Vampires weren’t as popular back in 2000, but Jolie could have fit right in with them with this long black dress and almost equally long black hair. At least the night got a little brighter when she won best supporting actress for Girl, Interrupted. She then made headlines for kissing her brother, James Haven, on the mouth and declaring in her acceptance speech how "in love" with him she was.
The infamous swan dress worn by Bjork at the 2001 Oscars was as strange as the Icelandic singer herself. The Marjan Pejoski creation received awful reviews from most humans, but some birds gave it two wings up.
At 11 years old, the pint-sized Paquin won for her role in The Piano and accepted her statuette while wearing a crocheted headdress. But with age comes wisdom, and a better understanding of socially acceptable Oscar attire.
The Sister Act actress went neon when she hosted the 1993 Oscars. While the coat may have been a deep purple from the outside, Whoopi Goldberg didn’t miss the chance to open up the jacket and reveal not only a neon green lining, but also outrageously patterned pants.
This Emmanuel Ungaro gown that Diaz wore in 2002 looked like a robe to many, and the purple belt was a mystery accessory that just didn’t work. "I wanted to wear something I felt casual and myself in," she told People magazine. "I feel like I just got out of bed and threw it on." And with the messy hairdo, it looked like it, too.
Keeping with the suit trend, the singer wore this all-white ensemble to the Oscars in 1999. With pants that looked two sizes too big and a coat that appeared to be on backwards, many didn’t know what to think about the outfit from the Canadian crooner.
The naturally beautiful Bejo wore a pale mint Elie Saab gown to the 2012 Oscars, where she was nominated for her role in The Artist. The understated dress clashes with the actress's extreme hair color.
It was a toss-up whether Theron had roses or cinnamon buns covering her chest at the 2010 Academy Awards. This Dior gown looked great from the sides, but when Theron faced the camera, all attention was directed to those roses. Or cinnamon buns.
There is nothing right about this look from 1988 when Cher took home her best actress award for Moonstruck. If the sheerness of the Bob Mackie creation weren’t enough, check out that extra-long scarf.
Theron makes the list again with this shoulder-heavy Galliano for Dior gown in 2006. With its green tint and bow accents, she looked more like a present than a presenter at that year’s Academy Awards.
After wearing the Bob Mackie beaded headpiece to the 1998 Oscars, the If I Could Turn Back Time singer might have wished she could do just that.
With the writer's outrageous personality, it probably wasn’t a surprise that she wore this Christian Dior animal print dress in 2008. That night, Cody took home the Academy Award for best original screenplay for Juno.
This number from 2004 isn’t even a dress, but it’s still one of the worst Oscar outfits to show up in the carpet. Keaton wore this Ralph Lauren suit when she was nominated for best actress in Something’s Gotta Give, but many wondered if she was reverting back to her Annie Hall days.
On the red carpet in 2002, the country star looked less like a celebrity and more like a marshmallow pulled from a box of Lucky Charms.
All the Shakespeare in Love best actress winner was missing with this outfit was her corsage. At the 1999 Oscars, Paltrow chose this ill-fitting gown that looked like a prom dress and could fall down at any moment.
This time, it looked like Paltrow decided to pass on both a stylist and a bra at the Academy Awards in 2002. The goth Alexander McQueen outfit was sheer on top, revealing more of herself than she may have wanted to.
Swank wore this pale pink, sheer Dior gown to the 2003 Oscars, but pink taffeta should be strictly reserved for special events, like junior prom.
Connelly's gold, obscenely long scarf may have matched her best supporting actress Oscar, which she won for A Beautiful Mind, but it did not match the Nicolas Ghesquiere for Balenciaga dress.
The beautiful, brown, pocketed Oscar de la Renta dress that Hudson wore to the 2007 Oscars looked great later in the night when she ditched the bolero and accepted the award for best supporting actress for Dreamgirls. But on the red carpet, the metallic snakeskin blazer brought a weird, space-themed vibe to the outfit.
What Lopez lacked in sleeves, she made up for in cleavage. The Zuhair Murad gown that she wore in 2012 featured shoulder cut-outs and a very low neckline.
The Armani gown that J.Lo wore to the 2010 Oscars had enough extra material to last the ex-American Idol judge all awards season.
This much velvet should not be allowed in a single outfit. Binoche won best supporting actress for her role in The English Patient but won little praise for her Sophie Sitbon gown.
