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How to Copy Rory Gilmore’s Fall Style for the Wardrobe of Your Dark Academia Dreams

I'm dressing for Stars Hollow

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CBS photo archive/Getty Images/Dasha Burobina for PureWow

Are you an “It’s fall as soon as September first arrives” person, or are you more of an “It’s fall as soon as the temperatures hit 65 degrees” person? Personally, I declare autumn's arrival as soon as I'm sick of summer and decide to pull out my 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 classic 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 [to] 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 poster child for the trend. For the most part, dark academia consists of timeless pieces like jackets and turtlenecks in deeper hues, plaid prints and other preppy staples. For example, you can't 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. So cue up the show of your choice (though I obviously recommend Gilmore Girls) and get to shopping this list of 16 items to achieve the Rory Gilmore fall fashion aesthetic in 2024.

How I Chose the Best Rory Gilmore-Inspired Fashion Picks

After watching Gilmore Girls again (and again, and again) I've gotten a good grasp on what items Miss Gilmore would gravitate toward, and pulled items from some of my favorite brands that embody this aesthetic beautifully, while keeping materials, customer reviews and, of course, style in mind.

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Rory’s cable-knit sweater from the pilot episode is one of fans' most coveted pieces—just scroll through #rorygilmoresweater on TikTok. Lucky for you, I found this affordable dupe with the same chunky look from Quince. This one has a slightly cropped length that will go perfectly with your favorite high-waisted jeans, and it comes in six color options (though I'm partial to this pumpkin orange that I could totally see Rory wearing around Stars Hollow). It’s a super versatile—and cozy—piece that you're sure to get plenty of use out of this season.

A sleek 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, along with roomy front and back patch pockets. The brand's "magic fabric," a blend of viscose, linen, cotton and elastane, gives the skirt a form-fitting silhouette that purportedly "sculpts as it stretches," so a flattering fit is practically guaranteed. It also 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.

During any weekend binge of the show, you're sure to spot Rory wearing a cardigan or two, and this linen-blend one from Free People has that casual, academic look that perfectly encapsulates her style. Though it's on the shorter side, it's meant to have a relaxed, slouchy fit, which means you can add a turtleneck or long-sleeve top underneath for an extra bit of warmth. More than one shopper has said that it exceeded their expectations in terms of quality, so I'm shopping it ASAP.

Rory Gilmore’s iconic turtlenecks are a must in any fall wardrobe, and I recommend adding this oh-so-sophisticated one to yours. The micro-rib Everlane piece features a foldable neck and is made of a soft Supima cotton that will feel breathable if you want to layer it. No doubt thanks to its classic style and comfy fit, the style has earned tons of 5-star reviews from buyers. One says, "Fits well, is comfortable and importantly the turtleneck remains in place. A good under layer that can also be worn as an outer layer. Excellent garment." So yeah, this is a top worth buying in *multiples.*

You can’t create a preppy, dark academia wardrobe without a set of loafers, and this pair, with its textured, corduroy-like look, certainly fits the bill. They'll look so cute with a pair of slouchy socks to keep your feet extra warm—plus, reviewers rave over how just how comfy they are.

I know, I know, jeans trends are always changing, but I can’t help but feel like this slightly flared kick-crop pair would complete a Rory Gilmore-esque look in any decade. This style is seriously timeless, plus it has a stamp of approval from plenty of Madewell shoppers. One shares, "These [jeans] are the ones I reach for the most in my closet. They fit like a glove and provide an updated look [that's] easy to wear with ankle boots, sneakers, loafers or sandals. Will order several." I feel totally confident that Rory would love them for casual days on campus and beyond—and so will you.

Even if you aren't attending the annual Harvard vs. Yale game, you'll want this varsity sweater on hand to nail the Ivy League vibes. It has an oversized fit for ultimate comfort, and is conveniently machine-washable, so you can easily wear it on repeat from your favorite cafe to the library and back again. Just note that if you prefer a more classic, fitted look, the brand recommends sizing down. (Judging from Rory's closet, you could go either way and still look studiously chic.)

