The MTV Video Music Awards (VMAs) stand out as a realm where traditional fashion norms cease to exist. While the event originally aimed to honor musical accomplishments, many of us now eagerly anticipate the fashion spectacle it offers.
From risqué and extravagant ensembles to outlandish red carpet antics, the VMAs consistently deliver one of the most captivating displays in the entertainment industry. Let’s delve into the most attention-grabbing and audacious outfits ever witnessed on the VMAs’ red carpet.
Cindy Crawford, 1992
When supermodel Cindy Crawford took on the role of host for MTV’s House of Style, fans anticipated her bringing her fashion prowess to the 1992 VMAs red carpet. Sporting a leather and lace bustier adorned with numerous straps and buckles, her ensemble exuded daring style.
The provocative gown belonged to Versace’s bold collection dubbed Miss S&M. Cindy relied on her eye-catching dress to make a statement, foregoing the need for additional props like a whip on the red carpet. Notably, singer Dua Lipa also donned a similar look at the 2022 Grammy Awards.
Macy Gray, 2001
Before the advent of social media, artists faced the challenge of finding creative ways to promote their upcoming projects. The VMAs emerged as a prime platform for such endeavors. Macy Gray, the singer, seized this opportunity by transforming her body into a walking billboard. With meticulous precision, she ironed letters onto her dress, boldly announcing, “MY NEW ALBUM DROPS SEPT. 18 2001.”
And just in case anyone missed the message, the back of her dress carried a clear directive: “BUY IT.” Macy’s unconventional DIY PR strategy aimed to generate buzz, but unfortunately, the album failed to make the impact she had hoped for. Despite her efforts, the project didn’t achieve the desired success.
Pamela Anderson, 1999
Let’s face it, subtlety isn’t exactly Pamela Anderson’s strong suit. Just like everything else in the glamorous life of the iconic blonde bombshell, Pamela has a penchant for oversized hats. Embracing the “bigger is better” mantra, Pamela opted for a statement-making headpiece at the 1999 VMAs.
Collaborating with celebrity milliner Ivy Supersonic, she donned a colossal pink hat adorned with feathers. Pairing it with a figure-hugging white corset, sequined pants, and dramatic eye makeup, Pamela exuded the quintessential style of the late ’90s. Accompanied by her then-husband, rocker Tommy Lee, her ensemble left an indelible mark on the red carpet.
Kim Kardashian, 2016
While most celebrities rely on stylists or designers to choose their outfits, Kim Kardashian took a different route by turning to Twitter for advice. Polling her fans on whether she should opt for a “dressy sexy look” or a “casual chill” vibe for the VMAs, Kim ultimately selected a vintage John Galliano dress for the event.
The short, sheer black dress was complemented by a hairstyle reminiscent of just-stepped-out-of-the-pool “wet” hair. Despite the potential awkwardness of walking the red carpet with her estranged ex-husband Kanye West, this dress undoubtedly made a lasting impression.
Rose McGowan, 1998
When your attire steals the spotlight from shock rocker Marilyn Manson clad in a full leopard print suit, you know it’s truly audacious. Rose McGowan left jaws agape when she arrived on the red carpet sporting nothing but leopard print underwear and a sheer beaded “dress.” With her daring ensemble, Rose became a trailblazer for the “less is more” trend in red carpet fashion.
The “Charmed” actress clarified that her choice of attire—a Maja Hanson dress—was intended more as a “political statement” than a mere fashion statement. McGowan’s bold fashion statement undoubtedly sparked conversations and pushed boundaries at the event, leaving a lasting impact on the world of celebrity fashion.
Pink, 2000
Known for her distinctive style and independent spirit, Pink has always forged her own path in both music and fashion. When she made her debut at the VMAs, she seized the opportunity to showcase her unique approach to red carpet attire. Combining elements that defied traditional norms, she donned a sequined halter top that shimmered under the lights, daringly paired with low-rise pants that seemed to defy gravity themselves (the mystery of their staying power remains unsolved).
Adding to the intrigue of her ensemble were her trademark spiky pink hair, defying the laws of gravity, and a statement coat that, one can only hope, was crafted without harm to animals. While Pink’s audacious fashion choices often earn admiration, this particular look may not have been met with unanimous acclaim. Yet, her fearless experimentation serves as a reminder of her willingness to challenge conventions and express herself freely on the red carpet.
Avril Lavigne and Kelly Osbourne, 2003
While the early 2000s were synonymous with hot pink and skin-baring ensembles, they also ushered in a wave of emo and punk-rock fashion. Embracing elements like stripes, skulls, and an abundance of safety pins, this alternative style gained widespread popularity, largely thanks to stores like Hot Topic.
