30 Oscars Outfits That Will Make You Wonder What The Hell They Were Thinking

The Oscars. We tend to watch them for two reasons. One, we want to know who wins what for the acting categories as well as a picture of the year - every other category is meh. And two, we watch the Oscars for the fashion. Nothing tops the red carpet walk where we get to see our favorite A-listers parade down the red carpet in the latest, most daring fashion creations. Now, Oscar season is right around the corner, we're going to take a little trip down memory lane to look back at some of the outfits that still stick in our minds - the good, the bad, and the ugly.

[post_page_title]#1 Bjork[/post_page_title]

Worn to the 73rd Academy Awards, who can forget about this dress? It's so horrendous! But it's also so iconic, having been parodied and referenced since. The Icelandic singer Bjork has always had a quirky sense of style, but this one might be the weirdest one yet.

No wonder the swan dress still sticks out in our minds. While the whole point of the dress attire for the evening is to bring elegance and glamour, nothing disrupts that quite like showing up like an extra in a high school production of Swan Lake. It is definitely one that will be going in the history books for sure.

[post_page_title]#2 Billy Porter[/post_page_title]

"Yaaaas Queen! Werk!" You could almost hear it as Billy Porter strutted the red carpet at the 91st Academy Awards wearing this Christian Siriano gown. At a time, when gender identity and gender role constructs are being challenged and questioned, Porter - the star of the hit TV show Pose - threw the gender roles of clothing out the window.

Not only was his choice a very politically charged statement towards inclusivity and acceptance, but it was also a very personal choice for the actor who revealed that he'd always wanted to wear a ballgown himself.
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[post_page_title]#3 Jennifer Lopez[/post_page_title]

Never a stranger to the red carpet, actress and singer Jennifer Lopez has given us many memorable red carpet looks throughout the years. This one is one of her most iconic Oscars looks since it was so unexpected.

But she proved that taking a fashion risk sometimes pays off for the better. No wonder she usually always makes the best-dressed list of the Oscars. This mint-green one-shoulder dress was an absolute dream on her!
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[post_page_title]#4 Hilary Swank[/post_page_title]

Beautiful dress. It's been years since Hilary Swank was walking the red carpet as a nominee - and then subsequent winner - for the 2005 film Million Dollar Baby, and we still remember this dress.

The look was everything. The color was fantastic. The open back was daring. The styling lines were perfect. The dress was absolutely beautiful. B-E-A-U-T-I-F-U-L!
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[post_page_title]#5 Keira Knightly[/post_page_title]

While she may not have won the award Best Actress for her nomination of her portrayal as feisty Elizabeth Bennett in the film adaptation of Pride and Prejudice, but she was definitely a winner on the red carpet.

Her dress was stunning, and the necklace that accompanied it was the perfect touch. She definitely deserved her spot on the best-dressed list that year.
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[post_page_title]#6 Rita Moreno[/post_page_title]

This Hollywood legend has been in the industry for decades! And last year at the 2018 Academy Awards, she pulled something memorable that we'll remember for a long time: she recycled the same dress that she wore to the 1962 Academy Awards.

Talk about an iconic recycle. That means that her gown was hanging in her closet for 56 years! Wow! And she looks just as stunning in her gown as she did when she first wore it, proving that she has aged like a fine wine.
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[post_page_title]#7 Lupita Nyong'o[/post_page_title]

In 2014, this actress snagged the Academy Award for Best Supporting Actress for her role in the film 12 Years A Slave. In addition to the rise in fame she received from this breakout role, she also received attention for her sense of style.

At the awards ceremony, all eyes were on her as she walked the red carpet in this ethereal blue number. It was feminine, it was delicate and just oh-so-beautiful. And her lightly feminine accessories were the perfect touch. The only other thing that could make her dress look better was the Oscar statue that she went on to win later that evening.
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[post_page_title]#8 Lady Gaga[/post_page_title]

Remember the days when Lady Gaga used to show up to red carpet events in a meat dress or getting carried in by porters in an egg? Yeah, me too. But I am so glad that since then, she has kind of traded in the avant-garde fashion statement pieces for more classic lines.

And she is nailing them. This white number that she wore to 88th Academy Awards was created by designer Brandon Maxwell. It was a dress/pantsuit combination all in one. It was definitely a clever mix of the avant-garde Gaga that we all recognize plus the glamorous Gaga that we've come to discover was in there all along.
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[post_page_title]#9 Diane Keaton[/post_page_title]

Long before Billy Porter came along to play with gender on the red carpet, there was Diane Keaton. Back in 2004, this kooky actress puzzled the red carpet when she showed up wearing a very dapper menswear suit.

