actors jennifer lopez and sam worthington arrive on stage to announce picture

When Fashion Went Funky at the Oscars

The award for best dressed does not go to...


They say the greater the risk, the greater the reward. But sometimes the risk just doesn’t pay off — as you’ll see with these memorable Oscar ensembles of yore. (Pictured: Jennifer Lopez at the 2010 ceremony.)

Cher, 1986 Frank Trapper/Corbis via Getty Images Cher, 1986 Cher and costumer Bob Mackie’s 43-year working relationship yielded a wealth of jaw-dropping, eyebrow-raising designs. But none was so memorable as this black, midriffing-bearing number (complete with feathered headdress), which the singer counts as her favorite. "It made me feel like a queen," she said.
Kim Basinger, 1990 Ron Galella/WireImage Kim Basinger, 1990 Oscar winner and fashion designer? Sure. Basinger, a presenter at the 1990 ceremony, arrived in one of her own head-scratching creations—a voluminous white satin ball gown topped by an asymmetrical embroidered jacket. (And that lettering on her sleeve? It's "love" in Russian.) Whoopi Goldberg, 1993 KMazur/WireImage Whoopi Goldberg, 1993 Is it a jumpsuit? A dress? A...jumpdress? Critics had so many questions about this purple-green ensemble. Lizzy Gardiner, 1995 KMazur/WireImage Lizzy Gardiner, 1995 Don’t leave home without it! The “Adventures of Priscilla, Queen of the Desert” costumer attended the awards in a dress of her own design, composed of 254 expired American Express gold cards. The financial services company later purchased the gown from Gardiner, and it now resides in the National Gallery of Victoria, Melbourne.
Celine Dion, 1999 Jeffrey Mayer/WireImage Celine Dion, 1999 It was a little hard to tell whether the singer was coming or going in this backwards Galliano suit. Yet it’s a look Dion still defends: “If I would do this today it would work,” she recently told People. “It was avant-garde at the time.” Bjork, 2001 Vinnie Zuffante/Getty Images Bjork, 2001 Few Oscar frocks have raised critics’ hackles quite like this infamous swan dress worn by the Icelandic chanteuse. (Joan Rivers’ response: “This girl should be put into an asylum!”) Turns out, Bjork actually owned two of the Marjan Pejoski-designed dresses since they couldn’t be dry-cleaned. Faith Hill, 2002 SGranitz/WireImage Faith Hill, 2002 File this one under: taking a theme a little too far. For her appearance at the 2002 Academy Awards, where she performed “Somewhere Over the Rainbow,” the country singer opted for a rainbow sherbet gown from Versace.
Gwyneth Paltrow, 2002 S. Granitz/WireImage Gwyneth Paltrow, 2002 Typically pastel-pretty, Paltrow went over to the dark side for the 2002 Academy Awards, slinking about in a black Alexander McQueen dress with a sheer top that left little to the imagination. Uma Thurman, 2004 S. Granitz/WireImage Uma Thurman, 2004 With its blue sash and floofy sleeves, this Christian Lacroix had a bit of a Swiss Miss vibe to it. Diane Keaton, 2004 Vince Bucci/Getty Images Diane Keaton, 2004 The "Something’s Gotta Give" nominee was a real Dapper Diane in this three-piece suit from Ralph Lauren. Of course, Keaton is no stranger to menswear, but with gloves, boutonniere, handkerchief, and bowler, this was a whole lotta look.
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