A glance at a picture featuring Avril Lavigne and Kelly Osbourne evokes strong “mom, can you pick us up from the mall?” vibes, encapsulating the quintessential teenage rebellion of the era. The familiarity of their attire likely resonates with many, as it’s reminiscent of the countless individuals who embraced similar looks in high school. In the early 2000s, the emo and punk-rock aesthetic not only dominated the fashion scene but also served as a form of self-expression for a generation eager to break free from conventional norms.
Lil’ Kim, 1999
Few fashion moments rival the unforgettable sight of rapper Lil’ Kim donning a lavender jumpsuit, accessorized with a single seashell-shaped sequined pastie covering one side of her chest. Stepping out to present the “Best Hip-Hop Video” award alongside the legendary Diana Ross, Lil’ Kim certainly left a lasting impression on the audience.
As if her outfit wasn’t enough to turn heads, Ross added to the spectacle by playfully jiggling Lil’ Kim’s exposed side. And for those curious about the pastie’s secure placement, Lil’ Kim’s stylist relied on eyelash glue to ensure it stayed put throughout the event. This iconic moment not only solidified Lil’ Kim’s status as a fashion trailblazer but also served as a testament to her fearless approach to self-expression on the red carpet.
Gwen Stefani, 1998
Sometime during the late ’90s, the once-underground raver fashion seemed to transition from the club scene to the red carpet, and Gwen Stefani’s look serves as a prime example of this phenomenon. While it’s uncertain exactly when this shift occurred, Stefani’s ensemble epitomizes the eccentricity of the era. Matching one’s hair color to their bra is a bold move that few would dare to attempt, yet Stefani effortlessly pulls it off.
Above the belt, her outfit is a masterclass in unconventional accessorizing. With a shiny, futuristic skirt layered over pants, Stefani embraces a daring style that defies convention. While some may find her ensemble perplexing, it undeniably captures the spirit of experimentation and individuality that defined late ’90s fashion. As this chapter in Gwen’s fashion evolution draws to a close, we reflect on the fearless creativity that she brought to the red carpet during this era.
Jared Leto, 2017
While women often receive recognition for their daring and bold red carpet styles, there are certainly fashion-forward men who command attention as well. Case in point: the lead singer of Thirty Seconds to Mars, who made a statement with his unconventional ensemble. Resembling an Amish farmer with a side gig as a children’s party magician, he donned a sequined Gucci cape that demanded attention.
As he graced the VMA stage, all eyes were on him, mesmerized by the shimmering sequins reflecting the stage lights. This actor/singer certainly left a lasting impression with his glorious garment, earning him the nickname “Jared and the amazing technicolor dream coat.” His fearless approach to fashion serves as a reminder that creativity knows no bounds, regardless of gender, and that the red carpet is a canvas for sartorial expression for all.
Lizzo, 2019
Lizzo continues to challenge conventional norms, demonstrating that fabulous fashion knows no size limits. Renowned for her creative and playful approach to red carpet attire, the singer made a bold statement with her ensemble at the 2019 VMAs. Adorned in a custom red sequin Moschino gown emblazoned with the word “SIREN” in shimmering silver sequins, Lizzo exuded confidence and allure.
She accessorized her look with a matching red feather boa and a glamorous bouffant hairstyle, channeling the essence of a sultry siren. By confidently rocking red on the red carpet, Lizzo shattered stereotypes and showcased her individuality, proving that captivating fashion transcends size and embraces diversity. Her fearless embrace of personal style serves as an inspiration for individuals of all shapes and sizes to embrace their uniqueness and express themselves boldly.
Kim Basinger, 1990
By the late 1980s, Kim Basinger had cemented her status as one of Hollywood’s most alluring leading ladies, thanks to her captivating performances in numerous sultry film roles. It’s perhaps this allure that led her to channel the post-makeover Sandy from Grease for a memorable red carpet appearance.
In 1990, while presenting the “Best Dance Video” award at the VMAs, the actress donned a figure-hugging black catsuit paired with a robust leather jacket and a chunky headband. While the leather jacket remains a timeless fashion statement even today, the thick workout-style headband was a choice that didn’t quite resonate with contemporary tastes. Nonetheless, Basinger’s bold fashion choices on the red carpet continue to captivate and inspire, showcasing her penchant for embracing diverse styles and eras.
