By: Awards Season 2013
-
1954
Fashion icon Audrey Hepburn won the Oscar for Best Actress for her role in “Roman Holiday” in 1954. The year’s ceremony was held in New York City, cementing the event in fashion history.
Photo Credit: NBCUniversal via Getty
-
1969
Barbra Streisand attended the 41st Annual Academy Awards wearing a see-through dress and a large bow that rivals Kris Jenner’s favorite out-there accessory.
Photo Credit: Ron Galella Collection via Getty
-
1986
Between the gigantic fluffy headpiece and her exposed stomach, Cher’s glitzy goth ensemble is the last thing one expects on the Oscars red carpet.
Photo Credit: Getty Images Entertainment
-
1987
Helena Bonham Carter is no stranger to looking a hot mess on the red carpet, but this black velvet and chiffon get-up coupled with her freshly rolled out of bed hair is a disaster that few can rival on the Academy Awards red carpet.
Photo Credit: Ron Galella Collection via Getty
-
1989
What’s worse? The cleavage, the gold, the patterns, or the biker shorts? There’s nothing else to say. There’s just too much going on.
Photo Credit: Ron Galella Collection via Getty
-
-
1998
Cher could’ve possibly pulled off this outfit at the 1998 Oscars were it not for the hat that looks as though it was picked up on the Vegas strip. What does Cher have against the people seated behind her? Is nobody seated behind Cher worthy of having a clear view of the ceremony?
Photo Credit: FilmMagic, Inc via Getty
-
1998
Madonna’s strategy of distracting us from her Addams Family wedding dress by shoving her bling in our face is smart, but ultimately unsuccessful.
Photo Credit: WireImage via Getty
-
1999
The fashion world has had a pretty major debate over this dress, but Gwyneth Paltrow's Ralph Lauren gown has gone down in history as one of the most iconic Oscars dresses ever.
Photo Credit: WireImage via Getty
-
2001
Did Faith Hill spill a child’s ice cream all over her dress or was it meant to look like it was tie-dyed by a 3rd grade class? Even the Kids Choice Awards would have a few things to say about this dress.
Photo Credit: Getty Images Entertainment
-
2001
There’s nothing else to say about Bjork’s swan with a snapped neck “dress” that she wore to the 2001 Academy Awards.
Photo Credit: SGranitz via Getty
-
2002
“You know what would make my tattered dress look even better? My window curtain!” Jennifer Connelly exclaimed as she shoved the makeshift scarf around her neck and ran out the door, grabbing a little girl’s purse on the way.
Photo Credit: WireImage via Getty
-
2002
We’ve been seeing a lot of Gwyneth Paltrow on this list, haven’t we? In an effort to outdo her tragic outfits of the past, she wore a see-through top this year. What will she do next?!
Photo Credit: Getty Images Entertainment
-
2003
Channeling Girls’ goody two shoes Shoshanna, Swank failed at pulling off the flowy and feminine dress
Photo Credit: WireImage via Getty
-
2004
Who let that limo driver onto the red carpet? Oh, wait. That’s Diane Keaton? Still, why did anybody let her on the red carpet looking like this?
Photo Credit: Getty Images Entertainment
-
2004
Angelina Jolie stuns in this pearl white dress that’s the perfect complement to her sultry and devilish personality.
Photo Credit: WireImage via Getty
-
2007
Cate Blanchett’s chainmail-like dress is good protection against everyone who was probably trying to claw at her in attempt at stealing this gorgeous dress.
Photo Credit: Getty Images Entertainment
-
2008
Did anybody expect Diablo Cody to wear anything less than loud and crazy and low-rent Kardashian-inspired fashion to the Oscars? Although her dress looks as though it was sewed together by Michael Cera on the set of Juno, her structured haircut and popping red lip halfway make up for the mess below her neck.
Photo Credit: Getty Images Entertainment
-
2009
Queen Beyonce stunned on the red carpet in 2009 and although her gold floral dress isn’t up to par with her current high-fashion wardrobe, she still managed to show the film industry who’s boss.
Photo Credit: Bloomberg via Getty
-
2002
Unlike Gwyneth, Halle knows how to rock the see-through top and wore one of the most iconic Oscar dresses in history to the 2002 Academy Awards. Florals cover her top and a deep burgundy rounds out the bottom creating a perfectly elegant look.
Photo Credit: WireImage via Getty
-
2010
Are you sure you wanted you wanted your breasts to look like swirls of icing on top of cupcakes, Charlize Theron? Not only that, but the rest of the dress is wrinkled as can be, making me wonder who’s to blame for this fashion disaster.
