Gwen Stefani, 1998
It’s unclear when precisely it occurred, but sometime in the late ‘90s, raver fashion transitioned from subcultural scenes to the glamour of the red carpet. This shift is the only explanation we have for Gwen Stefani’s unforgettable ensemble.
While coordinating accessories with one’s outfit is standard practice, it’s not often someone opts to match their hair color directly with their undergarment! That striking choice was just the beginning. Below the belt, Stefani sported a peculiarly futuristic shiny skirt layered over pants, a combination that left many baffled. We’re genuinely relieved this phase in Gwen’s fashion history has concluded
Britney Spears, 2001
In the early 2000s, Britney Spears was avidly shedding her wholesome, bubblegum-pop persona for a more daring fashion statement. Her appearance at the 2001 VMAs in a provocative see-through ensemble left fans bewildered, pondering if she had gone a tad “Crazy” and questioning the whereabouts of the remainder of her attire!
Back then, this lace outfit ignited a flurry of scandal, though it might barely raise eyebrows in today’s more accustomed climate. Unbeknownst to fans, this was just a prelude to Britney’s wardrobe selections, setting the stage for an even more revealing display during her notorious “I’m a Slave 4 U” performance.
Shakira, 2001
Shakira has consistently celebrated her distinct style and musical flair, occasionally involving an extravagant mix of leather and, unexpectedly, feathers. At the 2001 VMAs, the Colombian star made an appearance in lace-up, low-rise leather pants, complemented by a bird feather-adorned halter top.
This ensemble could easily be a fashion misstep for most, but Shakira manages to own it effortlessly! While her current sleek and sophisticated demeanor is admirable, there’s a nostalgic charm to the bold cowgirl-leather phase that accompanied her “Whenever, Wherever” era.
Flavor Flav, 1990
We’re all for dressing comfortably, but rapper and reality star Flavor Flav elevated casual attire to an unprecedented standard at the 1990 VMAs. Flav donned what looked like his coziest pajamas and slippers for the occasion. And in an unusual twist, he added a hot pink Batman mask and his iconic oversized clock necklace to his ensemble.
Maybe he intended to catch some Zs during the ceremony? Regardless, we give him props for his commitment to comfort, even if it verges on the whimsical.
Madonna, 1984
Some red carpet ensembles are so monumental that they define the fashion era in which they appear. Madonna, in 1984, created a global stir with her audacious performance.
Delivering what may stand as one of the most indelible performances ever witnessed in music lore, she provocatively cavorted on stage in a quintessentially ’80s wedding dress, complemented by multiple rosaries adorning her neck. This iconic VMAs appearance continues to influence and be revered by artists even after several decades, attesting to its enduring impact in the entertainment world.
Busta Rhymes, 1997
Busta Rhymes made a bold statement at the 1997 Video Music Awards, stepping out in a full-length kimono-style outfit. Why? Because he could — he’s Busta Rhymes, after all! It’s a lesser-known fact that Rhymes himself was the creative mind behind the attire, a piece from his high-end fashion collection, Bushi Sport. He has consistently been daring, never hesitating to push boundaries, whether in his musical expressions or fashion choices.
His red maxi shirt, pants, and jacket combination from the 1997 VMAs continues to be a topic of discussion. With this ensemble, the rapper introduced the concept of gender-neutral apparel way before it gained its contemporary popularity or social acceptance.
Jessie J, 2011
Singer Jessie J demonstrated remarkable resilience at the 2011 MTV VMAs, refusing to allow a severe ankle injury to deter her from making her appearance. Adorned with crutches encrusted with crystals and a sparkling walking boot, Jessie showed that not even a significant foot injury could hold her back from shining on the red carpet.
Despite her camera-ready smile, the situation was more serious than it appeared. Offstage, the severity of her foot condition was such that she required a bone transplant in her foot—a testament to her dedication despite the painful circumstances.
PJ Harvey, 1995
English singer-songwriter PJ Harvey has always harnessed fashion as an extension of her artistic expression, most notably evidenced by her bold ensemble at the 1995 MTV VMAs. Sporting vivid light blue eyeshadow, exaggerated red lipstick, and flamboyant false eyelashes, PJ’s dramatic appearance ranks high among the event’s most unforgettable moments.
The frequently daring artist defended her choice of striking makeup, claiming she perceived the ostentatious aesthetic as “extremely beautiful.” While her perspective is understood, some might respectfully diverge on that point of view.
