19 Of The Wildest Oscars Outfits In Fashion History

Sometimes, it’s not the Oscar winners who go down in history. When we look back at the Academy Awards, it’s sometimes the surprising things we remember like the actors who got snubbed or those cringe-worthy moments (ahem, Best Picture mix up from 2017). Another thing that leaves a lasting impression is the red carpet.

Those magical looks that make it onto the best-dressed lists are talked about for years, if not decades. That’s not to say that the worst looks are easily forgotten about. When award season rolls around, we often find ourselves wondering whether any daring celebrity will wear something as outrageous. It remains to be seen whether anyone will top these *crazy* looks at the 2018 Oscars, but it won’t be easy. These are the wildest Oscars outfits of all time.

19. Cher, 1986

It’s not just the red carpets of today that produce bold looks. Cher has one of the wildest looks in the history of the Academy Awards and it’s from way back in 1986. No one will probably ever forget this Bob Mackie creation given the size of it. How many times have you seen someone rock a showgirl-style headpiece on the red carpet? Exactly.

18. Cher, 1988

Yup, Cher makes it onto the list again. Just two years after stealing the show with that neck-hurting head piece, she was back in another bold Bob Mackie creation. This time, there was no elaborate head wear. To accept the Best Actress in a Leading Role Oscar for Moonstruck, she wore a risque black, erm, dress that didn’t leave a lot to the imagination. The cape helped provide some coverage in the back but not much. Even in today’s world of sheer dresses, this is still one wild, sexy number.

17. Jon Bon Jovi, 1992

No, your eyes aren’t playing tricks on you. That is in fact a purple crushed velvet suit and it is worn by Jon Bon Jovi. What also might shock you is that this photo is from the 1992 Academy Awards, not the 1982 awards. There are some throwback styles that still stand up today, but this look definitely doesn’t. Truth be told, it didn’t really hold up at the time. After all, it is purple crushed velvet in suit-form.

16. Geena Davis, 1992

Do your best to avoid looking at Jeff Goldblum‘s glorious mullet and take a look at what Geena Davis is wearing. She just scored an award for Best Actress for Thelma & Louise and the poor girl had to do it while wearing a big, puffy blue dress that looks like someone’s prom castaway. This is giving us some serious Cinderella vibes, and not in the good way. It’s a good thing that we cannot see the full dress because it actually gets worse.

15. Edy Williams, 1995

People might not be as familiar with Edy Williams as other actors and actresses on the list. She has a string of credits to her name from the 1960s in film and television, but she’s most infamous for showing up on the red carpet in over-the-top outfits. This one definitely fits the bill. You’re probably too distracted by the crystals attempting (and failing) to cover her nipples to realize she is also wearing a sequined dress backwards with the zipper completely open.

14. Sharon Stone, 1995

This outfit is from decades ago, yet Sharon Stone looks older here than she does now thanks to the matronly Mother of the Bride look. It’s hard to be believe that Sharon, queen of sexy, age-defying outfits, would wear something so dowdy and voluminous, but she did. Would you believe us if we told you that the actress is only 37 years old here? We’re not joking.

13. Woody Harrelson, 1997

Woody Harrelson is known for being a little out there, but normally he keeps it pretty tame on the red carpet. The big exception was this look. Long before his 2018 Best Supporting Actor nomination, the Hunger Games star turned up at the awards ceremony in a long black jacket and tiny sunglasses. Micro sunglasses might be a trendy accessory right now, but with the long jacket, he looks like he was from The Matrix…before The Matrix was even made. And just who is he holding hands with?

12. Celine Dion, 1999

It’s not just wild dresses that have gone down in history. Celine Dion’s white pantsuit at the 1999 Oscars was one for the books. We’re all for wanting to switch things up and experiment with silhouettes, but the key thing is it has to work out. This backwards jacket paired with the extreme fedora and oversized sunglasses did not. Who or what was the inspiration for this?

11. Björk, 2001

This one needs no introduction. Björk’s swan dress just might be the most famous of all the WTF dresses of all time. Can you imagine that she wore it 17 years ago and it’s still referenced? She showed up at the 2001 Academy Awards where she was nominated for Best Original song for “I’ve Seen It All” (Dancer in the Dark), and dresses and swans were no longer looked at in the same way from that moment forward.

