during her 1990 “Like a Virgin” tour. It caused outrage but certainly helped keep Madonna’s name in the public domain, along with helping ticket sales, with the tour going on to be one of the biggest and most successful in the world at that time. 

13. Diana, Princess of Wales’ Wedding Dress

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There are plenty of women who have worn iconic wedding dresses over the years, but none have caused quite the stir as Princess Diana. And not in a negative way, but more due to the fact that her wedding to Prince Charles was one of the biggest events in royal history. Around 750 million people watched the two get hitched, with Diana wowing in a wedding dress designed by David and Elizabeth Emanuel.

The ivory silk taffeta dress – estimated to be worth around $186,000 at that time – featured lace, sequins, hand embroidery, and 10,000 pearls. It also had the longest train in royal wedding history, spanning an impressive 25 feet. 

14. Elizabeth Hurley’s Black Dress

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It might not seem that exciting these days, but at the time Elizbeth Hurley had everyone forgetting her partner Hugh Grant and focusing on her revealing black dress. Showing a good amount of cleavage and plenty of leg, the Versace dress overshadowed everything else that happened at the Four Weddings and a Funeral 1994 premiere. 

15. Rose McGowan’s See-Through Dress

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While dating rocker Marilyn Manson, actress Rose McGowan showed up at the 1998 MTV Video Music Awards in a barely there at all dress. The completely see-through outfit doesn’t leave much to the imagination, with only her downstairs area covered by a g-string. The outfit caused quite the commotion, but not in a good way, with McGowan getting a lot of backlash from the media. 

But McGowan doesn’t regret wearing the dress, informing Jameela Jamil for her I Weigh interview series, per People, “I [wore] that for a reason. It was my first public appearance after being raped. And I thought, it was kind of like Russell Crowe and Gladiator when it comes out in the ring and he’s like, ‘Are you not entertained?’ And that was why I did that. That was my response to being assaulted.”

16. Lil Kim’s Free the Boob Dress

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Speaking of controversy, rapper Lil Kim had everyone talking at the VMAs in 1999 when she arrived wearing a purple dress that exposed one of her breasts, bar for a small shell-shaped pastie that covered her nipple. It led to the infamous moment when Diana Ross grabbed Kim’s boob on stage while presenting an award. It remains an iconic dress and moment that people still talk about today. 

Categories: Entertainment
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