'Gilmore Girls': 19 Times Rory Gilmore Was Our Fall Outfit Inspiration

rory gilmore fall outfits gilmore girls
credit: Warner Bros.

Ah, the early aughts fashion of Gilmore Girls. Is there anything better?

Now that the 90s are back, it’s only a matter of time before the early aughts starts creeping into our wardrobes again. So who else would we turn to but our favorite mother-daughter duo?

Lorelai and Rory both had (ahem) unique tastes in clothes. One moment Lorelai would be wearing something super tacky and Rory something super frumpy, and the next, they’d be wearing something super cute.

But luckily for Rory, her style only got better as the show progressed. In college, she cultivated a preppy but cute wardrobe and by the end of the series, she was looking more put together than ever.

Below, we’ve gathered the Yale graduate’s best fall outfits so you can channel your inner Rory and start quoting Earnest Hemmingway at the drop of a hat. So, without further ado, and in no particular order, Rory’s cutest fall fashion — and how to recreate them.

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1. “And eat and eat and eat.”

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The perfect coat to wear to not one, not two, not three, but four Thanksgiving dinners.

2. “Like Roz Russell and Ava Gardner on Fifth Avenue”

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The perfect outfit for window shopping!

3. “It’s Avril Lavigne’s world. We’re just living in it.”

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When dealing with an angry ballerina, always opt for a cable-knit sweater.

4. “They make very good cakes here. they’re very… round.”

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When meeting your first love, go with the combat boots, my friend.

5. “I’m gonna have to quit drinking coffee! And I love coffee!”

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Looking cute in therapy is always a priority.

6. “Oh, good, you’re using ‘e’s.”

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Interviewing the members of the Life and Death Brigade requires a good coat and at least five notebooks.

7. “I’ll give you twenty bucks for the tree.”

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When you find the perfect tree, never let it go.

8. “I love you.”

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When your ex-boyfriend chases you around the town square to tell you he loves you, the least you can do is look irresistible.

9. “Well, it’s a newspaper hat. It’s not supposed to spark a trend.”

rory gilmore outfit

The hat *makes* the outfit.

10. “Yes, I have to go to the fro-yo social. And yes, I do realize how incredibly stupid that just sounded.”

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When you need to call someone a “jerk, ass, arrogant, inconsiderate, mindless, frat boy, lowlife, buttface miscreant,” go with a fair isle sweater.

11. “Yale is a magical place, Anna. A magical, magical place.”

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Greeting a high schooler from your alma mater requires a camo mini skirt, obviously.

12. “He’s the boy who dissected a frog, did not wash his hands, and then ate a sandwich.”

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Whatever you do, don’t accept the butt napkins.

13. “Well, hot-plate Harriet took it very badly.”

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This outfit screams, “my crazy best friend/roommate just kicked me out and I’m desperately trying to keep my shit together.”

14. “From now on, I would appreciate it if you would refrain from telling the hilarious laundry room incident to anyone, anywhere, ever again.”

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Being self-involved means thinking a boy you asked out in the laundromat is spreading gossip about you when he’s actually talking about someone else.

15. “What are you doing? Living at your grandparents’ place, being in the DAR, no Yale… why did you drop out of Yale?!”

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You’re going to want to look your best when your ex-boyfriend knocks some sense into you.

16. “So, do we go in, or do we just stand here reenacting The Little Match Girl?”

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This totally innocent look is perfect for a Friday night dinner with the grandparents.

17. “I didn’t bloom. My headpiece malfunctioned.”

rory gilmore style

Showing your boyfriend around your hometown requires a double-breasted denim jacket.

18. “There is so much joy around me, I’m gonna hurl.”

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If you’re going to be the last one on campus to turn in their final, you’re going to need a comfy cardigan and button-up shirt.

19. “Wow, I can hear the disappointment from here.”

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Is there anything worse than knowing your best friend’s mom hates you?


‘Gilmore Girls’: 15 Times Rory Gilmore’s Winter Outfits Were On-Point

Lena Finkel
Lena Finkel is the Editor and Founder of Femestella. Prior to starting Femestella, she worked at People, InStyle, Tiger Beat, and Sesame Workshop (aka Sesame Street). She loves all things Real Housewives and Vanderpump Rules. When she's not busy binge-watching TV, you can find her hanging out with her tuxedo cat Tom.