20 Years Ago, Lorelai Gilmore Wore Her Most Chaotic Outfit

Lorelai Gilmore isn’t a regular mom, she’s a cool mom. Yes, her “best friends first” relationship with her daughter is a factor, but her of-the-moment style is mostly to credit for Lorelai’s persona.

Band tees with leather jackets? Slip dresses with shrugs? An entire wardrobe of funky bandanas? Lorelai’s got her style down pat. But in a Season 3 episode of Gilmore Girls, Lorelai deserted her cool mom aesthetic for a look that was much more... Emily.

Released in 2003, Episode 19, titled “Keg! Max!”, was a turbulent cocktail of disappointments. Lorelai had bumped into her ex-fiancé Max Medina at a Chilton Booster Club meeting where he was polite and nonchalant toward Lorelai, despite sharing a kiss a few episodes prior. Naturally, this unmoored Lorelai. She did what anyone would do and ranted to her best friend about it.

While Lorelai (Lauren Graham) and Sookie (Melissa McCarthy) walked around Stars Hollow, Lorelai obsessively decoded why Max didn’t give her special treatment. She complained about how his eye contact “was very lacking in meaning.”

But even the absurdity of the tirade (because, girl, you don’t like Max, remember?!) couldn’t distract me from the most ridiculous thing going on in this scene: Lorelai’s outfit.

Where do I even begin? Lorelai wore a floral print button-down with several buttons undone. Which makes sense, as she is an inn manager. But she topped it with a powder pink zip-up hoodie — and that is where my (many) questions start.

Is this a loose interpretation of “business casual”? Was it another laundry day, like in the pilot episode? Unclear. Regardless, this is a far cry from her usually put-together work looks or even her whimsical, Y2K-era ‘fits.

And then there’s a matter of the hat. Lorelai really looked into her closet that day and chose chaos. Unless she was on her way to Richard’s pretentious golf club, that gray flat cap had no business being in this scene or with that outfit.

The scene was short, by Gilmore Girls standards, and ended with Sookie and Lorelai falling in line for the famed Fiesta Burgers. And once they got there, fans were treated to a full view of Lorelai’s ensemble, i.e., her dark brown corduroy pants.

This outfit was just as chaotic as her relationship POV. Because, not only was she not interested in Max, she was also still dating coffee shop owner Alex (Billy Burke)(Bella Swan’s dad in Twilight) at the time.

Thankfully, she changed out of this silly look after lunch and all was right within the Gilmore Girls canon.