While at the time Keaton made all the worst-dressed lists, over the years, this look has come to become an iconic memory. It proves that women of any age can look hot in suits. Personally, I would!
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[post_page_title]#10 Celine Dion[/post_page_title]

Celine Dion's look has since become an iconic look of Oscar ceremonies past. At the time, it was put onto the worst-dressed list. But looking back, it's quite an interesting choice.

Celine Dion definitely proved that she didn't care what others thought about what she was wearing, she just wanted to have fun on the red carpet. And to be honest, it definitely looks like the more comfortable choice as opposed to a big poofy ballgown.
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[post_page_title]#11 Angelia Jolie[/post_page_title]

An A-list celebrity for a while, Angelia Jolie is no stranger to serving up amazing looks. She has also been somewhat of a sex symbol, so it's not surprising that some of those looks she gives us have a subtle sauciness to them.

And this Academy Awards look from 2012 is no exception. She looks elegant, yet is giving us legs for days. It's an iconic look, and there is no doubt that it is a sexy, dark look that Maleficent would approve of and wear.
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[post_page_title]#12 Charlize Theron[/post_page_title]

Long before the great debate of blue versus gold dress, there was roses versus cinnamon rolls on Charlize Theron's 2010 Oscar dress. Normally a leading fashionista on whatever red carpet she walks, Theron sort of dropped the ball on this one.

She made the worst-dressed list that year for her dress, but still, it has become somewhat iconic. The color is very pretty on the actress, but the styling was not so good. Especially given that the chest area is covered with weird fabric cinnamon rolls.
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[post_page_title]#13 Marion Cotillard[/post_page_title]

Back in 2008, Marion Cotillard won for Best Actress at the Academy Awards. She also graced us with this iconic white gown. It's as if a mermaid came out of the sea to walk the red carpet.

With the upcoming live-action remake of Disney's The Little Mermaid, can I please suggest that the costume designers revisit this iconic Oscars look for inspiration? I have no doubt that it's a gown that would look great on Ariel at the end of the film. Just saying.
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[post_page_title]#14 Halle Berry[/post_page_title]

The 2002 Oscars were a night for firsts. Halle Berry broke ground in being the first African American woman to win the category of Best Actress, earning the accolade for her role in Monster's Ball.

She also stunned on the red carpet. This dress with the burgundy bottom and the lace top with the flowers strategically placed ended up staying with us for years. Truly an iconic piece of couture.
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[post_page_title]#15 Gwyneth Paltrow[/post_page_title]

She might not have been nominated for anything that year in 2012, but nonetheless, Gwyneth stunned on the red carpet with her Tom Ford capped gown. It was classic and clean lines, yet had an almost masculine and structured look to it.

Can't say that we remembered any other gowns on that red carpet as much as we remembered that one. It was a classic. And the white was so complimentary. Many people underestimate the elegance of white.
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[post_page_title]#16 Penelope Cruz[/post_page_title]

Cruz wore this peach number to the 79th Annual Academy Awards, and it was incredible. She looked gorgeous. Everything was perfect.

The peach hue was the perfect compliment to her bronze skin, plus her hair and makeup were subtly elegant. Everything about this look gave us life.
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[post_page_title]#17 Michelle Williams[/post_page_title]

Can anyone forget this look? No, they can't, that is why this look has been so iconic. Michelle Williams wowed the world when she stepped out onto the red carpet with this beautiful saffron yellow gown by Vera Wang.

It was definitely a bold color choice, but the actress pulled it off. It was absolutely fantastic. We will be much more open to this color choice in future thanks to Michelle Williams' perfect execution.
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[post_page_title]#18 Sharon Stone[/post_page_title]

Oh, the 90s. It was an era of fashion... choices. And nothing highlights this quite like the 1998 Academy Awards when Sharon Stone rocked up wearing a Vera Wang skirt that she paired with a white shirt from the Gap.

The actress's fashion choices from that year have become infamous in the years to come, mostly because it was such a bad idea. The look is a bit sloppy, almost like she was showing up to a fancy event following a one-night stand.
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[post_page_title]#19 Cate Blanchett[/post_page_title]

Cate showed up to the 88th Academy Awards wearing this blue floral number. The color looked absolutely incredible on the actress.

Cate has always been a stunner on the red carpet. But this look made us all envious that she got to wear that dress and we didn't.
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[post_page_title]#20 Nicole Kidman[/post_page_title]

A veteran of the red carpet, Nicole Kidman definitely knows how to bring a beautiful look to the red carpet. In 2007, she wowed in a red Balenciaga gown.

