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The 6 Most Ugliest Dresses of All Time...

It’s holiday party season, and the “ugly Christmas sweater” joke is getting old! Everyone and their mother’s boss is gluing ornaments and lights to their chest, and I’m no longer laughing. Where are the gowns and the cocktail dresses? The true rebels of this season are the ladies who spurn the socially acceptable gaudiness and really get dressed up. I’m talking about ugly Christmas dresses, or ugly any-day-of-the-week dresses for that matter.

Cher 1986 Oscars

When Cher wore a skimpy Bob Mackie cage dress and matching black headpiece to the 1986 Oscars, she officially crowned herself the Queen of the Ugly Dress. The look was big with vibes of sexy, crazy, and witchy. Stars since have strived to make the same type of bold statement at red carpet events as beautiful formal dresses just don’t make the news.

Whoopi Goldberg 1993 Oscars

The 90s were a slightly boring time for red carpet looks. Most of the A-list actresses were wearing monochromatic long dresses with spaghetti straps a la Gwyneth Paltrow and Jennifer Aniston. To find our ugly dresses from this period we need to look at the musicians and the comedians. Whoopi Goldberg wore a frighteningly ugly gown when she hosted the 1993 Oscars. The garish purple and lime green disaster were so ugly it still gets more attention than anything Whoopi says on The View.

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Britney Spears 2001 AMAs

Prom dresses can be delightfully tacky, but nothing will ever outdo the epic tackiness of Britney Spears’ dress at the 2001 American Music Awards. The Southern pop star wore a full-length denim gown with patchwork and a raw hem. To top off the look, Britney brought a heap of diamonds and Justin Timberlake in a Canadian tuxedo.

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Bjork 2001 Oscars

2001 was a solid year for the ugly dress. That year, Icelandic crooner Bjork wore a dead swan draped around her neck at the Oscars. With five feet of white tulle and a flesh-colored leotard underneath, the bizarre dress looked like a figure skating outfit from a nightmare. To top off the horror show, Bjork pretended to lay an egg in the form of an egg-shaped purse.

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Soft Satin Long Sleeve Formal Dress 

Lady Gaga 2010 MTV VMAs

This list wouldn’t be complete without paying homage to the queen of on-purpose ugly, Lady Gaga. When Lady Gaga showed up to the MTV Video Music Awards in 2010 wearing leftovers from the butcher, she managed to out-ugly everyone who had come before her. The infamous “meat dress” wasn’t just ugly, it was also grouse. Made from actual raw animal flesh, the dress with matching hat, shoes, and purse was so vile that it actually stank before a taxidermist was hired to preserve it.

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Lizzo 2019 MTV VMAs

Though she’s relatively new on the red carpet scene, Lizzo already has so many memorable ugly dresses that I don’t know which one to choose. The “Truth Hurts” singer loves a feather boa and a gold lamé, and she doesn’t let her size stop her from wearing dangerously short dresses. Some of Lizzo’s best ugly plus size dresses feature literal statements written on the fabric like her red “siren” dress from the 2019 MTV Video Music Awards.

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