The MTV VMAs—which take place on Monday at Radio City Music Hall in New York—have always been a place for musicians to walk on the wild side as far as style goes. In the award show’s 24-year history, there have been plenty of memorable—and decidedly outrageous—fashion moments. Madonna set the tone at the very first show in 1984. She captured the world’s attention attention emerging from a 17-foot wedding cake wearing a bridal dress in her performance of “Like a Virgin.” The red carpet has played host to some equally impressive turns, with everyone from Beyoncé to Marilyn Manson making their mark in distinctive dress.
After their romantic getaway to Italy, Jennifer Lopez and Alex Rodriguez are back in New York City. The duo were spotted in midtown Manhattan earlier today dressed to the nines in slick tailoring (him) and a modern take on ladies-who-lunch (her, naturally). It’s not surprising given the pair’s predilection for polished couple style—Tuesday saw them coordinate in pinstripes and bold colors. Today’s approach was more subtle and lighter in palette, with Lopez and Rodriguez complementing each other in neutral tones.
For Lopez, this meant a tweed shift dress from Gucci which was infused with a dose of bling through chain link accents. That treatment was picked up on Lopez’s Chanel handbag, while retro-inspired aviators and pointy-toe stilettos finished the look.
Not to be outdone, Rodriguez brought a sense of swagger to the idea of a traditional tan suit. The all-star former Yankee slugger styled his with a light blue shirt and patterned tie. Clark Kent-inspired sunglasses and suede lace-up boots completed Rodriguez’s ensemble with gentlemanly flair.
Supermodel Cindy Crawford kept things cool in a Versace harness at the 1992 ceremony, paving the way for Mariah Carey’s leg-baring moment (1997) and Rose McGowan’s barely there dress (1998). The most outré and fabulous end of the VMA carpet? That award should probably go to Lil’ Kim for the glittering pasty confection she wore in 1999; though Lady Gaga’s Phantom of the Opera–inspired definitely comes in at a close second.
For more recent high-impact ensembles, look no further than Cher, who went in her signature sparkle by Bob Mackie in 2010; Katy Perry, who updated Britney and Justin’s double-denim look in Atelier Versace in 2014; and Beyoncé, who glided into the show wearing a feather-trimmed Francesco Scognamiglio in 2016 with her adorable daughter Blue Ivy in tow.
In anticipation of this year’s ceremony, a look back on some of the MTV VMA red carpet’s most outrageous style moments.