TLC, 1995
At a certain juncture in fashion’s evolution, we witnessed the rise of the “shipwrecked” trend, wherein individuals willingly paid for clothing that appeared distressed or destroyed. This unconventional fashion movement reached its zenith with the toilet-paper-inspired ensembles donned by R&B girl group TLC at the 1995 VMAs. Departing from their signature oversized and baggy attire, Chilli, the late Lisa “Left Eye,” and T-Boz opted for mummy-like costumes for the prestigious awards ceremony.
While their hit song “Waterfalls” garnered multiple accolades, their avant-garde outfits failed to resonate with fashion critics and fans alike. Despite their experimental foray into unconventional fashion territory, TLC’s sartorial choice at the VMAs serves as a reminder that even the most successful musical acts aren’t immune to occasional fashion missteps.
Katy Perry and Riff Raff, 2014
Witnessing Justin Timberlake and Britney Spears boldly step onto the red carpet clad in matching head-to-toe denim was a moment many believed to be once-in-a-lifetime. However, just over a decade later, Katy Perry and rapper Riff Raff revived the iconic look at the VMAs, putting their own spin on the Canadian tuxedo.
Injecting their rendition with a generous dose of bling, Katy and Riff Raff paid homage to one of the most memorable red carpet ensembles in history. Despite the daring fashion choice, Katy Perry effortlessly pulled off the look, perhaps aided by her vintage-inspired hair and makeup. Their homage to the denim duo certainly made waves at the event, reaffirming the enduring impact of Timberlake and Spears’ original denim explosion on the fashion world.
Christina Aguilera, 2002
The early 2000s marked a peculiar era in fashion, characterized by ultra-short skirts, a penchant for hats, and a tendency for unconventional uses of clothing. Christina Aguilera epitomized this unconventional trend by fashioning what could possibly be the world’s tiniest top out of a scarf. Departing from her usual leather pants and bikinis, the singer opted for this equally revealing ensemble following the success of her hit “Dirrty.”
Despite the daring nature of her outfit, Christina managed to navigate through the entire awards show without experiencing a wardrobe malfunction, a feat that left many in awe. Her bold fashion statement serves as a testament to the daring and boundary-pushing spirit of early 2000s fashion, where creativity and individuality reigned supreme on the red carpet.
Lady Gaga, 2009
When it comes to VMAs fashion, Lady Gaga reigns supreme as the ultimate trendsetter. The singer, known for her avant-garde style, made waves by donning a total of five distinct outfits throughout the show, each more eccentric than the last. For her acceptance of the “Best New Artist” award, Gaga opted for a bold red Alexander McQueen dress paired with a matching face cover and crown, exuding an aura of regal eccentricity.
The unconventional ensemble appeared to bewilder award presenter rapper Eminem, who struggled to conceal his confusion over Gaga’s unconventional attire. Little did Eminem know that Gaga was far from finished with her sartorial surprises, as she later made a grand entrance in her now-iconic “meat dress,” solidifying her status as a fearless fashion trailblazer on the VMAs stage.
Madonna, 1984
Certain red carpet looks become so iconic that they define the fashion of an entire decade. In 1984, Madonna set the world abuzz with her daring performance. In what stands as one of music history’s most memorable moments, the singer captivated audiences as she gyrated on stage in an ’80s-style wedding gown, adorned with a cascade of rosaries around her neck. Madonna’s fearless display of individuality and rebellion against societal norms left an indelible mark on pop culture.
Even decades later, artists continue to draw inspiration from this infamous VMAs appearance, cementing its status as a timeless and influential fashion moment. Madonna’s bold and boundary-pushing style at the VMAs serves as a reminder of the power of self-expression and the enduring impact of fashion on popular culture.
Jennifer Lopez, 2000
Jennifer Lopez is renowned for her ability to make a lasting impression with her fashion choices. While her green dress at the 2000 Grammy Awards remains etched in the collective memory, her coordinated all-white ensemble with then-boyfriend Sean Combs at the MTV VMAs that same year also left an indelible mark. Sporting a bedazzled shirt from her ex-boyfriend’s label, Sean John clothing, and a matching bandana, J.Lo effortlessly infused a touch of femininity into streetwear.
Though her relationship with Sean Combs has long ended, Lopez’s sartorial prowess continues to captivate, with the singer still rocking crop tops decades later. This iconic fashion moment serves as a testament to Lopez’s enduring influence on both the music and fashion industries, solidifying her status as a style icon for generations to come.
Destiny’s Child, 2001
In 2001, R&B girl group Destiny’s Child took a daring fashion turn with their coordinated suede and turquoise ensembles. However, what could have been a statement ended up as a questionable choice, as the trio sported matching suede fringed dresses in an unusual orange hue.