There is no denying that the red carpet got upstaged by Kidman that night. What a wonderful red gown.
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[post_page_title]#21 Salma Hayek[/post_page_title]

The beautiful Mexican actress is always a red carpet favorite. She pulls off outfits that others sometimes can't. And this 2013 Oscars look was simple yet so elegant on her.

And the beehive inspired hairdo definitely helped to pull her hair up so she could show off the incredible gold detailing of her black gown. So pretty!
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[post_page_title]#22 Ashley Judd[/post_page_title]

Sometimes simplicity is best. This gown that Ashley Judd wore to the Oscars was simple, yet brought such a wow factor with it.

The color stole the show, and she did right by accessorizing it with simple jewelry and lightly waved hair. It was everything that we wish we could wear to an award show.
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[post_page_title]#23 Uma Therman[/post_page_title]

When you gotta go to an award show at 7 pm, then pull pints at the renaissance fair at 8 pm. That is what Uma Therman's dress from the 76th Academy Awards in 2004 was conveyed to us. Normally a red carpet crowd-pleaser, Uma's fashion misstep has not been forgotten.

This Christian Lacroix wasn't the best choice for both actress and designer alike. We won't be forgetting the horror of that fashion faux pas any time soon.
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[post_page_title]#24 Reese Witherspoon[/post_page_title]

America's favorite sweetheart has given us many beautiful red carpet looks over the years. This is one of our favorites, and is a standout in terms of her red carpet fashion. She wore it to the 2011 Oscars.

The simple black gown had clean lines, plus a little hint of white at the top neckline. She gave the look an almost retro, Bridgette Bardot-inspired vibe with her updo. And the emerald earrings were the perfect little pop of color.
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[post_page_title]#25 Linda Cardellini[/post_page_title]

Clearly, Linda Cardellini took a page out of Miss Vanjie's season 10 playbook. This loofa-inspired gown was way too frilly. To add insult to injury, the color was exactly what many bath product companies use when creating their loofas.

It was definitely not a good choice for the actress. And there is no way that we will be forgetting it any time soon. I mean, if you Google "worst-dressed Oscars all time" this one already pops up. Oops!
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[post_page_title]#26 Demi Moore[/post_page_title]

The 80s was another era of fashion... choices. And the 1989 Academy Awards gave us this iconically bad outfit worn by Demi Moore. She is a natural beauty, but even her looks couldn't salvage this spin class inspired outfit that looked like she pinned a curtain to bicycle shorts.

Like other worst-dressed list outfits, this ranks as one of those that will stick with us for years to come. Oh, the horror.
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[post_page_title]#27 Jennifer Lawrence[/post_page_title]

Perhaps the only thing more iconic than J-Law's fall at the 2013 Oscar's, was her pale pink Dior gown. The feminine gown was absolutely incredible and a total treat for the eyes.

Not only was she a winner on the red carpet, she was also a winner that year as well, bagging her first Oscar at 23 years old. Not a bad way to start your acting career. We've forgotten about her fall up to the stage - well, sort of. But there is no way we are going to be forgetting this classic Dior gown anytime soon.
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[post_page_title]#28 Gemma Chan[/post_page_title]

Crazy Rich Asians star Gemma Chan arrived in a hot pink tent to the 91st Academy Awards. Some called it fashion, some called it a faux pas. But at least the dress came with pockets.

We call it something that's going to go down in Oscar fashion history. It certainly isn't something that will be forgotten any time soon. Everyone remembers a good fashion debate.
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[post_page_title]#29 Emma Stone[/post_page_title]

Always an elegant starlet on the red carpet, Emma Stone brought the glamor to the 2012 Oscars red carpet. When an actress or actor chooses to wear red, it's always a bold move.

I mean, the red carpet is called the red carpet because it's red. When not done well, the red carpet wins. When executed beautifully, the red carpet loses. And the red carpet lost to Emma Stone that night. Simply stunning.
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[post_page_title]#30 Awkwafina[/post_page_title]

Another star of Crazy Rich Asians is Awkwafina. The same year that Billy Porter took the red carpet by storm also saw Awkwafina play with traditional gender silhouettes. This actress and rapper took a dare and wore a DSquared pantsuit to the awards ceremony occasion.

While many people didn't like it, and she was placed on the worst-dressed list, it was still a bold move to go against what is expected to be worn. Much like Celine Dion and Diane Keaton, this pantsuit won't lightly be forgotten any time soon.