Britney Spears is a cultural icon. An inspiration to millions whose career has influenced everyone from Katy Perry and Taylor Swift to Olivia Rodrigo and Lady Gaga, Spears is an incredible performer who will go down as one of the greats.
Rising to fame in the late 90s with her mega-hit single “…Baby One More Time,” Spears changed the face of pop music. Throughout the early 00s, she dominated the charts and was on the cover of every major magazine. Spears has sold over 100 million records and is widely regarded as one of the most successful artists of all time. Not only is Spears a music megastar, but the Grammy Award winner is also a style icon.
Throughout her career, Spears has never been afraid to cross barriers when it comes to fashion. There is no outfit she isn’t willing to wear and fans have watched her style change over the years with her music. From a shy virginal teen to a sexy vamp and everything in between, Spears has rocked many different types of outfits from the best designers in the world.
2023 marks the 20-year anniversary of Spears’ number one chart-topping fourth album In the Zone, and to celebrate this remarkable achievement, we are looking back on some of Spears’ most iconic outfits that still resonate with fans today. Ranging from red carpet looks to outfits she wore in her most famous music videos, these ensembles still look as good today as they did when Spears first donned them.
Britney Spears Iconic Outfits: 14 of the Very Best
1. “…Baby One More Time” Schoolgirl Uniform
Britney Spears/YouTube
The video clip for Britney Spears’ first single, “…Baby One More Time,” was one of the main reasons why she went from nobody to somebody in 1998. Directed by Nigel Dick, the film clip plays on schoolgirl fantasies, with Spears wearing a schoolgirl outfit that exposes her mid-drift. Incredibly the idea for the costume came from Spears, who was already well aware of how she could use her image to sell records. With her hair in pigtails, Spears straddles the line of sexuality and quickly became a favorite of young boys the world over.
2. “Oops… I Did It Again” Red Catsuit
Britney Spears/YouTube
The lead single from her sophomore album features a music video clip once again from Nigel Dick and another costume idea thought up by Britney Spears. This time she opted for a red latex catsuit that’s both sexual and sensual. Crafted by costume designer Michael Bush, the outfit didn’t come together until the day of shooting but had the desired effect.
The single sold an astonishing 1.3 million copies in its first week, smashing the record for the fastest-selling album by a female artist. It’s a record Spears held onto for 15 years until Adele dropped 25 in 2015, selling a whopping 3.38 million copies in the first week.
3. Matching Tube Top/Knee Pad Combo
Britney Online/YouTube
Performing at Universal Amphitheater during her “Baby One More Time” tour in 1999, Britney Spears had everyone doing a double take with the creative outfit she took to the stage in. Consisting of a pink crop top and white pants, it’s the pink knee pads that make this outfit so iconic. It’s not often you see someone wearing pants with kneepads who isn’t a tradesperson.
4. Old Hollywood Glam
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Rocking up to the 2000 Grammy Awards, Britney Spears showed her wardrobe wasn’t just full of crop tops and schoolgirl uniforms. Spears looked glamorous in a Randolph Duke gown paired with a white fur stole from Oscar de la Renta and a dazzling diamond necklace. This outfit showed another side to Spears and demonstrated she was more than a teen sex fantasy.
5. The MTV VMAs “I’m a Slave 4 U” Look
León Sánchez/YouTube
Britney Spears could always be relied on to deliver something special when performing at award shows. This is when she liked to push the boundaries and surprise her audiences, something she achieved in 2001 at the MTV VMAs. Giving a sexy rendition of her most recent hit, “I’m a Slave 4 U,” Spears appeared on stage wearing a skimpy outfit (green bra and tiny blue shorts) with an albino Burmese python draped around her neck.
Although still young at 19, this was Spears embracing her sexuality and ditching her teen outfits of her …Baby One More Time and Oops!… I Did It Again phases and becoming a woman. It still ranks as one of the most unforgettable moments in VMAs history.
6. Double Denmin Cowgirl
Us Weekly/YouTube
The media had a field day when Britney Spears and Justin Timberlake got together in the early 00s. At that time both were ruling the charts, Spears as a solo singer and Timberlake as a member of NSYNC. Anytime they were seen together was an event, especially when they made their presence felt at the 2001 American Music Awards.