Nominated for her role in Almost Famous, Hudson paired her 2001 Stella McCartney fringe dress with a messy, curly updo, neither of which was particularly flattering.
Between J.Lo's gown and this ensemble, 2012 was a tough year for sleeves. Mara's ill-fitting Ellie Saab gown sported floral embellishments and one droopy sleeve.
The Sense and Sensibility star wore this Pepto-Bismol pink gown on the 1996 red carpet, which marked her first appearance at the awards show.
Gardiner wore a dress made out of American Express Gold Cards to the 1995 Oscars. This dress was clearly supposed to make a statement; it is just unclear what that may be.
After putting on her Francesco Scognamiglio fur vest and fishnets, the Material Girl singer was running late for the Vanity Fair Oscar party and dashed out of the house forgetting something very important — her pants.
The pop star opted for an Asian-inspired look for the 1999 Oscars in this oversized two-piece outfit.
Most celebrities opt to accessorize with jewelry, but in 2005 Griffith choose to complement her Atelier Versace gown with a leg cast and walking cane (designer unknown).
The Bridesmaids star wore the Marina Rinaldi gown to the 2012 awards show, where she was nominated for best supporting actress. The unappealing, dust-brown color does not flatter the funny lady.
With 17 Academy Award nominations, Streep is no stranger to the Oscar red carpet, but her 2012 frumpy, gold gown and matching belt was a novice fashion mistake.
The Dior gown that Kidman wore to the 2011 Oscars received mixed reviews. Some loved the style of the dress, while others claimed it made her hips look larger than they actually are.
Sesame Street's Count Von Count was clearly the inspiration for Kirkland's 2007 Oscars outfit, which featured a Technicolor vampire cape.
The actress' Sex and The City character, Carrie Bradshaw, was known for her eccentric style, but at the 2010 Oscars art imitated reality when Parker showed up to the red carpet wearing a bizarre, shapeless Chanel frock and a 1960s hairstyle.
At the 2002 Academy Awards, Blair left little to the imagination in this red Versace dress. While she wasn’t nominated for anything that year, she definitely takes home the award for most tassels at the Oscars.
In 2009, the Italian actress dressed in a yellow Armani complete with a plethora of nauseating swirls.
Sarandon won a 1996 Oscar for Dead Man Walking but would not be receiving any "Best Dressed" awards for her brown, satin dress.
In this jarring orange frock, the Hustle and Flow actress made sure that she stood out against the multitude of other celebrities on the red carpet in 2005.
In 2008, Swinton decided to wear a one-armed Snuggie to the Oscars. The Lanvin gown looked almost like it was made out of garbage bags, especially in the light when Swinton won best supporting actress for her work in Michael Clayton.
At the 2000 Academy Awards, the South Park creators dressed in drag, with Stone and Parker parodying Jennifer Lopez's scandalous, Versace scarf dress from the 2000 Grammys and the gown Gwyneth Paltrow wore in 1999 when she accepted her Oscar for Shakespeare in Love.
The actress dipped back into her Swedish roots with this Heidi-like dress in 2004.
In 1996, the former Playboy playmate wore a green velour dress accented with a jeweled, star broach.
Crimped hair should never be worn in public, especially not on the red carpet, but no one seemed to inform the Prince of Tides star, who paired the unfashionable hairdo with an equally cringe-worthy mauve cape.
In an attempt to design her own dress, Demi Moore came up with this ensemble for the Academy Awards in 1989. With biker shorts and a bustier top, maybe Moore should have stuck with professional designers.
At the 1992 Oscars, actress Geena Davis, in a dress by costumes designers Ruth Meyers and Bill Hargate, looked like a runaway bride that left the bottom half of her dress at the wedding reception.
Graham wore this floor-length leather dress to the 1999 Academy Awards. It makes a person think — how many cows had to give their lives to make this unfortunate gown?
In 1989, Foster won an Oscar for her leading role in The Accused. She accepted the award in an ill-fitting aquamarine cocktail dress, which she paired with white tights.
Another star to take a stab at designing her own Oscar dress was Kim Basinger in 1990. The half-dress/half-jacket look mixed with the missing shoulder and extra-long glove combined to make this one of the worst Oscar outfits in history.
To promote his new film The Dictator, Cohen showed up to the 2012 ceremony in character wearing "John Galliano and Kmart socks." He accessorized with Kim Jong-il's "ashes" that he carried in a golden urn.
The French film editor opted for "garbage-bag chic" at the 2012 Oscars. That night she was nominated for her work on The Artist.