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15 Gilmore Girls Outfits That Were Too Hideous to Forget

Updated September 26, 2019 5.5k votes 792 voters 68.4k 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.

  • 1

    The Mismatched Knitwear Explosion

    Photo: Warner Bros.

    Who Wore It: Sookie St. James

    Fashion Faux Pas: Where to start with this one? The layers? The colors? The different knits? The giant bird on her chest? Sookie’s wardrobe typically reflects her bubbly personality, but in this instance, it looks like she’s taking her cues from The Lorelai Handbook of Too Many Patterns.

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  • 2

    A Rhinestone Sweater and a Cheetah Cowboy Hat

    Photo: Warner Bros.

    Who Wore It: Lorelai Gilmore

    Fashion Faux Pas: Only Lorelai would take the two most garish finds from a clothing charity drive and pair them together. Fortunately the cheetah cowboy hat and tie-dye rhinestone jacket combo comes to an end when Lorelai finds out the jacket belonged to Luke's ex. She returns it and it’s never seen again.

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  • 3

    The First Day at Chilton Outfit

    Photo: Warner Bros.

    Who Wore It: Lorelai Gilmore

    Fashion Faux Pas: Running late for Rory’s first day at Chilton, Lorelai throws on the only clean clothes she can find: a bright pink tie-dye shirt, a pair of Daisy Dukes, and cowboy boots. She tries to hide the outfit beneath a long winter coat, but once she’s in the Headmaster’s office, he asks for her coat, and Lorelai begrudgingly takes it off, much to her daughter's and mother’s embarrassment.

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  • 4

    The Bucket Hat and Oversized Necklace Duo

    Photo: Warner Bros.

    Who Wore It: Lorelai Gilmore

    Fashion Faux Pas: A classic case of over-accessorizing. Pairing a white bucket hat with an oversized flower necklace AND a top with a print and lace trimming? You've overdone it, Lorelai. On its own, the top is cute, but the accessories totally bring down this entire look.

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