The Worst-Dressed Celebrities In VMAs History

Beyond high-profile events like the Met Gala and the Academy Awards, one of the most iconic venues for eye-popping celebrity fashion is the annual MTV Video Music Awards (VMAs). Even though there have been a bevy of unforgettable ensembles on the stage since before the turn of the millennium (not to mention some of the biggest scandals to ever hit MTV), there have also been a ton of terrible (and even controversial) ones. From over-the-top frocks and baffling bedazzled jumpsuits to barely there dresses seemingly made of bits of string, there's been no shortage of scandalous outfit choices at the decades-old awards show. "You get bored," actor Uma Thurman once told The Hollywood Reporter of red carpet fashion (via Evoke). "That's when you have to say, 'I will be worst-dressed.'"

That's not to say that every celebrity is willing to go full throttle at the legendary ceremony. Some are happy to keep things cozy throughout the hours-long event. "I think the key to the VMAs is ... being comfortable," Ciara once said of her fashion choices for the annual show (via ET).

No MTV VMAs fashion list — good or bad — is complete without Rose McGowan's unforgettable sheer black "dress" (er, string of strings). Accompanied by then-boyfriend Marilyn Manson, McGowan says the daring look was her way of making a public statement after being sexually assaulted. "Most of the women that are dressed like that on the red carpet, it's a calculated, sexy move to turn people on," she told Yahoo! Entertainment. "Mine was like, 'I'm gonna f*** with your brain. I'm going to blow your brain up.' And nobody had done it."

Side by side with her then-beau Tommy Lee, "Baywatch" babe Pamela Anderson showed up to the 1999 VMAs feathered and frocked in a puffy pink hat, skintight white corset, and sequined patterned pants. The bizarre ensemble immediately became iconic in both positive and negative ways and even turned into a Halloween costume the likes of Kim Kardashian became known to wear. As for its legacy in fashion history? "I didn't really know what to expect," designer Ivy Supersonic recalled to The Hollywood Reporter about the outfit. "[S]o I gave the [pink] hat [to Tommy], and he was like, 'Oh dude, it's sick. Pam's gonna love it.'"

We all know about Lil Kim's unforgettable pasty-featuring jumpsuit she donned at the 1999 VMAs. But the most unforgettable part of the look came from what happened while she was wearing the purple ensemble. While presenting an award on air, Kim's co-presenter, legendary artist Diana Ross, playfully tapped the underside of Kim's exposed breast. Many were up in arms over the moment, but Kim herself was mostly unbothered. "Honestly, I think she was just giving me a little motherly tap," she said in an interview with Carson Daly. "Like, 'Girl, do you know you have a boob hanging out?'"

Even at the beginning of her decades-long career, Pink was pressed to try all sorts of different avenues to express herself. Fashion was one of them, and at the 2000 VMAs, she took a chance by combining a mash-up of materials. From the extreme low-rise jeans to the floor-length fur coat, a gold cropped halter top, platform heels, and pink-spiked hair, she was a walking billboard for the turn-of-the-century style — and not in a good way.

Many have wondered what happened to 2000s-era one-hit wonders like Macy Gray, but what they haven't forgotten is Gray's self-promotional gown at the 2001 VMAs. Sporting an oversized flowery newsboy cap, the singer's funky style seemed relatively normal — until you realized the rest of her outfit was a garish pink and blue gown bearing the words "My new album drops Sept. 18 2001." Even better, the back of the gown said "Buy It." Gray donned the daring look onstage alongside Mary J. Blige and Nelly later that night, but it's hard to think that it didn't steal the entire focus of the audience both in the room and at home.

For someone whose fashion pretty much defined the turn of the millennium, Britney Spears' 2002 VMAs look was an unforgivable miss. Part leather bodycon, part lace-frilled lingerie, in theory, it could've worked. But mixing in an asymmetrical cut near the thigh, sky-high wrap-up heels, a tiny ruffle train, fingerless mesh gloves, and a matching leather newsboy cap, the overall look felt more Village People than video vixen.

Rock star Lenny Kravitz has been known to show a lot of skin over the years, but at the 2004 VMAs, even that chiseled chest couldn't save the confusing ensemble he donned over it. Kravitz showed up in a classic pair of jeans and boots, but what he wore on top could only be described as a fringe of frayed denim strips draped across him like shoulder pads. Later on when he performed onstage, he added a mini pair of angel wings to the back of the confusing accessory, or top, or whatever it was. It was confusing, to say the least, but at least it matched the bottoms, right?

