5 Celine Dion
Who can forget the weird backless silver tuxedo thing that crooner Celine Dion wore to the 1999 Oscars? Maybe it was Dior but come on people – the thing was hideous for any decade and any designer. It was shiny, white, and just all wrong. She even had a weird futuristic white fedora on her head to make the whole things more hideous. What was she thinking?
4 Kelly Osbourne
Now Ozzy’s daughter is a certifiable fashion expert, if you count being a red carpet commentator and co-host of Fashion Police being an expert. She’s got lavender colored hair but for the most part she looks pretty decent these days. A few years back though, she wore an outfit at an event that made her look like a tranny on one of John Water’s old movies like Cry Baby or Pink Flamingos. Her hair was in a 1950s bouffant flip with a big bow and she looked… pretty ridiculous. Seems like she’s matured out of these silly outfits, so the days of big bows and John Waters outfits might be behind her, hopefully.
Madonna isn’t afraid to take chances with fashion obviously, and she’s inspired some of the biggest fashion trends of the last few decades. Tutus, ankle boots, fishnets, neon. Still, she’s not twenty-five anymore and sometimes Madge will go off the deep end and show up in an outfit that would make other mothers her age scream in terror. For instance, take her “Oscar the Grouch” outfit that she wore to a Gucci event a while back — it seriously looked like Oscar and Peter Pan collided in the air, threw up on each other, and transformed into a mini dress. Add a gold belt, fishnet hose and some black and green lacy up shoes and, Ta-Da! Epic fail.
2 Paris Hilton
She’s usually running around in slut-tastic outfits and dancing on countertops and bars in Vegas and Ibiza, so it’s not hard to place Paris on a worst-dressed list. Unless of course you like mesh and hooker heels. At a 2003 red carpet event she wore a “dress” that would probably make a Playboy playmate embarrassed. The top was like a black bikini, the torso was see-through black mesh, and the teeny skirt (honestly it was more like a strip of fabric than a skirt, was Pepto-Bismol pink. She carried what looked like a big Pepto-pink trench coat with her too – a great match with her barely-there bikini dress ensemble. Classy.
1 Uma Thurman
Ok, usually she looks pretty decent, which isn’t saying much since most of the time Thurman is wearing bikinis and lounging on yachts in France or the Caribbean, but her dress at the 2004 Academy Awards was not at all a winner. It was frilly white and blue lace and she kind of resembled a Victoria’s Secret model in a pirate costume – not cute. It was kind of hippie meets couture and it was also kind of hideous. Her face looked gorgeous and she got to show off her long legs, but let’s hope she shelves this one far, far back in her closet.
So what’s your take on the worst celebrity fashions? Bjork’s swan dress? Johnny Depp and his layers of lame man jewelry? Let us know!