The duo showed up wearing matching double denim outfits that most people could never get away with wearing. But this was Spears and Timberlake, and somehow they made it work. Kurt and Bart designed Spears’ patchwork outfit while Steven Gerstein was responsible for Timberlake’s denim tuxedo.
The outfit was so iconic that Katy Perry and rapper Riff Raff recreated the double denim look at the 2012 MTV VMAs, much to the public’s enjoyment.
7. “Toxic” Sheer Rhinestone-Embellished Bodysuit
Britney Spears/YouTube
The music video for “Toxic” cost around $1 million and is meant to be a mini-movie where Spears plays a secret agent disguised as an air stewardess who kills her ex-boyfriend (Aussie heartthrob Martin Henderson). Model Tyson Beckford pops up while the video also references the sci-fi flick Blade Runner, the TV series Alias, and Marilyn Monroe’s famous upskirt scene from The Seven Year Itch.
There’s a lot going on in the film clip but none of that compares to Spear’s rhinestone-embellished bodysuit. Spears appears to look nude (and there are rumors she might have been) as she rolls around the floor seductively. It’s certainly an outfit you don’t forget.
8. Leather Baker Boy Hat
Victor Costa Productions/YouTube
This outfit is iconic for all the wrong reasons. Deciding to go with a leather dress and accompanying baker boy hat, Britney Spears looked like a biker who lost her way. She debuted the outfit at the 2002 MTV VMAs to a mixed response, and it’s not hard to see why. While you have to commend Spears for always pushing the boundaries of fashion, this was one example that’s iconic for all the wrong reasons.
9. Circus Performer
digitalbritneyspears/YouTube
Kicking off her “Circus” tour in New Orleans in 2009, Britney Spears descendant from the rafters in full circus ringleader gear. Taking the theme from her sixth album, Circus, the outfit also asserted Spears as the one in control of her narrative after several years of controversy in the spotlight.
It might not seem that impressive compared to some of the getups she has worn over the years, but considering where Spears was in her life at this point in time, the outfit has a lot of meaning.
10. Black Bra and Panties
BRENO ALY/YouTube
The less said about pop star Britney Spears’ 2007 MTV VMAs performance the better. But the one thing that did stand out was her outfit or lack thereof. Spears took to the stage wearing a matching black bra and panties ensemble and nothing else. Fans were quick to forgive her horrid showing though as they were memorized by her non-outfit.
11. Hardly There Chartreuse Number
Clevver News/YouTube
After several years away from the spotlight, Britney Spears made her triumphant return to the MTV VMAs in 2016. Nine years since her last performance, Spears took the stage in a revealing chartreuse outfit that set tongues wagging. She had the enviable task of following Beyonce, who at that time was all the rage with her album Lemonade.
It might not have been Spears’ best performance, but her outfit was certainly memorable and solidified her as one of pop’s greatest.
12. Kiss the Bride
Santa Spears/YouTube
Along with fellow pop superstar Christina Aguilera, Britney Spears was part of the raunchy 2003 MTV VMAs show that saw the hit makers wearing sexy wedding dresses. The two were celebrating Madonna’s iconic hit “Like a Virgin,” performing their own rendition when Madge showed up in a black tuxedo. Things got really weird when Madonna snogged both Spears and Aguilera near the end of the song. You can always rely on Madonna to steal the moment.
13. The Naked Outfit
Victor Costa Productions/YouTube
At first, wearing a sequenced black suit, Britney Spears stunned viewers when she ripped the suit off to reveal her naked form, well kinda naked. Spears was actually wearing a nude-colored bra and pants combo adorned with sparkles. This outfit makes the list for not only tricking punters into thinking Spears was naked but for ushering in this new fashion trend that inspired the likes of Jennifer Lopez and Kim Kardashian.
14. Pink Cowboy Hat
britneyspears/Instagram
Britney was on one when she assembled this outfit during her early years. Rocking mid-length gold boots, a bright floral dress, and a pink cowboy hat, you couldn’t miss her coming down the street. It’s a strange combination that somehow works, or maybe the outfit has just dazzled our brains so much we can’t tell what’s good and what’s bad.
Then, in 2022, Spears appeared in photos on her Instagram account wearing the pink hat again. This time it was for her social media account as she snapped pictures of herself enjoying Maui beach. The images are slightly provocative and created a little drama for Spears, as they show her wearing nothing more than the pink hat. A least she was being sun smart.
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