As she kick-started her solo career, Fergie's first foray post-Black Eyed Peas at the 2006 VMAs was, for many, a confusing time. The shorts? Teeny tiny. The top? Schoolgirl, long sleeved, and cropped beyond cropped. Add in the super small necktie, the puddle jumper-esque boots, and a jauntily placed bowler hat, and the whole look screamed excessive. The "London Bridge" singer may have followed a (somewhat) British, plaid-wearing schoolgirl theme, but the overall execution was confusing at best.

There's something to be said about a commitment to a bit, so no one can fault Lil Mama for doing just that at the 2007 VMAs. What one can say is that the outcome of the young rapper's ensemble was questionably effective. Donning a silky satin babydoll dress with a hood and sporting a diamond-encrusted pacifier in her mouth, the "Lip Gloss" artist certainly ran with her namesake's take on fashion. She even took it one step further and related it to her overall genre. "This is the birth of hip-pop, and I'm basically the baby of that," she boasted to Just Jared at the time. "Keeping it fresh with my styz-ile."

Anyone remember the beginning of Nicki Minaj's career, when she dubbed herself the "Harajuku Barbie" and sported tons of colorful, accessory-driven outfits to support that title? One of the most infamous of those was at the 2011 VMAs, where the rapper appeared in an ensemble that can only be described as part metallic bodysuit and part stuffed animal menagerie. Her pink and yellow sky-high wig, an ice cream cone necklace, and a patterned face mask (long before the pandemic days) were just a few of the larger-than-life pieces that created the memorable ensemble. Even though she was trying to pay homage in her own way, the sheer volume of collected pieces turned said homage into something that leaned more outlandish than lovingly inspired.

2013 was a big year for Miley Cyrus, and in the opinion of many, for all the wrong reasons. During her "Bangerz" era, Cyrus' wild style took center stage at the VMAs, particularly during her performance of her hit "We Can't Stop." She wore nothing but her flesh-colored bra and panty set covered by a furry onesie with an animated bear face on the front. Though she admits the ensemble carried controversy, she shared that the inspiration for the outfit came from a more personal place. "This was inspired by a Todd James sculpture that I had fallen in love with," she explained to Vogue. "The bear reminded me of myself for some reason. I thought it was beautiful."

From one pop star to another, Katy Perry paid tribute to Britney Spears with her 2014 VMAs look. Alongside rapper Riff Raff's denim-forward Canadian tuxedo, Perry strutted her stuff in a strapless denim gown, hearkening back to Spears and Justin Timberlake's similar ensemble at the 2001 American Music Awards. In Perry's view, it was nothing but respect for her pop princess. "That moment Britney gave us was the moment, and I wanted to pay my respects," she told Mo Heart on the Amazon Music digital series "The Walk In" (via Variety).

Miley Cyrus made her way back to the VMAs in 2015, but this time, as a host — and even more scantily clad. Among her multiple outfit changes, the singer kicked off the night with a barely there red carpet look that consisted of a crystal-embellished, see-through skirt and two strips of silver fabric that covered a small portion of her chest. Her hair was whipped into a sky-high ponytail, and she accented it all with a pair of thigh-high silver boots. It was a moment, for sure, but many questioned if it was a moment worth remembering.

The VMAs have historically been held at the end of the summer, but Farrah Abraham decided to pull out her Halloween costume a bit early for the 2016 show. Donning a Wonder Woman costume straight from Party City, she and her teased brown and blue hair took to the red carpet with a few embellishments of her own. With a pair of sparkling silver stiletto boots and a pop-art-themed arm tattoo, she claimed that the look mimicked her journey as a "Teen Mom" star. "I honestly get bored of the fashionable business look, so I dressed it up, and I love it," she shared with Us. "Business takes over my life, so I wanted to have some fun!"

Despite being the daughter of a music legend, Paris Jackson isn't immune to a few fashion misses. At the 2017 VMAs, the singer went for an ethereal look with a flesh-toned, sheer midi dress, but the series of embellishments atop the material made it fall flat. Large floral patchworks adorned the hem at the bottom, plus the multicolored bodice that cut off at the top confused many viewers. The overall sheer nature of the dress also turned many off because it realistically served as a sort of bathing suit cover-up for the white shorts and bikini-type top she wore underneath. Overall, the vibe just didn't match the execution.

At the 2017 VMAs, Jared Leto took to the red carpet alongside his bandmates from 30 Seconds to Mars in an outfit that seemed made for the Broadway stage. But the colorful bedazzled overcoat he wore ended up giving circus ringmaster rather than "Joseph and the Technicolor Dreamcoat." Paired with a slicked-back hairdo, silver quasi-moon boots, and a ruffled, rose-adorned shirt, the loud patterns just didn't mesh well together. His band may have performed that night, but it's their leader's fashion choice that ended up being the most memorable moment — for all the wrong reasons.