Avril Lavigne, 2021
Former MTV staple Avril Lavigne, absent from the music limelight for some time, sparked enthusiasm with news of her attendance at the 2021 VMAs. However, the anticipation swiftly fizzled upon the reveal of her fashion choice — a glaring hot pink plaid ensemble paired with a glittery bra, a stark departure from her early 2000s aesthetic.
Despite the jarring plaid attire causing us some fashion distress, it’s impossible to overlook the unique touch of the jacket unfolding into a heart shape. It’s also commendable that she’s keeping her trademark intense smokey eyeliner alive!
Lenny Kravitz, 2004
While the MTV VMAs may be known for their relaxed approach to attire compared to other awards ceremonies, it certainly doesn’t justify stepping onto the red carpet without a shirt, a fashion rule even Lenny Kravitz’s impressive abs couldn’t bend at the 2004 VMAs.
The ensemble he donned leaves us baffled, particularly the ambiguous accessory draped over his shoulders — could they be an interpretation of wings? Despite Lenny’s heavenly vocal chords, this look plummeted straight into the abyss of fashion faux pas. From the excessive fringed collar to the perplexing wing-like attachments, this outfit struck many discordant notes. It’s a style chapter we’re more than ready to close and never revisit “Again.”
Beyoncé, 2016
Beyoncé has always been a thrilling presence on the red carpet, but the excitement reached new heights when she appeared with her endearing daughter, Blue Ivy, both donning coordinated glittering attire, sending the “BeyHive” into a frenzy!
With her sparkling tulle dress, Blue Ivy emerged as a budding style icon, while Beyoncé exuded celestial beauty in her feather-adorned, wing-like gown, complete with detailed beadwork. On anyone else, this ensemble might seem over-the-top or akin to a costume, but Queen Bey demonstrates time and again her unique ability to master any look, from ethereal, feathered creations to sophisticated gowns, with grace and flair.
Cher, 2010
Cementing her status as a pop culture deity, Cher graced the red carpet in the legendary sheer bodysuit that left an indelible mark in her “If I Could Turn Back Time” music video. Despite the video debuting back in 1989, she dazzled just as radiantly in an updated rendition of the outfit in 2010!
Cher’s audacious bodystocking, a masterpiece designed by Bob Mackie, certainly ruffled feathers, but it was Lady Gaga who eclipsed all when she appeared on stage alongside Cher, donning a dress crafted entirely from real meat. Far from being overshadowed, the seasoned icon harbored no resentment towards the younger star’s spotlight-stealing moment. Instead, she embraced the spectacle with humor, finding the entire affair “hysterical”!
Paula Abdul, 1987
If you’ve ever wondered what a mermaid crossed with a country singer would look like, look no further. Paula Abdul showed up to the 1987 awards show looking like a mermaid that took a job singing at a local honky-tonk.
Wearing a turquoise sequined skirt suit and matching bra, she looked like Princess Ariel’s less-stylish cousin. We know we should cut her some slack, given that it was the late ‘80s, but we just can’t get past it. Between the sequins and the western-style fringe on the jacket, this whole look is “Straight Up” horrible.
Dennis Rodman, 1995
Famed for his distinctive flair, Dennis Rodman was a tabloid constant in the ’90s, thanks to his outlandish antics and equally unconventional fashion choices. In 1995, the ex-NBA sensation assembled a rather intriguing ensemble for that year’s VMAs.
While the upper part of his attire could be considered appealing, it’s the lower half that really draws attention and puzzlement. What was the rationale behind using seersucker fabric for the top part of his jeans? And the choice of a belly chain — what was that about? Nonetheless, it’s heartening to see Dennis embracing his individuality through his fashion explorations.
Megan Fox, 2021
Megan may not be in the music industry, but her ensemble at the 2021 VMAs, or the striking lack of it, became one of the night’s most buzzworthy tales. Accompanied by her fiancé, the rapper-cum-punk sensation Machine Gun Kelly, Megan captivated the shutterbugs, becoming the undeniable focus of their lenses.
Adorned in a sheer gown that left little to the imagination, with her hair styled to a glossy wet look, she combined the audacious outfit with glittering lingerie and elegantly strappy heels. This choice of attire firmly established her as a fashion maverick in Hollywood. Indeed, her presence was so compelling that it nearly eclipsed the attention from her partner’s flamboyant red sparkler of a suit.
Paris Hilton, 2002
While the price tag on Paris Hilton’s ensemble for the 2000 VMAs remains a mystery, it’s tempting to suggest she might have been overcharged given the outfit’s puzzling composition — half a skirt and half a top! However, it’s worth noting that many of us were guilty of owning at least one of these asymmetrical “shark-bite” hem skirts during that era.