When the brisk fall weather hits, you'll be glad to have this cozy blanket scarf to wrap up in. I, for one, can easily picture Rory tossing this on to make it through the cold New England winters. It comes in three neutral patterns, and since it costs less than $20, you can totally pick up more than one to match with all of your coats and jackets.

Rory sports a denim jacket quite a bit in the show, and I think we can all agree that it's the ideal autumn layer. This pick from Sézane is made from GOTS-certified organic cotton, and the gold buttons give it an elevated look that, dare I say, even Emily Gilmore herself would approve of. And if denim's not your thing when it comes to jackets, it's also available in versatile black and camel shades, plus a trendy leopard print.

PureWow Senior Commerce Editor Stephanie Maida points to this wool-blend plaid skirt as another Rory-approved pick. She says, "I snagged this Amazon skirt last fall and it quickly became one of my most-worn items of the season. The quality is so impressive for the price, and the high-waisted fit is incredibly flattering. I definitely feel like I'm channeling Rory when I pair it with a fitted turtleneck and tights." It's a totally budget-friendly find, too, and comes in a ton of different color combos to choose from.

Going for an academic look means always having a crisp button-down shirt on hand. I suggest snagging this one, which is made of 100 percent cotton that's been washed to have an already lived-in feel. It comes in multiple colors and patterns, and easily layers under a jacket or sweater vest. You may not be trying to copy Rory’s Chilton uniform, per se, but having a classic top like this would certainly help inspire a more mature prep-inspired fit.

Cute, versatile and functional jackets are a must-have when autumn rolls around and this cognac one is sure to complement the changing colors of the leaves and all your neutral fits. It’s 100 percent leather and has a fitted silhouette with a stand collar, which definitely aligns with Miss Gilmore’s 2000s style. As for its functionality, it's equipped with two front pockets and has a zip closure that you'll appreciate as it gets colder.

Tights are an essential, especially when you're channeling a 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 jeans. This pair from Spanx has a tummy support panel around the waist, along with medium compression for added sculpting. And while the legs are slightly sheer, they should definitely supply enough coverage on chilly days.

Rory's more laid-back fits consist of standard tees and jeans (usually low rise and a bit flared because, hello, 2000s). And this tuckable ribbed tee feels like just the thing she'd toss on under a cardigan for a day of coffee at Luke's followed by some browsing at Stars Hollow Books. Its featherweight fabric is made from a modal blend that shoppers confirm feels just as comfortable as PJs. One reviewer writes, "The featherweight line is unmatched. I feel like I am wearing pajamas to work but look pulled together. I never have to iron this top and [it] tucks seamlessly into my pants. It’s a staple item." Yep, this is going straight in my cart for Gilmore season.

Whether it's a Friday night dinner with her grandparents or Yale alumni party, Rory always has a go-to dress on hand for fancier occasions, and this on-trend drop-waist style feels like something she'd pull out of her closet. Its bodice is made of modal, while the skirt is cotton, so it'll feel super breathable on your skin as you socialize. Plus, you can easily change up its look with different jackets, jewelry and shoes. What else would you expect from a good LBD?

It wouldn't be a Rory Gilmore-inspired outfit without a spacious bag that could fit books, journals, pens and more alongside the usual essentials, and this roomy bucket bag is just that. It has a magnetic closure at the top to keep everything secure, and the inner pouch is removable, so you can use it separately, too. Shoppers say it feels super lightweight but sturdy, and one even calls it the *perfect* carryall: "This might just be the perfect bag. Not too big or small, lightweight but sturdy, soft as butter. I purchased the green, but now I want them all!" Well, I'm sold, especially on this very dark academia-coded chocolate hue. 


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Assistant Commerce Editor

  • Writes commerce stories and features that span multiple topics, including fashion, beauty, travel, home and sales/deals
  • Has contributed to reports on ethical fashion and continues to stay up-to-date on sustainablility developments
  • Completed a bachelor's degree in psychology at the University of Pittsburgh and a master's degree in fashion studies at Parsons The New School

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Commerce Editor

  • Covers commerce content, including personal and collaborative reviews and product roundups across beauty, home, fashion and family verticals
  • More than 5 years of professional experience in journalism
  • Studied journalism at Duquesne University

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