Gwen Stefani, Jennifer Lopez, And Madonna’s Original VMA Style Then And Now

Gwen Stefani at the MTV Video Music Awards in 2005 and 1998.
Photo: Getty Images

Considering it’s a total mishmash of some of the most creative stars in music, there’s no question the MTV Video Music Awards is pretty much a MECCA for originality. We’ve seen some seriously awesome outfits pass through the VMAs in the show’s 28-year-run, from Madonna’s “Like a Virgin” wedding gown to Lady Gaga’s meat dress and literally everything in between. Although we hate to play favorites, we’ve narrowed down the list of the most original VMA outfits over the two-plus decades…and noticed some repeat offenders along the way. Exhibit A: No Doubt frontwoman and fashion MVP Gwen Stefani, who manages to step out on a style limb every single appearance, and STILL looks amazing. Way back in 1998, she worked one of her most iconic outfits yet- a fuzzy blue bikini top, baggy pants under a skirt (!) and platform sandals. Oh hiiii ’90s! She also topped off all of this in Gwen S. staples, wild blue hair and a bindi… a look that’s been replicated by other red carpet originals over the years.

Gwen hit the VMAs one last time in 2005 before her hiatus, wearing a leopard print dress from her own L.A.M.B. collection. She looks gorgeously grownup, but just as original as she did back in the day.

Madonna at the MTV Video Music Awards in 2008 and 1984.
Photo: Getty Images

Madonna basically RADIATES originality, so we took a little 10-year-trip down fashion history lane to see how far Madge has come since the VMAs’ 1984 debut. For the star’s iconic (and controversial) “Like A Virgin” performance, she popped out of a giant wedding cake in -what else?- a poufy white wedding dress. let’s just say it definitely got people talking. She stirred the pot again in 2003, where she (ahem) bonded onstage with Britney Spears in a groom’s black suit and top hat. Wedding theme redux!

Jennifer Lopez at the MTV Video Music Awards in 2009 and 1998.
Photo: Getty Images

Jennifer Lopez has always brought her best fashion game to the Video Music Awards, starting off with her 1999 crop top-cowboy hat combo. It’s an unexpected mashup of Wild West and streetwear, but J.Lo pulls it off with swagger and a “come hither” side glance. She cranked up the glamour a decade later in a Louis Vuitton minidress and Christian Louboutin booties. Three stylish ladies, three outrageously awesome VMA outfits. There’s tons more where that came from in the photo gallery below, and stay tuned for even more crazy-cool fashion on September 6!


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