Inappropriate Outfits Britney Spears Has Been Caught Wearing

Since the second she shimmied into the pop music stratosphere as a young and seemingly provocative teenager, the world has been all too privy to the inappropriate outfits Britney Spears has been caught wearing. From day one, pop music's greatest "not so innocent" showgirl has performed an incredible high wire trick, portraying both wholesome good girl and seductive nymph, and winking as she walks the rope between intentional provocation and accidental sexiness.

Throughout her incredible if often troubled career, it's difficult to argue that Spears' style has often been at its best, most interesting, and powerful when she's wearing something a little inappropriate. This is a star who appears to have had a thorough understanding of the industry within which she works, and it's propensity to objectify or otherwise exploit young women for their bodies and sexuality. Spears has always appeared to be ahead of the game on this, seemingly taking charge of her image and persona before anyone has the chance to do it for her. But how much of that is actually true?

As the singer has evolved as an artist and a star, so too have questions pertaining to how much agency and control Spears had and continues to have over her life, image, and career. Whatever the truth has been and will be, there's no denying the star always looks best when she looks happy and comfortable. Even if that means wearing something well against taste, convention, and expectations. Here are some of the best and worst examples.

If we're going to have a conversation about inappropriate Britney Spears outfits, then we have to start with the OG. The teenybopper's "...Baby One More Time" look caused collective pearl-clutching across the country for depicting a teen girl brazenly brandishing her midriff (gasp!) while wearing a school uniform well beyond dress code regulations. The PTA will be hearing about this one, young lady!

Spears, however, was indifferent to the criticism, telling MTV that her belly exposure was a practical choice, not a provocation, "I'm from the South," she said, "you're stupid if you don't wear a sports bra [when you] go to dance class, you're going to be sweating your butt off." Regardless, cultural critics repeatedly slapped her with some variation of a "little Lolita" epithet, seemingly forgetting that Vladimir Nabokov wrote in support of the young woman of "Lolita," and not the people salivating over her.

By all accounts, Spears downplayed the sexiness of her look and appeared to be coming from a place of genuine innocence with it. She suggested to People that the original outfits looked "dorky" and she simply thought that tying the shirts up would "be cute." But was this the absolute truth? Reporter Vanessa Grigoriadis suggested to Entertainment Weekly that she'd been told by "a lot of people" that Spears "wanted to be sexy" while her team wanted her to tone things down, and commented, "I think that it's impossible to know if it's actually true."

The dust had barely settled on the "...Baby One More Time" controversy before another inappropriate Britney Spears look landed the young singer in more hot water. This time, the teen singer posed on the cover of Rolling Stone magazine in her underwear, clutching a shocked Teletubby to her bosom — the toy likely shared the same facial expression of concerned mothers across the country.

A year later the former Mickey Mouse Club star would tell the same outlet, "I don't want to be part of someone's Lolita thing. It kind of freaks me out." It didn't matter what Spears said, people had their doubts. David LaChapelle, the photographer behind the provocative shoot, suggested that Spears feigned discomfort about the set-up while her manager was in the room. "But as soon as he walked out, Britney said 'Lock the door,' and unbuttoned her shirt wide open," he told Rolling Stone. 

Spears told a different story, suggesting to GQ that she felt "tricked" by LaChapelle as she was only 16 and "didn't know what the hell I was doing." Stating that she was of a "naïve mind" during the shoot, Spears said, "Now I look back and I'm like, 'Oh my gosh, what the hell?" (via Britney Boards). Whatever happened between the two, Spears has worked with LaChapelle since, including collaborating on the music videos for "Everytime" and the original, unreleased cut of "Make Me" from 2016 (via IMDb).

By 2000, Britney Spears had obviously heeded the calls for her to put some clothes on, and so she did. For the "Oops!...I Did It Again" music video she covered up her body...in skintight red latex. The video's stylist Estee Stanley told Bustle that although the teen star was "very collaborative" with "Baby One More Time" director Nigel Dick on the video, the "idea [for the catsuit] ... was something she really wanted to do."

It caused an absolute sensation, with The Ringer retrospectively describing how the entire video's "shock and awe defined that moment." A red latex catsuit was one thing, but the way the camera continuously gravitated around the contours of Spears' figure in the thing, was quite another. The song's hook saw the provocateur singing, "I'm not that innocent," which further complicated all discussions around Spears' Lolita image. There was a sexual aggression to the look, which licked at audiences at home like the wet, scarlet tongue of a Tex Avery wolf.