Whether the abundance of orange suede was due to a sale or a stylistic misstep remains uncertain, but the outcome was three outfits that missed the mark. While Beyoncé managed to fare better in the ensemble, Kelly Rowland’s heavy necklace seemed to weigh her down. One can only hope that these Western-themed outfits have since been relegated to the depths of their closets, sparing their necks from further strain and ensuring their fashion choices remain firmly in the past.
Lenny Kravitz, 2004
At the 2004 MTV VMAs, even Lenny Kravitz’s chiseled physique couldn’t salvage his perplexing fashion choice. Opting for a shirtless ensemble, Kravitz left many scratching their heads with his unconventional attire. Across his shoulders hung what appeared to be some sort of wing-like embellishments, adding to the overall confusion of the look.
While Kravitz may possess an angelic voice, this particular outfit seemed more akin to a fashion faux pas. The addition of a long fringed collar and angel wings only added to the bewildering nature of the ensemble. Suffice it to say, this fashion misstep is one we’d prefer not to witness “Again.”
Nicki Minaj, 2011
Nicki Minaj is no stranger to bold fashion statements, and her outfit at the 2011 VMAs certainly turned heads for all the wrong reasons. Resembling a chaotic mishmash of stuffed animals from a toy store, her Harajuku-inspired ensemble left many puzzled. Despite the unconventional attire, Minaj managed to snag the Best Hip Hop Video award for her hit song “Super Bass.”
While her devoted fan base, known as Barbz, celebrated her win, they couldn’t help but express concern over the plethora of stuffed animals seemingly trailing behind her onstage. Minaj’s fearless approach to fashion continues to captivate and divide opinions, with this particular outfit serving as a prime example of her penchant for pushing boundaries and embracing the unexpected on the red carpet.
Megan Fox, 2021
Despite her status as a non-recording artist, Megan Fox made waves at the 2021 VMAs with her headline-grabbing outfit. Accompanied by her fiancé, rapper-turned-punk-rocker Machine Gun Kelly, Fox commanded attention on the red carpet. Sporting a daringly sheer dress and wet-look hair, she paired her bold ensemble with bedazzled underwear and strappy heels, showcasing her fearless sense of style.
The actress’s risqué look solidified her reputation as one of the most trendsetting women in Hollywood, garnering widespread praise and admiration. In fact, her ensemble was so attention-grabbing that it overshadowed her beau’s sparkly red suit, highlighting Fox’s undeniable star power and fashion influence on the VMAs stage.
Beyoncé, 2016
Beyoncé’s appearances on the red carpet always generate excitement, but when she arrived accompanied by her adorable daughter Blue Ivy, dressed in coordinated sparkly ensembles, it sent the “BeyHive” into a frenzy! Blue Ivy stole the spotlight in a shimmering tulle dress, showcasing her budding fashion sense. Meanwhile, Beyoncé exuded angelic charm in a feathered, winged dress adorned with intricate beading.
While such an outfit might appear costume-like on others, Queen Bey effortlessly elevated it to a statement of elegance and sophistication. This mother-daughter fashion moment not only showcased their bond but also demonstrated Beyoncé’s ability to captivate in any ensemble, from feathered wings to exquisite evening gowns.
Miley Cyrus, 2015
Miley Cyrus made a bold fashion statement at the 2015 VMAs, opting for an avant-garde ensemble that left little to the imagination, reminiscent of her “Wrecking Ball” music video attire. Sporting chandelier-inspired underwear and metallic suspenders, Cyrus dared to bare as she pushed the boundaries of fashion and body glue.
This daring look was just one in a series of revealing outfits she showcased that evening, including a completely transparent plastic dress adorned with strategically placed dots. While her risqué fashion choices undoubtedly turned heads, one can’t help but wonder about the practicality of such ensembles, especially in the potentially chilly auditorium. Nonetheless, Cyrus’s fearless approach to fashion continues to captivate audiences and solidify her reputation as a trendsetter in the entertainment industry.
Britney Spears, 2001
In the early 2000s, Britney Spears was determined to shed her bubblegum good girl image and embrace a more edgy style. When she arrived at the 2001 VMAs in a sheer number, fans were taken aback, wondering where the rest of her outfit was. The lace dress, which may seem tame by today’s standards, caused quite a scandal at the time, marking a departure from Spears’ previous fashion choices.
Little did fans know that Britney’s wardrobe would become even more revealing during her now-infamous performance of “I’m a Slave 4 U.” This bold fashion statement signaled a new chapter in Spears’ career, one defined by her willingness to push boundaries and challenge societal norms, both on and off the stage.