Embodying the quintessential early 2000s fashion spirit, Paris Hilton stepped onto the red carpet in coordinating pastel pink attire, with her miniature purse as the ultimate accessory. Donning a skimpy halter top coupled with a skirt featuring an exceedingly low-rise waist (was there any other kind back then?), this get-up, though striking, actually ranks as rather subdued in the context of her typically more provocative fashion choices.
Lady Gaga, 2010
When it comes to coming up with unforgettable VMAs fashion, there is no one like Lady Gaga. In 2010, the artist seemed to be inspired by the meat selection at her local butcher. Wrapped in layers of actual meat, Gaga showed up at the award ceremony in what is considered to be one of the most famous moments in award show history.
While the dress, according to Gaga, was intended to symbolize a protest against the “Don’t Ask, Don’t Tell” policy of the military, it didn’t stop the endless amount of jokes and talk about the gorry getup!
Nicki Minaj, 2011
Choosing the most outlandish VMAs attire from Nicki Minaj’s wardrobe presents a challenge, given her array of daring ensembles. However, this particular get-up makes it seem as though Nicki waged a battle with a toy store’s plush section and emerged both vanquished and adorned by her fluffy foes.
This whimsical, Harajuku-esque number made its debut at the 2011 VMAs, a night that saw Nicki clinch the Best Hip Hop Video award for “Super Bass.” While her legion of Barbz (devoted fans) rejoiced in her victory, they couldn’t help but express concern over the entourage of stuffed companions that appeared to accompany her during her triumphant stage moment.
Kim Basinger, 1990
By the end of the ‘80s, Kim Basinger had cemented her status as one of Hollywood’s most alluring figures, a title earned through her array of steamy roles on the silver screen. Maybe that’s what inspired her to channel her inner Sandy from Grease, post-transformation?
In 1990, for the VMAs, Basinger selected a form-fitting black catsuit, which she paired with a robust leather jacket and a prominent headband, a choice of attire for presenting the “Best Dance Video” award. While her leather jacket is a classic piece many would gladly sport today, her broad, workout-esque headband doesn’t quite harmonize with contemporary fashion tastes—we’d definitely leave that element in the past!
Miley Cyrus, 2015
Donning a bit more than her infamous “Wrecking Ball” music video attire (which was nothing), Miley Cyrus chose an audacious, almost invisible, futuristic ensemble for the 2015 VMAs. Featuring lingerie reminiscent of a chandelier paired with metallic suspenders, Miley tested the boundaries of adhesive solutions as she graced the red carpet in this scanty attire.
Astonishingly, this outfit was just the beginning of a series of equally daring numbers, one of which was a wholly see-through plastic dress adorned with strategically positioned dots. While it’s uncertain how chilly the auditorium might have been, one can only hope there was a kind-hearted soul ready with a sweater to offer her some warmth!
Amber Rose, 2014
Just when it seemed that the era of chains and strings masquerading as “dresses” was behind us, Amber Rose reignited the trend with a vengeance. In 2014, she sauntered down the red carpet, donning a garment that immediately conjured memories of Rose McGowan’s legendary sheer chainmail ensemble from years prior.
In a twist of modesty, despite its revealing nature, Amber’s attire actually concealed more than McGowan’s earlier iteration! Adding to the surprise is the fact that this outfit is merely one in a long line of audacious fashion choices made by the celebrity throughout her career.
Rita Ora, 2018
Embracing the persistent trend of sheer elegance, Rita Ora turned heads as she graced the red carpet in a breathtaking creation by Giuseppe Zanotti. While Rita light-heartedly claimed her choice of the daringly revealing number was due to the weather conditions, it’s undeniable that the dress itself is a masterpiece of fashion artistry.
The gown featured unique, whimsically curving lines meticulously embroidered onto the transparent fabric, serving a critical function beyond aesthetics: they strategically shielded specific regions, saving the singer from any potential wardrobe indiscretions. This ensemble epitomizes the ethos of “if you’ve got it, flaunt it,” blending boldness with high-fashion sophistication.
Christina Aguilera, 2003
While pink feathers might suit flamingos, they’re a challenging statement on the red carpet! In 2003, Christina Aguilera made heads turn at the VMAs, donning a gown engulfed in bright pink plumage. The fuchsia feathers were so overpowering that they drew attention away from her quintessential early-2000s makeup, marked by ultra-thin eyebrows and frosted eyeshadow.
One can only sympathize with those seated next to her during the ceremony, likely contending with stray feathers throughout the evening. This bold fashion gamble certainly left an unforgettable impression, though perhaps not for the intended reasons!