34 Memorable, Unusual Oscars Outfits That Didn't Quite Work

The ruffled silhouette of Kristin Wiig's dress sparked conversation among critics and fans alike. One Twitter user even went so far as to say that it looks like a "hot piece of lasagna." Hey, there are worse things, right?

The recent 2020 Golden Globes wasn't the first time Gwenyth donned a naked dress. The actress made jaws drop years before at the 2002 Oscars by going for this goth and braless look that had a lot of people talking.

Uma Thurman made a rare fashion blunder in 2004 with this billowing white dress that just looked like an arts-and-craft project gone wrong.

The custom white gown might have been gorgeous on its own, but many people were distracted by the red latex gloves.

It's probably one of the most iconic Oscars dresses of all time: The Icelandic singer made quite a statement at the 2001 Oscars by showing up in this swan-inspired number (and then literally laying eggs on the red carpet?!).

Back in 2010, Charlize Theron decided to step out on the Oscars red carpet in a Dior Couture satin gown that highlighted some very specific features. We'll just say that rosebud detailing should never be placed, uh ... in that area.

We're never opposed to a classic LBD, but St. Vincent's odd ensemble at the 2018 Academy Awards might just have been too little of a black dress. The singer wore a barely-there black minidress with an odd puffy sleeve and a unique hemline for the red carpet.

Kate could've pulled this off without the fringe cape and the updo, but combined together, the overall look was a bit of a fashion misstep, even for the 2000s.

This bizarre dress made out of American Express cards that Lizzy Gardiner chose to wear to the 1995 Oscars was definitely a statement piece — we're just not entirely sure what statement that was, exactly.

Props to Sarah Paulson for fully embracing the color pink at the 2019 Oscars, but this puffy, voluminous dress with a stomach cutout was a weirdly proportioned and a slightly over-the-top choice.

Actress Jennifer Connelly paired a drab dress with a super long scarf at the 2002 Oscars, and it didn't exactly work for the occasion.

We learned two things from this outfit that Demi Moore apparently fashioned herself: Never try to make your own DIY dress for the Oscars, and also, never ever pair bike shorts and a bustier top together.

This full-length purple dress that Nicole Kidman donned for the 1996 Academy Awards looked less like a chic Oscars gown and more like, well, a nightgown.

Maya Rudolph's full-length, loose-fitting red smock dress was an unusual choice for the 2018 Academy Awards, especially since it resembled the red carpet she was standing on.

Leave it to the one and only Cher to turn heads on the red carpet in a memorable outfit — this skin-baring embroidered ensemble (paired with a dramatic feathered headpiece, no less) was definitely the statement piece at the 1986 Oscars.

Hilary Swank looked more ready for the prom than the Oscars with this pale pink dress for the 2003 Academy Awards. Granted, it was the early 2000s, but the princessy pink tulle overlay was still a little too much.

Between all the extra fabric and the large bow detail at the waist, most viewers weren't entirely sold on this pale gold Gucci dress that Dakota Johnson chose to wear to the 2017 Academy Awards.

Kim Basinger took a note out of Demi Moore's book by designing her own Oscars gown the year after — and the result was equally out there.

An electric blue silk trouser suit was definitely a loud choice for Liza Minelli back in 2014, especially with the matching blue streak in her hair that came off a bit more garish than trendy.

Jennifer Hudson might have won the Oscar for Best Supporting Actress for her role in Dreamgirls, but her dress with a metallic snakeskin bolero jacket didn't get the same kind of love.