Salon even described the star as "[hitting] the camera with a mad-as-hell body, kicking and slamming against the screen," and ruminated, "She's Barbie as an action figure." However, she was the player, not the doll. As Stanley told Vogue, the star "definitely knew what she wanted" with the look. "People didn't expect it," she said, "She was still young and innocent, and then all of a sudden she comes out in this vixen-like, sexy, skin-tight outfit ... that's what makes her Britney."

Alas, the general public soon became a little desensitized to Britney Spears' bottomless closet of come-hither costumes. It happens to the best of us! However, the "Piece of Me" singer knew one-sure fire way to ensure her 2001 look for the MTV Video Music Awards remained legendary: She used a live snake as a fashion accessory and performance prop. 

According to Mike Hano, the snake handler responsible for helping to bring the striking visual to life, the reptile was an "amelanistic Burmese python" (via Today). Spears was "extremely scared" of the creature "at first," so much so that she told Hana she "broke out in hives everywhere the snake had touched her," as he recalled to Yahoo! Entertainment. It wasn't just Spears who had an adverse reaction to the snake — PETA was predictably furious about the python ... and the live tiger she had on stage with her, too.

Per The Guardian, however, Spears reportedly told the animal rights organization that she'd gotten rid of those elements in the performance after the group had reached out to her regarding "the plight of captive wild animals caged and forced to tolerate bright lights, crowds and frightening levels of noise." But then, she'd already made her impact. Spears entered that stage looking like Raquel Welch in "One Million Years B.C." at some kind of jungle prom, brandishing the snake like a trophy. Inappropriate or not, Spears made history, and she had undoubtedly been crowned queen. 

At this point, nobody needs reminding that Britney Spears endured an incredibly difficult time in the mid-00's. When "Gimme More" was released, it was to be her comeback song — the first single from her eagerly awaited fifth studio album, "Blackout," which saw the media uncharacteristically rooting for the star. However, while the electro-pop track landed favorably with critics, the music video and her overall look did not.

The Guardian's Anna Pickard struggled to make sense of Spears' "Gimme More" look, suggesting the star resembled "a city worker in a cheap suit who's been put through a very hot wash." Pickard further pondered whether this was a deliberate choice, writing, "Perhaps this is a metaphor for Brit's dissatisfaction with The Business." Meanwhile, Entertainment Weekly suggested the outfit was at odds with the video's concept, which left the star "walking in circles around a pole  ... I've seen sexier pole work during an afternoon of fly-fishing," writer Michael Slezak sneered.

It didn't help that the generally blurry vibe of the video bore all the visual quality of a biker babe's bachelorette party filmed on an iPhone 1. Worse still, this should have been Spears' chance to rise from the ashes of her troubles — a proud reinvention — instead, she looked charred. As Slant wrote in its analysis of Spears' image in the video, "It doesn't point to an artist who refuses to evolve, but rather one who doesn't know how — or isn't being allowed to." 

Unfortunately, inappropriate outfits continued to pile-up during the misfired comeback of Britney Spears' "Blackout" year. The star took to the stage of the 2007 MTV Video Music Awards to perform "Gimme More," dressed in a glittery bra and panties paired with fishnets. The outfit looked cheap, ill-fitting, and completely inappropriate for a performer of such stature attempting to remind the world of her immense talent and power.

The result was a critically castigated performance which exposed Spears' vulnerabilities at a time when she was trying to move well beyond them. According to a report by People, sources claimed that Spears "was supposed to wear a matching corset" — which could have tied the look together — but that "she opted out of wearing at the last minute." Another source said, "She was extremely nervous," and claimed that the star "got out there and froze" due to not having performed live "in front of all her peers" for so long.

As The New York Times stated following the show, the performance didn't seem like it would "stem the tide of mean-spirited jokes" about the star. Indeed, Spears had barely left the stage when comedian Sarah Silverman took to the microphone and unfairly sniped, "She is amazing ... she is 25 years old and she's already accomplished ... everything she's going to accomplish in life" (Silverman called her jokes "unfortunate" on Twitter in 2021). In 2007, maybe the only appropriate outfit Spears could have was a thick suit of armor. 

Not every inappropriate Britney Spears outfit was attached to her sexuality or the persona concocted for her by the media. On the contrary, during The Circus tour of 2009 it was a brief incident of cultural appropriation which gave some fans pause. As shared in a Twitter thread on the topic of cultural appropriation in pop music, one tabloid ran with pictures of the star in what they described as her "Indian costume." Which perhaps highlights the problem that The Washington Posts astutely points out with the headline "A culture, not a costume."