Lil Nas X, 2019
At the 2019 VMAs, Lil Nas X made a bold statement with his sparkling bullfighter-inspired outfit, blending elements of traditional matador attire with disco flair. The rapper donned a dazzling silver sequin suit, complete with lace accents and metallic heels, creating a look that was both eye-catching and memorable. What set his ensemble apart was his unique twist on the traditional tuxedo, opting for a cropped bolero jacket paired with matching silver pants.
This unconventional combination showcased Lil Nas X’s penchant for creativity and individuality, solidifying his reputation as a trendsetter in the music and fashion worlds. His outfit seamlessly blended elements of classic elegance with contemporary edge, making it one of the standout looks of the evening and further establishing Lil Nas X as a style icon to watch.
Rita Ora, 2018
In keeping with the sheer-dress trend, Rita Ora turned heads on the red carpet in a breathtaking Giuseppe Zanotti creation. While the singer jokingly attributed her choice of the revealing dress to the weather, there’s no denying the sheer elegance and artistry of her ensemble. The dress featured unique squiggly lines intricately embroidered onto the sheer fabric, strategically covering certain areas to prevent any wardrobe malfunctions.
This attention to detail transformed the gown into a true work of art, showcasing Rita Ora’s confidence and style. With its tasteful yet daring design, the dress perfectly embodied the mantra of “if you’ve got it, flaunt it,” allowing Ora to exude both grace and glamour on the red carpet.
Christina Aguilera, 2003
In 2003, at the VMAs, Christina Aguilera made a bold fashion statement with a flamboyant feathered dress. However, the choice of vibrant pink feathers proved to be more suited for flamingos than the red carpet. The attention-grabbing attire overshadowed Aguilera’s early 2000s-style pencil-thin eyebrows and frosted eyeshadow. The result? A distracting ensemble that left little room for appreciation of her overall look.
Those seated nearby likely endured the discomfort of feathers tickling them throughout the event. While Aguilera’s fashion risk showcased her penchant for daring choices, it missed the mark for elegance and sophistication expected on such a prestigious occasion. This sartorial misstep serves as a reminder that even celebrities aren’t immune to fashion faux pas, and sometimes, less is more when it comes to making a statement on the red carpet.
Paris Hilton, 2002
At the 2000 VMAs, Paris Hilton made a memorable entrance in an ensemble that raised eyebrows and sparked conversations. While the exact price tag of her outfit remains a mystery, it appeared as though she might have overpaid for what seemed like half a skirt and half a top. This unconventional choice featured the infamous “shark-bite” hem skirt, a trend many of us indulged in during that era.
Hilton’s pastel pink attire, complete with a coordinated tiny bag, epitomized the early 2000s fashion aesthetic. Despite the daring nature of her outfit, characterized by a diminutive halter top and an ultra-low-rise skirt (a staple of the era), it actually represented a relatively subdued look compared to her other fashion ventures captured by the paparazzi. Hilton’s bold style choices undoubtedly left a mark on the fashion landscape of the early 2000s, where experimentation and boundary-pushing reigned supreme.
Shakira, 2001
At the 2001 VMAs, Shakira showcased her signature blend of daring style and unique flair. Embracing her Colombian roots, she turned heads in a bold ensemble featuring an unconventional mix of leather and feathers. The outfit boasted lace-up, low-rise leather pants paired with a halter top crafted from bird feathers, a combination that might seem like a fashion faux pas on anyone else but somehow worked effortlessly for her.
While Shakira has since transitioned to a sleeker and more sophisticated aesthetic, many fans still fondly remember her earlier days of cowgirl-inspired looks and leather ensembles, particularly during the era of her hit song “Whenever, Wherever.” Despite her evolving style, Shakira’s ability to confidently rock even the most unconventional outfits remains a testament to her individuality and fearless approach to fashion.
Eve, 2000
At a red carpet event, Eve made a striking entrance in an ensemble that showcased her bold style and individuality. Sporting a fur shawl perfectly matched to her vibrant red hair, she effortlessly stood out from the crowd. While her red-accented outfit seamlessly blended with the carpet, it was her eye-catching metallic gold dress that truly commanded attention. The asymmetrical design, complemented by a thick jeweled choker, has surprisingly made a comeback in today’s fashion scene.
With her signature short red hair and undeniable confidence, Eve left a lasting impression, ensuring that no one questioned her identity as she strutted onto the red carpet. Her ability to effortlessly merge timeless elegance with contemporary trends solidifies her status as a fashion icon, leaving admirers in awe of her impeccable style choices.
