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15 Gilmore Girls Outfits That Were Too Hideous to Forget

Updated September 26, 2019 5.5k votes 790 voters 68.3k views15 items

List RulesVote up the hideous Gilmore Girl outfits you can never unsee.

Although Stars Hollow is a tiny town, it has a lot of style - unique style, that is. Over the course of seven seasons, fans were graced with some heinously bad Gilmore Girls outfits. The majority of those outfits belong to everyone’s favorite wacky-print-wearing, sparkle-loving mom and part-time dressmaker, Lorelai Gilmore. Given some of her more outrageous fashion choices, it’s hard to believe she could make something as lovely as Rory’s prom dress.

While Lorelai is charged with some of the most major Gilmore Girls fashion faux pas, the rest of the Stars Hollow gang isn’t without guilt. Who could forget the atrocious velvet dress Emily made Rory don for her portrait? Or Lane’s pre-Lorelai’d wedding dress? Or Jackson’s pajamas? Never forget Jackson’s pajamas.

As atrocious as some of these outfits are, they drive home the quirkiness we all love about Stars Hollow, with all its cooky residents. Celebrate their uniqueness by voting up the ugliest outfits on Gilmore Girls and promise to never wear a cheetah print cowboy hat ever in your life.

  • 5

    Wrestling Pajamas

    Photo: Warner Bros.

    Who Wore It: Jackson Douglas

    Fashion Faux Pas: Everyone wears pajamas that feature pictures of themselves in their high school wrestling uniform, right? Jackson sure does! While the pajamas are ridiculous, and Jackson hopes to hide them from Lorelai and Rory, there is a certain charm to them. If you need to see what a real man looks like, look no further than Jackson Douglas when he’s donning these PJs, which he sweetly wears because his cousin made them for him.

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  • 6

    The Sort of Matching Beanie and Scarf

    Photo: Warner Bros.

    Who Wore It: Lorelai Gilmore

    Fashion Faux Pas: This patchwork beanie and striped scarf would be cute if they were each worn separately, but Lorelai doesn’t do anything small. The bigger the better, the louder the better, the brighter, pinker, more colorful, more mismatched, the better.

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  • 7

    The Coming Out Dress

    Photo: Warner Bros.

    Who Wore It: Lorelai Gilmore

    Fashion Faux Pas: When Rory formally came out to society, she looked beautiful. Her dress was simple and elegant. When Lorelai came out, she wore a tulle nightmare come to life. The dress perfectly encapsulates the differences between young Lorelai and her mother. Emily, of course, wanted something very formal and respectable for her only daughter, which, as this list can attest, is a far cry from the free-spirited Lorelai.

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  • 8

    The Fashion Show Outfits

    Photo: Warner Bros.

    Who Wore It: Lorelai and Emily Gilmore

    Fashion Faux Pas: While fans were undoubtedly overjoyed to see their second favorite mother-daughter combo getting along for a brief time, the outfits they wore almost stole the scene - and not in a good way. Keep in mind that these clothes were meant to be sold for a charity auction. Emily and Lorelai do a great job of showing them off, but surely the Booster Club could have picked something more befitting these lovely ladies.

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