Oscars Fashion: 10 Of The Craziest Looks Ever!

Every year, our favorite stars put on their finest duds and walk the red carpet at Hollywood’s biggest awards show. But not all Oscars fashions are created equal—and every year, the looks run the gamut from sophisticated and exquisite to drab and dumpy. But while best- and worst-dressed lists are de rigueur during awards season, there’s always a celeb or two whose outfits defy such simplistic categorization—outfits that aren’t just good or bad, but remarkably odd. And in honor of the upcoming ceremony, we’ve put together a (by-no-means exhaustive) list of our favorite freaky fashions from Oscar shows past. Who looks like they got dressed in the dark? Who looks like they forgot to get dressed at all? Read on and find out!

Click on the image above to see our entire flipbook of all 10 crazy dressers!

Kate Winslet’s vine-entwined getup at the 1998 Oscars gave us a scare; we thought she was being eaten from the toes up by runaway vegetation. (It’s the matching shoes that did it.) But we’ve gotta give it to her: girl looks good in green.

Diablo Cody is an edgy screenwriter, not a shrinking starlet—and therefore free to go all-out in leopard-print chiffon and an up-to-there slit for her Best Screenplay win at the 2008 Oscars.

Everyone’s already piled on poor Jennifer Hudson for the Unfortunate Bolero Incident of 2007—so we won’t say it looked bad. (Even though it, y’know, kinda did.) But we will say that if Andre Leon Talley ever tries to deck her out again in such an unflattering, pointy-necked python accoutrement, she would be totally justified in punching him.

Halle Berry won the honors for Best Actress in 2002, but the daring dress she wore to the podium should also earn her an honorable mention for Most Creatively Covered Boobs.

If Cruella Deville, the Phantom of the Opera and the late Michael Jackson put their heads together for a dress design, the result would have probably been something a lot like Kim Basinger’s one-gloved structured ballgown from the 1990 ceremony—and everyone would have said it was GENIUS. (But since Kim designed this herself, everyone just made fun of her instead. Sad!)

Did Diane Kruger look fabulous at last year’s Oscars? Yes. And not least because her black-and-white tiered dress makes her look like an Oreo whipped cream cake.

It’s about time we got a dude in here, and nobody did it nuttier than Adam Duritz at the 2005 ceremony. The ruffled tux, the clashing patterns, the hair and… THE HAIR. But like Diablo, we’ll cut him some slack for being an artiste.

What happens if you give your red-carpet style over to five sugar-buzzed kindergartners and the Easter Bunny? Um…we don’t know! But it would probably look something like Faith Hill’s dress from the 2002 Oscars. (Unrelated: Is anyone else suddenly craving rainbow sherbet?)

In 2003, Hilary Swank donned a whimsical pink dress for the Academy Awards. Prediction: In 2053, she’ll admit that there was supposed to be a third part, and she just sort of forgot to put on the actual dress between her slip and the tulle overlay.

And finally… well, you knew it was coming: Though many have tried, nobody has ever, ever topped Björk’s strangling swan from the 2001 red carpet. Anatomically-correct couture? No one will ever bring The Crazy like this.

Who do you think had the craziest Oscar style? Vote in our poll below, and as always, if we forgot your favorite, tell us in the comments section!

Don’t forget to join MTV.com starting at 6 p.m. ET on Sunday for our two-hour Oscars red carpet live stream!