Every autumn, the internet remembers Rory Gilmore. The bookish, coffee-fuelled heroine of Gilmore Girls (2000–2007) has become the patron saint of fall dressing: chunky knits, plaid skirts, leather jackets and a book under the arm. Long before “dark academia” had a name, Rory was wearing it to Chilton and Yale. Here are 21 of her best looks.
What made Rory’s style work
Rory never dressed to impress, and that’s the appeal. Her clothes look like things a real student would own and wear on repeat: sweaters in autumn colours, simple skirts with tights, jeans and trainers, and one good jacket. As she grows up, from Stars Hollow High to Chilton to Yale, the pieces get a little more polished, but she still looks like Rory. For the big moments, like dances and debutante balls, she switches to romantic, old-fashioned dresses.
Her signatures:
- Knits in burgundy, rust, forest green and blue
- Plaid and A-line skirts with tights
- Leather jackets and long wool coats
- Turtlenecks and layered tees
- A messenger bag full of books
- A coffee in hand, always
The 21 best Rory Gilmore outfits
1. The Chilton uniform
Navy blazer, crest, plaid skirt: the uniform that started the whole preppy-Rory aesthetic.
Image: Pinterest · Gilmore Girls, Warner Bros. Television
2. The red zip-up sweater
Image: Pinterest · Gilmore Girls, Warner Bros. Television
3. A striped tank over a grey tee
Image: Pinterest · Gilmore Girls, Warner Bros. Television
4. Grey sweater, brown skirt
Image: Pinterest · Gilmore Girls, Warner Bros. Television
5. Long coat and a fringed scarf
Image: Pinterest · Gilmore Girls, Warner Bros. Television
6. Brown jacket over a patterned knit
Image: Pinterest · Gilmore Girls, Warner Bros. Television
7. Tan leather jacket at the mall
Image: Pinterest · Gilmore Girls, Warner Bros. Television
8. Rust sweater and cargo trousers
Image: Pinterest · Gilmore Girls, Warner Bros. Television
9. Burgundy turtleneck and boots
Possibly the most Rory outfit of all: a burgundy turtleneck, a short skirt and brown boots.
Image: Pinterest · Gilmore Girls, Warner Bros. Television
10. A green sweater for a picnic
Image: Pinterest · Gilmore Girls, Warner Bros. Television
11. Blue turtleneck for Friday-night dinner
Image: Pinterest · Gilmore Girls, Warner Bros. Television
12. Leather jacket and a plaid skirt
Image: Pinterest · Gilmore Girls, Warner Bros. Television
13. Autumn in Stars Hollow
Image: Pinterest · Gilmore Girls, Warner Bros. Television
14. The argyle sweater vest
Image: Pinterest · Gilmore Girls, Warner Bros. Television
15. Red cardigan and a headband
Image: Pinterest · Gilmore Girls, Warner Bros. Television
16. Blue tee and the messenger bag
Image: Pinterest · Gilmore Girls, Warner Bros. Television
17. Cardigan and a floral slip skirt
Image: Pinterest · Gilmore Girls, Warner Bros. Television
18. The blue dance dress
Image: Pinterest · Gilmore Girls, Warner Bros. Television
19. The debutante gown
White gown, long gloves and a nervous date: Rory’s coming-out ball, as only Emily Gilmore could arrange it.
Image: Pinterest · Gilmore Girls, Warner Bros. Television
20. A peach fifties dress
Image: Pinterest · Gilmore Girls, Warner Bros. Television
21. The lavender gown
Image: Pinterest · Gilmore Girls, Warner Bros. Television
How to dress like Rory today
Start with a stack of knits in autumn colours and a pleated or plaid skirt, and add opaque tights and brown boots. Layer a leather jacket or a long wool coat over everything, and carry a big bag that fits a book. Keep it simple and a little bit preppy. Rory’s look is about being comfortable and clever, not trendy, which is why it still feels current twenty-five years later.
Frequently asked questions
What is Rory Gilmore’s style called?
Most people call it preppy or “dark academia”: knits, plaid skirts, blazers and leather jackets in warm autumn colours.
Which schools did Rory go to?
Stars Hollow High, then the private Chilton Academy, then Yale.
Who plays Rory Gilmore?
Alexis Bledel, in the original series (2000–2007) and in Gilmore Girls: A Year in the Life (2016).
Images are embedded from Pinterest and remain the property of their owners. Gilmore Girls © Warner Bros. Television.
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