A dominatrix-style ensemble is not something new to the VMAs, but Amber Rose's 2018 edition took it just a little too far on the side of gaudy. The candy apple red outfit included cat ears, garters, a pointed bodice à la Madonna's "Express Yourself," and a short whip. As for the inspiration? Rose had a specific vision for the aura she wanted to give off that night. "I went to my stylist, and I was like, 'I want to kind of look like an intergalactic space s***,'" Rose explained to ET. "And this is what he came up with, and I was really happy."

Maybe part of the reason people were fuming at the 2021 VMAs was due in part to Kim Petras' dominatrix meets baby doll getup. Featuring a black latex mask and matching leggings with an embroidered knit minidress on top, the "Holy" songstress sure made a statement on the red carpet that year. The polarizing look was designed by Richard Quinn, who is known for using vibrant textiles in his work. Though this piece came straight from the runway of his 2021 line, it didn't quite translate to the fashion moment Petras thought it could be.

When she hosted the 2021 VMAs, Doja Cat tested the boundaries of fashion with her six (yes, six) outfit changes throughout the night. The night started off simple enough with runway-fresh looks from Andreas Kronthaler for Vivienne Westwood. But by the time she took the stage to accept the award for Best Collaboration with SZA, she was sporting a neon-hued, worm-like gown with a massive puffed-up headpiece that was heavily reminiscent of Gustav Klimt. Equally baffling was her next Westwood ensemble, which featured a literal chair as her headpiece. Whatever the case, Doja certainly kept all eyes on her that night.

Among the five best and five worst things at the 2022 VMAs, Lizzo's giant, comforter-like gown was certainly among the latter. The voluminous Jean Paul Gaultier look was dark blue in color and massive in scope, accented with a slicked-back hairdo, dark blue lipstick, and hoop earrings. It may have had the potential to be quite the fashion moment for the "Special" singer, but it was just too big to wrap your arms around — literally. At least the artist was in good spirits about it. "My stylist: How much fabric do you wanna wear? Me: Yes," she posted to X after the ceremony.

Sexy siren Tinashe took things to another level at the 2023 VMAs with a barely there outfit that had every eye in the place on her. Clad only in a sparkling mesh fabric with black tape covering her breasts and groin, the "Nasty" singer accented her look with a thin black choker necklace and black platform heels. Mesh ensembles are no stranger to the VMAs, but the lack of fabric underneath was certainly among the first at the annual event.

Despite originally declining to attend the ceremony, Bebe Rexha's appearance at the 2023 VMAs left little to the imagination when it came to her backside. The singer's black gown was tastefully cinched in the front but featured two large holes at the back, exposing her bare behind. Ultimately, she decided to attend the awards show both to support her fellow artists and for the chance to wear said dress. "I do feel like anxiety gets the best of me," she admitted in a since-deleted TikTok prior to the event (via People).

"Diet Pepsi" hitmaker Addison Rae strutted her stuff at the 2024 VMAs in an outfit straight out of the "balletcore" movement. In a white satin elevated bra and panty set with a massive tulle tutu behind her, she looked like she stepped offstage from a wilder interpretation of "Swan Lake." Her ballerina-showgirl aesthetic was quite the combination, and Rae insisted her inspiration came from the pop divas before her like Madonna and Britney Spears. "My favorite VMAs looks of all time are probably every single time Britney came on and performed, but especially when she did 'Satisfaction' [at the 2000 VMAs]," she gushed to People.

At the 2025 VMAs, comedian Megan Stalter took the campy route on the red carpet. Clad in a life-sized coffee cup and accented with a bedazzled Dunkin' Donuts purse, the "Hacks" star brought new meaning to (or perhaps introduced) coffee couture. As for her inspiration? The star was pretty straightforward about her vision. "I wanted to look like a coffee cup. And so I do. Gag it!" she shared in an MTV preshow interview (per BuzzFeed).

Among the worst-dressed stars at the 2025 VMAs, Conan Gray's sailor-meets-Marie Antoinette look was, in theory, a fun idea. It was the execution that arguably marred it. The top half featured billowing sleeves, frilled wrist pieces, a cinched navy corset, and a debonair sailor's hat, but the bottom half is where it went out of control. A frilly tulle underskirt with a navy pinstriped fringe overtop turned the outfit into a mess. To make things even more extreme, designer Erik Charlotte revealed the surprising material that made the ensemble even more outlandish. "Major flowers due to Conan for wearing this full look bc it's made almost entirely of denim and weighs like 30 pounds," he posted in an Instagram Story (via Cosmopolitan).