10. Gwyneth Paltrow, 2002

There are a few questionable looks behind Gwyneth Paltrow in this picture, but they don’t quite distract from what she is wearing. The dress was very sheer and exposed just the hint of a nipple. It was so wildly different from the pretty pink dress she wore in 1999 when she won the Best Actress Academy Award for Shakespeare in Love that we were left wondering why the shift? Luckily, Gwyn has redeemed herself with outfits since.

9. Halle Berry, 2002

Halle Berry made history at the 2002 Academy Awards for becoming the first black woman to win the Oscar for Best Actress thanks to her work in Monster’s Ball. Her speech was very memorable, but so was her gown. The sexy style featured a sheer top with embroidered flowers carefully preserving her modesty. Combined with the heavy skirt, it was a surprising choice that remains one of the most memorable Oscars fashion moments 9 just not necessarily in a good way.

8. Sally Kirkland, 2002

What you are seeing is, in fact, an Academy Awards outfit. The head-turning look was worn by Sally Kirkland, who was previously nominated for the Best Actress Academy Award in 1998 for her work in Anna. It’s difficult to take this seriously given that it looks more like a costume than an awards season ensemble. And it’s obvious that she’s in on the joke, too. Just look at that pose. That is the confident pose of someone who is going to wear the look they want and give zero F’s about what anyone else thinks.

7. Uma Thurman, 2004

Let us clear one thing up: Uma Thurman did not wear a costume from Snow White onto the red carpet at the 2004 Oscars. This was actually considered a proper outfit. We can get on board with a romantic look, but not when it looks like it was taken straight from a story book or a renaissance fair. That blue bow was not a wise choice, either.

6. Diane Keaton, 2004

Diane Keaton has a style all of her own. Sometimes, it’s brilliant, while other times it has people saying, “WTF?” There were definitely a lot of Charlie Chaplin comments when she stepped out of the limo at the 2004 Oscars. She was nominated for the Best Actress Academy Award for Something’s Gotta Give. She didn’t win the prize, nor did she make it onto any best dressed lists.

5. Jennifer Hudson, 2007

Since her American Idol days, Jennifer Hudson has grown to become a fierce singing-acting diva with a major sense of style. Even the greats can have off days. That was largely the consensus with her 2007 Oscars look. She decided to pair her chocolate brown dress with a cropped silver jacket. It was futuristic, but not in the best way. And there were many Jetsons/alien references about it. People also wanted to know why she killed a perfectly nice dress with the random topper.

4. Charlize Theron, 2010

We’ve seen a lot of interesting ways for celebrities to show off their figures, but this was probably the first time that we’d ever seen someone wear a dress that enhanced their tatas with fabric sculptured into flowers. Charlize Theron is a glamazon who can pull off practically anything, but not even she could pull of these random flower boobs. It was a very hard sell.

3. Zoe Saldana, 2010

Holy great balls of purple, Batman. The 2010 Oscars had some outrageous looks. First we had Charlize, then we had Zoe Saldana. The dress was interesting with the mix of pale purple and sequins at the top… but then we got to the bottom. What was with those ruffles? Did the dress also function as a piñata? If that was the case, it would have made more sense.

2. Lady Gaga, 2015

There’s never a dull moment when Lady Gaga turns up on the red carpet. At the 2015 Academy Awards, many were surprised to see her take a traditional approach with a shimmering gown. Of course, she made it her own with her accessories. Many speculated whether she was scrubbing dishes and/or toilets before stepping out on the red carpet and simply forgot to take her rubber gloves off. We’ll never know the answer, but the look will still live on.

1. Jared Leto, 2015

Last but not least we have Jared Leto. The actor made the 2014 awards season interesting for men’s fashion because we never knew what he was going to wear. He returned at the 2015 Oscars to present the Best Supporting Actor award, and he wore what appeared to be a suit from a 1980s prom. Even when a dude wears a navy suit, it’s normally seen as a big deal so this powder blue suit — worn with blinding white accessories and a pink boutonniere — definitely won’t be forgotten any time in the near future.

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