How to Copy Rory Gilmore’s Fall Style for All Your Dark Academia Dreams


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Are you an “It’s fall as soon as September 1 hits” person, or are you more of an “It’s fall as soon as the temperatures hit 65 degrees” person? We personally declare fall has begun as soon as we’re sick of summer and decide to pull out our favorite Rory Gilmore-esque sweater. Because let’s face it, nobody does fall fashion quite like the Gilmore girls.

Rory Gilmore is known for her preppy, cozy, dark academia looks (think: chunky sweaters, plaid skirts, tights, turtlenecks and simple jackets). If you aren’t in the know, dark academia went viral as a trend on TikTok in 2021 and is basically a preppy, fall style aesthetic with dark colors with Ivy League undertones. Former PureWow senior editor Dominique Hobdy wrote in her breakdown of the trend, “It’s an aesthetic that romanticizes academia, books and education with a focus on the classic European style of the literary greats. It’s what you would’ve worn to write a 20th century novel or the library carrel you’ve would have toiled away in at Harvard, circa 1919.” Rory Gilmore’s book infatuation, mixed with her naturally preppy style and obsession with the Ivy League make her a total posterchild for the trend. For the most part, dark academia consists of timeless pieces like blazers and turtlenecks in deeper hues, plaid prints and other preppy staples. For example, you cannot go wrong with loafers right now, which tie in perfectly with this aesthetic. Other fictional characters that may help you better visualize the look include Spencer Hastings from Pretty Little Liars, early seasons Blair Waldorf from Gossip Girl, Paige Matthews from Charmed and Kathryn Merteuil from Cruel Intentions. (By the way, if you’re ready to rewatch Gilmore Girls just in time for cozy season, you can stream it on Apple TV+ or Netflix.)

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After watching Gilmore Girls again (and again, and again) we’ve gotten a good grasp on what items Ms. Gilmore would gravitate toward, and pulled items from some of our favorite brands that embody this aesthetic beautifully. Here, a list of 13 items to achieve the Rory Gilmore fall fashion aesthetic.

  • Size Range: XS to XL

Rory’s oversize sweater is a piece that belongs in any fall wardrobe. This one has a cute cable-knit design on the front and sleeves and it comes in four colors (though we can see Rory most in the ivory and black versions). It’s a super versatile—and cozy—piece that can be dressed up when half-tucked into a silk slip skirt or down with your favorite jeans.

  • Size Range: XXS to XL

A mini skirt is a Rory Gilmore staple to wear with all of the sweaters, tights and jackets you can imagine. This cutie from Maeve has a button-front closure and belt loops in case you need a little more security. It has a form-fitting silhouette and pockets, too. We like that the skirt isn’t so short that you’ll feel like it’s riding up too high when you wear it, but is mini enough to show off your legs.

  • Size Range: XS to XL

A cashmere-wool blend sweater is the warm pullover of our dreams. It’s on the oversize end of the fit spectrum, which means you can add a turtleneck or second long sleeve underneath for an extra bit of warmth. The back is tapered to be a little longer, with side slits so the front can be easily tucked into your jeans or skirt.

  • Size Range: XXS to XXL

Rory Gilmore’s iconic red turtlenecks are a staple in her wardrobe, so we recommend adding one to yours. This one has a high, foldable neck and is made of a wool blend for warmth. The brand mentions the material is super comfortable and is very lightweight. This base layer is wonderful to add under just about anything or be worn alone, making it a versatile piece you’ll wear over and over again.

  • Size Range: 5 to 11

You can’t create a preppy, dark academia wardrobe without a set of loafers. Selena Gomez was recently spotted wearing a pair by this brand, which is known for its affordable yet sleek styles. They have a patent leather finish and come in three colors, too. New loafers typically require a little breaking in, so we recommend throwing on some high or mid-calf wool socks and scrunching them down over your tights to make sure your first few outings don’t result in too many blisters.

  • Size Range: 23 to 33

We know, we know, jeans trends are always changing, but we can’t help but feel like a pair of skinny flare jeans would totally complete a Rory Gilmore-esque look. This style is seriously cute, and would pair wonderfully with sneakers or boots (or the loafers above). They do have a high-rise waist and the wash pairs nicely with just about everything.

  • Size Range: 000 to 24, classic and tall

Rory isn’t a huge oversize blazer girl, and when we’re looking to emulate a preppy vibe, we aren’t either. This style is contoured to your shape and would look adorable with a mini skirt and set of tights (Rory would be proud). It’s made of a wool-spandex blend and the cuff buttons are functional. The brand suggest dry cleaning this jacket to help maintain its structure and quality over time.

8. Abercrombie & Fitch Denim Sherpa

Abercrombie & Fitch

  • Size Range: XXS to XL

Rory sports a denim jacket quite a bit in the show, and who are we to refuse one of our own? It’s meant to hit right at the top of your hips, and one reviewer mentions to size down if you want something more fitted. While we know that’s what Rory would do, you might also want to stick to your regular size if you plan on wearing this jacket with thicker sweaters. Also note that the brand mentions you should wash before you wear it to avoid any color transfer on lighter clothing.

  • Size Range: 5 to 11.5

Chuck Taylors should be a staple in every wardrobe, and the platform version offers a modern twist. Wear these when you want to dress your outfit down or just want something a little comfier on your feet. The insoles of these shoes are pretty flat, so if you have a high instep, they may not feel as comfortable for you. The classic look of these sneakers, though, make for a timeless, effortlessly cool vibe.

  • Size Range: XXS to 3XL

Going for a preppy style means always having a crisp button-down shirt on hand. Add this one, which is made of 100 percent cotton and comes in multiple colors and patterns, under a jacket or sweater vest. You may not be trying to copy Rory’s Chilton uniform, per se, but having a button-down like this would certainly help inspire a cute prep-school fit.

  • Size Range: XS to XL

Jackets are a must-have when fall rolls around and this tan one complements the changing colors of the leaves and your neutral fits. It’s 100 percent leather and has a more fitted silhouette, which aligns with Miss Gilmore’s style. There are two front pockets and it has a zip closure.

  • Size Range: A to E

Tights are a staple for fall, especially Gilmore Girls fall. If you’re emulating sweet (early seasons) Rory, you’re probably opting for a cute mini skirt with tights if you aren’t wearing pants. This pair from Spanx has a tummy support panel around the waist to sculpt your shape and the legs are slightly sheer.

  • Size Range: XS to 4XL

Rory Gilmore’s more laidback ‘fits consist of standard tees with go-to jeans (usually low rise and a bit flared because, hello, 2000s). A long-sleeve striped tee is preppy and cozy enough to be layered under a cardigan on a chilly day and paired with your favorite sneakers. This top is super affordable and the scoop neck style is flattering on almost everyone. The jersey material is very stretchy and soft, too.

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Olivia Dubyak

Commerce Editor

Olivia Dubyak is PureWow's Commerce Editor and textbook Capricorn. She studied journalism at Duquesne University in Pittsburgh, Pennsylvania, but has gone from New York City to...
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