Photo Credit: Getty Images Entertainment
-
2010
From the hair, to the hoop earrings, to the red lipstick, to the stunning dress, not one bad thing can be said about Cameron Diaz’s perfect dress at the 2010 Academy Awards.
Photo Credit: Getty Images Entertainment
-
2011
I’m starting to think that Helena Bonham Carter is just having a big secret laugh at us.
Photo Credit: AFP via Getty
-
2012
The leg! The leg! The infamous leg! Angelina Jolie’s right leg poking out of her black dress instantly because the most famous leg on the planet and we’re huge fans.
Photo Credit: Getty Images Entertainment
-
2012
Is it see-through, is it nude, or is it tan? We’re not sure but Jennifer Lopez once again stuns us on the red carpet of the 2012 Academy Awards.
Photo Credit: WireImage via Getty
-
2012
Who better to round off our list of memorable Oscar fashions than Meryl Streep in this stunning sparkly dress that reminds everyone why she’s Queen.
Photo Credit: Getty Images Entertainment
-
2006
By going with one solid color, Michelle Williams kept the potentially kooky outfit from going overboard and turned it into a tasteful and classy piece.
Photo Credit: WireImage via Getty
-
2007
Penelope Cruz stuns at the 79th Annual Academy Awards in this simply elegant dress that also has the unintended side effect of making you want to curl up in its train and take a nap.
Photo Credit: Getty Images Entertainment
-
-
2008
Did anybody expect Diablo Cody to wear anything less than loud and crazy and low-rent Kardashian-inspired fashion to the Oscars? Although her dress looks as though it was sewed together by Michael Cera on the set of Juno, her structured haircut and popping red lip halfway make up for the mess below her neck.
Photo Credit: Getty Images Entertainment
-
2008
What can we say? Heid Klum looks like a beautiful human rose and looks divine from head to toe. It takes a true fashion superstar to one-up the movie stars at a movie awards event.
Photo Credit: WireImage via Getty
-
2009
Queen Beyonce stunned on the red carpet in 2009 and although her gold floral dress isn
-
2009
Anne Hathaway outshone the competition in this sparkly gown that blinded anyone who said a negative thing about her.
Photo Credit: Getty Images Entertainment
-
2010
Are you sure you wanted you wanted your breasts to look like swirls of icing on top of cupcakes, Charlize Theron? Not only that, but the rest of the dress is wrinkled as can be, making me wonder who
-
2010
From the hair, to the hoop earrings, to the red lipstick, to the stunning dress, not one bad thing can be said about Cameron Diaz
-
-
2012
The leg! The leg! The infamous leg! Angelina Jolie
-
2012
Is it see-through, is it nude, or is it tan? We
-
2012
Emma Stone arrived at the 2012 Academy Awards wearing a giant red bow that rivaled her head for dominance but thankfully Emma won and pulled off this amazing look even though the slight hint of red eye shadow is a bit too much.
Photo Credit: WireImage via Getty
-
2012
Sure, George Clooney is hot, but his date of the night, Stacy Keibler, stuns in her golden dress.
Photo Credit: WireImage via Getty
-
2012
Can we all just forget about that time Sacha Baron Cohen did his shtick and then poured fake ashes all over Ryan Seacrest? Moving on.
Photo Credit: AFP via Getty
-
2012
Who better to round off our list of memorable Oscar fashions than Meryl Streep in this stunning sparkly dress that reminds everyone why she
The Golden Globes and the SAG Awards have all been leading up to the biggest night in Hollywood: the Oscars! While the Grammy Awards were a nice distraction with some wacky outfits, the Academy Awards definitely bring out more refined, classy, and drop dead gorgeous style from the Hollywood stars walking the red carpet. At least, the celebs usually dress their best, although sometimes there are a few fashion faux pas, and we took a look at the most memorable Oscar fashions, be they good or bad.
Meryl Streep has always brought a classic glam to the Oscars, as has Anne Hathaway who not so long ago was a young Disney star. And while Jennifer Lopez always stuns with her sleek and sexy look, fellow singer Cher always misses the mark.
Click through the gallery above to see all the most memorable Oscar fashions ever!
Tune in Sunday, February 24th for coverage of the 85th Annual Academy Awards and follow us on Twitter @StyleList for our live-tweeting of the red carpet and ceremony!
More from StyleList:
The Best and Worst Dressed of the 2013 Golden Globes
Style Hits and Misses at the 19th Annual Screen Actors Guild Awards
Glitz at the Grammys: Best and Worst Fashion of All Time
The 55th Annual Grammy Awards Red Carpet Style
Photo Credit: Getty Images
Leading Ladies of the Oscars and their Award Winning Style
