Unless you’re really, really passionate about which film has the best sound effects editing, most of the fun of big awards shows is ogling celebs as they walk down the red carpet in dresses that cost more than your student loan debt and loaned jewelry worth more money than you’ll ever see in your life.
But as much fun as it is to gossip about how great all the stars look, it’s sometimes even more amusing to delight in their fashion fails. Whether they’ve over-accessorized, kept things too casual, or trusted a stylist with terrible taste, all of these celebrities have one thing in common: they’ve gone down in history as one of the 30 biggest red carpet style fails of all time. And if you’d prefer to laugh with celebrities, rather than at them, check out the 30 Funniest Awards Speech Acceptance Punchlines.
Cher has made waves a number of times on the red carpet, but the outfit she wore to the 1986 Oscars might be the worst of them all, thanks to the insane headdress she’s got on her head.
If you’re wondering why anyone would wear a dress like this to the Oscars, Faith Hill sang “Somewhere Over the Rainbow” at the awards ceremony that year. That still doesn’t make this epic fashion disaster okay, but it at least provides some context for what she may have been thinking. And for more laughs from country singers, check out the 30 Funniest Lines From Country Songs.
The meat dress Lady Gaga wore to the 2010 VMAs is the stuff of legend. The singer wore the dress to protest the military’s “don’t ask, don’t tell” policy. However, what dressing up in a dozen uncooked steaks had to do with service members staying in the closet is still unclear. And if you want to see the lighter side of Lady Gaga, check out The 30 Funniest Celebrity Pet Moments.
This very little number Madonna wore to the 2015 Grammys left little to the imagination. More specifically, the back of this piece of clothing is basically a sequined thong. And if you can’t believe how good she looks (outfit aside), Madonna’s Bizarre Anti-Aging Secret Will Blow Your Mind.
The 2015 Grammys were full of fashion mishaps. Case in point: singer Joy Villa showed up wearing a bunch of orange fencing.
Before Beyoncé was Queen Bey, she was still figuring out her look. This meant that, at the 2003 Vibe Awards, she was wearing this bizarre number, which upon close inspection is genie-esque pair of wide-leg pants.
Uma Thurman wore this Christian Lacroix-designed dress to the 2004 Oscars, and probably has regretted it ever since. Although she does deserve kudos for attempting the “fancy dirndl,” which does require a healthy amount of confidence. And to see what Uma does when she’s not on the red carpet or the big screen, discover these 30 Celebrities With Surprising Overseas Endorsement Deals.
Robert Downey, Jr.
The shiny suit, big turquoise bow tie, and sunglasses Robert Downey, Jr. wore to the 2010 Oscars would have been much better suited to somebody 30 years his junior. And if you’d like to see RDJ looking significantly better, check out 50 Amazing Over-40 Bodies.
Before she was a UN ambassador and role model, Angelina Jolie had a very weird goth phase. This included wearing this Morticia Addams-inspired outfit to the 2000 Oscars, where she also made out with her brother—all around a bad look.
You have to give Celine Dion credit. Not everyone would think to put a tux jacket on backwards and call it an outfit. But she did at the 1999 Oscars. And for even more ridiculous behavior from Dion, check out the 15 Most Lavish Celebrity Weddings of All Time.
Andra Day‘s outfit at the 2018 Academy Awards looked like she accidentally got trapped in a shabby chic duvet cover and decided to just go with it.
Billy Bob Thorton
The string tie is pretty bad, but it’s Billy Bob Thorton‘s ZZ Top hat that lets you know he really doesn’t care how he looks.
Barbra Streisand wore this sheer suit to the 1969 Oscars without realizing it was sheer, or so she claims. The see-through fabric is a confusing contrast with the demure oversized collar and bow.
Lizzy Gardiner wore this dress, made of expired American Express Gold Cards, to the 1995 Academy Awards, where she won an Oscar for Best Costume Design. Really.
Rihanna decided to switch things up from her usual racy attire at the 2015 Grammys. Instead, she dressed like an enormous strawberry marshmallow.
Nicki Minaj caught a lot of flak for her outfit at the 2012 Grammys, in part because she also brought a man dressed as the Pope along as an accessory. But looking back at the 2017 Met Gala, she may have been onto something.
Completely sheer dresses are sort of Victoria Hervey‘s thing on the red carpet, but this one has to be the absolute worst of them all.
Cameron Diaz wore this floral print Ungaro dress to the 2002 Academy Awards, along with a big turquoise bracelet. Unfortunately, she wound up looking like somebody’s aunt from New Mexico who just flew into town for a wedding.
The big bow on this dress turned what would have been a perfectly fine ensemble into something really, really bad. To make matters worse, there was another big bow on the back of Anne Hathaway‘s dress too, right under her butt.
Charlize Theron has had mixed luck wearing Dior to the Oscars, and the unfortunate placement of those roses definitely makes the dress she wore to the 2010 Oscars fall into the bad Dior category.
Juliette Binoche showed up to the 2001 Oscars looking like a goth flapper, with striped tights and haphazard pearl necklaces to round out the look.
Diane Keaton has long been known for her kooky sense of style. However, the vest, chain, hat, and gloves made her look like a time traveling hot air balloon salesman at the 2004 Oscars.
If Jared Leto was going for a look to help him stand out from the crowd, he certainly nailed it with the lavender tuxedo he wore to the 2015 Academy Awards. Unfortunately, not all attention is good attention, as he probably learned that night.
It’s hard to describe exactly what look Sally Kirkland was going for at the 2007 Oscars, but whatever it was matches this pose perfectly.
Pharrell tried something different at the 2014 Oscars and wore short pants to the event. As evidenced by this photo, this was clearly a mistake.
Some might say the animal print dress by Dior that Diablo Cody wore to the 2008 Oscars was too casual for a black tie event. Others might say that doesn’t really matter if you’re holding an Oscar in your hand.
Kate Hudson’s unfortunate lavender dress at the 2001 Oscars was definitely not helped out by her hair and makeup, which all colluded to turn her look for the night into a disaster.
Even a fashion icon like Tilda Swinton can’t get it right all the time, as evidenced by this black velvet sack with mismatched sleeves that she wore to the 2008 Oscars.
Sophia Loren showed up at the 2009 Academy Awards looking like Belle from Beauty and the Beast.
Of course, one of the most memorable red carpet looks of all time was worn by Bjork. People either loved her swan dress, complete with sheer body suit and bejeweled tights, or they thought she looked like an out of place figure skater. If it helps you decide, she also brought several ostrich eggs to the ceremony and dropped them on the red carpet. And if you want even more shenanigans from your favorite celebrities, check out the 30 Most Hilarious Celebrity Riders.
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