According to a set-list shared by the Britney Spears fan-site, the look was deployed for the closing act of the second section of the show. There, the star performed a Bollywood remix of "Me Against the Music," while flanked by backing dancers similarly wearing traditionally Indian regalia. It's quite the set-piece, and the remix does wonders in renewing the track as a live solo piece, as it was originally a duet performed with Madonna.

However, it's easy to argue that the Indian "costuming" wasn't necessary, and that a hat-tip to Bollywood would have sufficed on a musical level without all the additional sartorial bells and whistles. Indeed, that exact notion worked wonders for the star's song "Toxic," which takes its key riff from a sampling of "Tere Mere Beech Mein" from the Hindi romantic tragedy "Ek Duuje Ke Liye" — and without Spears ever adopting Indian garb in the music video to make the reference oblique (via Insider). 

There are few sartorial heartbreaks bigger in this life than finding a perfect beautiful dress, only to discover that A.) it barely covers your curves and B.) it may have also been made for someone several decades younger than you. This appeared to be the position Britney Spears was in when she wore this leather Christopher Kane dress to an "X-Factor" viewing party in 2012. Worse still, her facial expression appears to confirm that she became all too aware of these facts the second those flash bulbs started popping on her. This is not a comfortable woman.

As Pop Crush wrote of the "too tight, too short, and too age inappropriate" dress, "Brit Brit's twins were bursting out of the top" and the fit and styling meant it may "have been better suited to a teenager." Obviously, people of any age should be free to wear whatever the heck they want, but at a certain age there are sadly some looks that cannot contain the complete bodacious body of a fully-grown woman. For critics, this was apparently one of them.

Fashion bloggers Tom and Lorenzo took further issue with the lace paneling at the sides and back of the dress which they groaned was "a bridge too far," and reasoned that the look had potential to be a "step forward" in the star's precarious style evolution, but fell short. "If the entire dress was leather — and the bust fit her correctly — we'd love this look on her," they wrote. 

As her social media followers have long been aware, Britney Spears' Instagram feed is usually one of pure joy. The singer regularly shares videos of herself doing dance routines, strutting around in her fave threads, or beaming with love for her partner and sons. So when the star shares something which derails from that vibe, it really stands out.

In 2021, amidst the legal battle of Spears' conservatorship dispute, the singer started sharing more pointed posts. One of which showed her posing in a latex maid's outfit, with an accompanying caption which appeared to reference claims she made during a court hearing that the conservatorship placed added restrictions on her life (via The Guardian). It read, "My maids may have been able to get their nails done during COVID after salons opened but ... at least my maid outfit was the hottest!" (via The Sun).

Spears is renowned for being playful with her looks on the 'Gram, but from the odd subtext of the look to the concerning caption, the maid's outfit was the first time an outfit felt off on some level. Adding to the concern was the fact that the original post was deleted. The image was later re-shared on Instagram with a new banal caption of some red high heel emojis. Unsurprisingly, fans had grown concerned around this time that the star was no longer in full control of her Instagram feed, as The Mirror reported. Was the maid outfit post somehow connected?

There's one version of Britney Spears' style that every fan favors, and that's the one where she's free to dress as authentically and inappropriately as she likes. Point and case? The original David LaChapelle album cover art for "Glory," which depicted the star chained up in a barely-there gold one-piece — a look which takes on new levels of symbolism given the details which emerged surrounding her longtime conservatorship (via NBC News). Was it inappropriate? Perhaps. But it was also fabulous.

In 2016, however, the album cover art featured a soft-focus close-up of Spears' face instead. An extremely safe music video for "Make Me" was also released from the album in favor of the hyper sexy original also directed by LaChapelle, which was "partially leaked online," per the Los Angeles Times. The same outlet noted these decisions sparked a conspiracy among fans online and the star's team went into crisis mode. "Nobody is hiding anything," Spears' manager Larry Rudolph reassured the paper, "[LaChapelle's] video just didn't work."

Regardless, fans were so outraged they even made a Change.org petition demanding that cover art be changed, because it "is not a suitable representation of the music that Britney is putting out." It took time, but by 2020, Spears announced the new cover on Instagram along with the caption, "You asked for a new 'Glory' cover and since it went to number one we had to make it happen!" — and there she was, in all her glory.