Red Carpet Fails: The Worst Oscar Dresses of All Time

We get it — Kristen Wiig is a funny lady — but her dress shouldn't be the punchline. The gloves give the look a true crime feel and the shoes are confusing. It's an uncomfortable-looking outfit, let's be honest.

With a circa late 90's and/or early 2000's vibe, this black tassels and pale pink dress misses all the marks. Nothing is especially flattering and nothing feels right when looking at it.

From the awkward drop of her dress to the uncomfortable neckline, this dress would have failed in 1963, 1974 and any year Lea tried to wear it.

Look, we get that she's always trying to be fashion-forward with her choices, but good golly, this shiny rubber rain slicker capelet and flowery pleated skirt are almost unforgivable. (Not totally, because we still love her, but damn close).

For most of awards season 2019, Cardellini played it safe. Nothing too boring, yet nothing super exciting either. Then she must've lost a bet for Oscar night and was forced to wear the loudest, angriest dress she could find. Yes, "angry" isn't typically used to describe a garment, but this one is clearly swallowing her whole and once done, plans to hunt down its next victim.

This is the baby version of Linda Cardellini's dress. And those tiers and shoulders definitely look stabby.

Rewind back to the early 2000s when this look was just as ew as it is today. The singer's rainbow gown hit all the wrong notes.

Sure, it was the '80s, but that's still no excuse for bicycle shorts and an embroidered corset top with peekaboo bra. If it weren't for all the metallic features, we would've totally believed she stole this from Elvira's closet.

The bustier and ruffled bubble skirt/train combo, with the black spaghetti straps and hosiery and the long white gloves made this outfit an all-around doozy. Oh, the '90s.

In 2018, St. Vincent stepped out in a downright wacky LBD. Though we hand it to her for testing out a much bolder choice than the long, embellished gowns nearly everyone else opted for, we can't help but wonder if the huge single puffy sleeve is supposed to be making up for the missing bottom half of her dress?!

We're not sure if we should blame Oscar-winning diva, Cher or Bob Mackie for designing this sartorial nightmare. Bared belly buttons and fake hair are two things that should never make their way onto the red carpet, unless it's on Halloween!

Singer Andra Day served up an over-the-top floral print getup you simply could not miss on the red carpet. The drop-crotch makes it look more like a pantsuit rather than an Oscar-worthy dress (with the bizarre seam placements leaving us scratching our heads). She looked like she was swimming in it! Her whole look was extra (and not in a good way).

This sparkly lavender pleated number was a questionable choice for the 90th Academy Awards. From the colour and cut to the chain detail spread across her chest, it was a total fashion flop for Salma Hayek last year, who doesn't need this much embellishment to look glam.

Poor Kim Basinger probably thought she looked edgy when she strolled across the stage at the 62nd Academy Awards. She claims to have designed the horrific Jekyll-and-Hyde-like wedding dress herself.

Repeat offender Cher graced the red carpet again in 1998 wearing another Bob Mackie creation. Though we'll admit, the dress had some redeeming qualities – cape aside – we just couldn't get on board with the frilly visor or lace choker.

We've seen her wear her fair share of over-the-top looks over the years, but who could forget the backwards tuxedo jacket Celine Dion sported in 1999 when she was nominated for Best Original Song for "The Prayer" (from the animated film Quest for Camelot)? Sure, it's not technically a dress but had we known this was the outfit she was going to choose, we would have hoped for rain or some sort of spill that would have prevented her from actually wearing this to the show.

Probably one of the most memorable Oscar dresses (for all the wrong reasons), Bjork's swan dress is still making appearances at Halloween parties.

Angelina Jolie has come a long way since she arrived at the 72nd Academy Awards looking like a gothic princess. Pair this with the awkward make-out session she had with her brother and we'll agree that this was a red carpet mishap we're happy to forget.

These days, it's pretty rare to see Gwyneth Paltrow take a red carpet fashion misstep, but in 2002 her gauzy tank with no bra and massive taffeta skirt was doing her no favours.

We struggled with including this lilac Dior dress Charlize Theron wore to the 82nd Academy Awards in 2010. We didn't think it was possible for Dior to do wrong, but rose buds should never be applied to boobs – or anywhere, for that matter!

Clearly, retired professional wrestler Stacy Keibler learned nothing from Charlize Theron's faux pas. Even George Clooney couldn't distract us from the massive gold rose coiled on the hip of her Marchesa gown that made her look twice her size.

Many people claimed that Halle Berry was the best-dressed actress on the red carpet at the 74th Academy Awards. We beg to differ. Even Elie Saab couldn't make us fall in love with this hip-enhancing mermaid skirt, over a floral sheer bodysuit, reminiscent of retirement home rugs.

No one is debating whether Uma Thurman is beautiful enough to be a Grecian goddess, but that doesn't mean she needed to dress like one. Sorry Uma, but Christian Lacroix really let you down this time.

It's impossible to ignore (or forget) Anne Hathaway's 2007 Oscar dress: the year of the bow! As if the oversized boob bow wasn't enough, there's another one on the back of the dress just below her rear.

To say that Tilda Swinton has a unique sense of style would be an understatement. The woman does androgyny like nobody's business – which is fine with us! What isn't fine is this lumpy, velvet sack she wore to the ceremony in 2008.

No one would ever call Whoopi Goldberg a trendsetter. It's not that we're trying to be mean, but this outfit is just one of many fashion blunders we have spotted over the years.