Since the first Video Music Awards in 1984, MTV’s annual award show has brought together the best in entertainment for a night of music, dance, and, more often than not, unexpected moments. But in addition to shocking performances, its red carpet has offered an opportunity for celebrities to show off their wildest looks.
From Pamela Anderson’s unforgettable pink fur cowboy hat to Jennifer Lopez’s all white ensemble, the VMA’s have produced some of fashion’s most memorable moments. i-D takes a look at some of them:
Pamela Anderson
Pamela Anderson made red carpet history when she showed up to the 1999 MTV VMA’s dressed in sequined pants, a white lace bustier, and a larger-than-life furry pink cowboy hat. Nearly two decades later this iconic awards show look was recreated by no other than Kim Kardashian for Halloween in 2018. It is no surprise that Anderson’s past fashion choices are still replicated to this day as the Baywatch actress has been influencing the fashion industry and beyond for over three decades now. Known for her bombshell looks and ever-evolving style, Anderson has been the muse of many designers—for instance, she was the face of Vivienne Westwood’s SS17 campaign shot by renowned photographer Juergen Teller.
Lisa “Left Eye” Lopes and Lil’ Kim
Music icons Lisa “Left Eye” Lopes and Lil’ Kim posed for photos dressed in complementary sequined costumes while attending the MTV VMA’s in 1997. That night the two rappers also wore these outfits to perform a remix of Lil’ Kim’s hit song, “Not Tonight (Ladies Night Remix)” which featured other well-known artists such as Missy Elliott, Da Brat, and Angie Martinez. If Lopes’s outfit looks particularly familiar it is because some believe it was a source of inspiration for Beyonce’s 2015 Met Gala look which featured similar sequin and bead detailing.
Rose McGowan
Powerfully baring it all, actress Rose McGowan wore a totally see-through dress paired with a sparkly black thong while walking the 1998 VMA’s red carpet with then-boyfriend Marilyn Manson. Made up entirely of small, intricately threaded beads, the dress was not only a fashion statement but a political statement as well: McGowan stated years later during an interview that the ensemble’s purpose was to be a form of protest and a symbol of self-empowerment.
Missy Elliott
The iconic Missy Elliott put a spin on one of her most signature looks —a tracksuit—while attending the 2003 VMA’s. Dressed in a golf-inspired Adidas plaid suit with a matching cap and shoes, Elliott walked away that night with Best Video award for “Work It,” beating out Eminem, Johnny Cash, 50 Cent, and Justin Timberlake. She will be celebrated this year at the VMA’s once more as she is the recipient of the 2019 MTV VMA Video Vanguard Award.
Cyndi Lauper
Mismatched accessories, eccentric prints, loud colors, and unexpected detailing have all been the foundation of pop superstar Cyndi Lauper’s lauded style since she burst onto the airwaves nearly 40 years ago. In addition to her clothing, the native New Yorker’s hair and makeup, which has famously included neon dye jobs and brightly colored lipsticks, has also acted as an extension of her legendary image. Lauper was able to first develop her fashion sense years earlier while working at Screaming Mimi’s, a famous vintage shop on the Upper West Side of New York City. The shop, which has since moved to Manhattan’s East Village, is most known for their extensive selection of vintage clothing and accessories—including rare Gaultier from the 80s, and 90s Prada handbags.
David Bowie and Iman
When superstar model Iman and David Bowie arrived to the 1999 VMA’s they did not disappoint. Wearing a floral bustier gown paired with a beaded handbag, Iman was a vision of elegance, whereas Bowie exuded a certain air of cool in a pared down navy number with matching tinted glasses. Through the years, the creative duo had become known for their signature styles and one-in-a-million personalities: Iman often worked with Gianni Versace, Halston, and Calvin Klein, with designer Yves St. Laurent once famously referring to her as his “dream woman.” Bowie, on the other hand, continuously broke fashion boundaries through his stage costumes. Style stars seemed to have aligned when the powerhouse couple met years earlier after being introduced at a dinner party.
Prince
The inimitable Prince sat with wife, choreographer and dancer Mayte Garcia, in matching blue outfits while attending the 1999 MTV VMA’s at New York City’s Metropolitan Opera House. Prince, known as much for his gender-bending style as his music that has transcended time, often wore bedazzled blazers, frilled collars, heeled boots, and colorful suits, creating a fashion genre all his own. He would later take the stage later that night to introduce TLC before their performance of “No Scrubs.”
Madonna at the first ever VMAs
Madonna made headlines everywhere when she debuted her hit single “Like a Virgin” at the very first VMAs in 1984. During an appearance that made history, Madonna danced atop a larger-than-life wedding cake wearing a white lace bustier, armfuls of rubber bracelets, pearls, crucifixes, and her famous “Boy Toy” belt buckle. Her early style of the mid-80s was made possible in part by stylist and jewelry designer Maripol, who has also worked with other well-known artists such as Grace Jones, John-Michel Basquiat, Elton John, Debbie Harry, and Cher.
Jennifer Lopez
From sheer Versace dresses to Chanel ball gowns, Jennifer Lopez’s evolutionary style has checked off every box throughout the years. For the 2000 VMA’s Lopez proved she could pull off any outfit when she arrived in an all-white getup featuring a white bandana, white Sean John cropped top, a diamond chain link belt, and a nameplate necklace. The 2019 CFDA Fashion Icon Award recipient went on that evening to win Best Dance Video for “Waiting for Tonight.”