Are you a Rory or a Lorelai? Or maybe you match with Sookie the best! Some might say Gilmore Girls is the ultimate fall show to binge on Netflix. It aired in 2000, aka y2K, which is making a huge fashion comeback, so it’s great inspo for new fall outfits!
We reimagined some iconic Rory Gilmore outfits for the present day so you can have that Gilmore Girls aesthetic all season long.
Gilmore Girl Outfits: Reimagining Rory Gilmore’s Style for Fall
Grab your PSL (or black and in an IV like Lorelai), and let’s take a look at Rory’s iconic style.
What is the Aesthetic of Rory Gilmore?
The thing about Y2K is it’s on the brink of the 90s and 2000s. When we’re introduced to Rory in the Gilmore Girls pilot, she’s wearing the iconic white wool fisherman sweater with jeans. Very, very 90s.
In these early episodes especially, she follows 90s fashion almost to a tee with low-rise jeans, t-shirts over long sleeves, and eclectic color combos. She’s honestly got some fantastic outfits that just need a minor tweak to fit into 2022.
Rory Gilmore’s Iconic Outfits ReImagined
After digging through her most iconic outfits, like the Rory Gilmore white sweater fit, and binge-watching all the seasons, we took to the internet to turn the Rory Gilmore style into modern outfits you can shop and wear right in time for fall! Let’s start with a favorite – Rory’s school fit.
The Chilton Private School Uniform
We’re introduced to the Chilton Uniform early on when Lorelai is hemming Rory’s skirt. While many wear unwillingly wear school uniforms, Rory’s vintage private school outfit is a look and we turned it into something you can wear on a sunny day!
The 21st century is obsessed with pleated tennis skirts, so it was a no-brainer that we needed to keep that energy going. We swapped Rory’s old-school skirt for a short beige one (as beige is all the rage).
Following the color theme, we swapped her stifling top and jacket for a cropped, knitted sweater vest that shows a little more skin. You can easily layer this piece with a long sleeve shirt or turtleneck underneath as the weather gets colder.
On her first day at Chilton, all the focus is on Lorelai’s cowboy boots, and you might miss Rory’s black and white saddle shoes. We swapped those for a chunky Mary Jane shoe in black and little lace socks that make the whole thing pop!
To be fair, this Gilmore Girls outfit isn’t very fit for school, but it’s a cute style for autumn, and so versatile – you can layer as it gets colder or mix and match with whatever else you’ve got going on in your closet.
I’s a perfect outfit for heading to a coffee shop or bookstore for some Insta pics! Caption it with one of Kara’s 70+ fall Instagram captions.
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College Rory in Pleated Skirt
If you want a slight variation of Rory’s Chilton uniform. This college look takes it up a notch with a tan leather jacket, tights and knee high boots. We see the evolution, Rory, and we’re here for it.
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Wild Card: Lorelai’s Fall “Chilton Uniform” Fit
Ditch the tights and swap the pleated skirt for black mini (also a Meg Ryan favorite) to capture Lorelai’s fall outfit. The rectangular black frames are even back in style! Style is truly cyclical.
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The Iconic Sweater Fit
The Rory Gilmore sweater outfit is one of the first outfits we see her in on one of her last days at Stars Hollow High School, and one of the first things you’ll see when you search for outfits on the show. It’s a great ensemble (and a fab chunky sweater!) that can easily make its way into 2024 with some minor adjustments.
If you’re asking yourself, “how do I dress like Rory Gilmore?” you’ll want to start with this Gilmore Girls style. Rory’s giant white cable knit sweater is the star of the outfit. We wanted to keep it, but maybe not all of it. We swapped the Rory sweater for a smaller, cable knit sweater that holds around the waist, but still gives you that nice, baggy feeling of an oversized sweater. The sweater Gilmore wore was cute, but looked insanely heavy – so we lightened the load.
Rory paired the giant sweater with long black jeans, but we’re going for denim shorts to give the whole outfit a little more oomph. It’s the perfect choice for the season of apple picking! Psst – check out Kara’s article on 12 cute outfits for apple picking this fall! While we don’t get a clear look at Rory’s shoes, we imagine a dark boot would pair well, and of course, Dr. Martens are making an appearance – the perfect leaf-stomping shoes. Everyone and their mother loves Dr. Martens and they’re perfect all year round for every season. Yes, the price is up there, but these puppies sure do last.
This knit sweater outfit is a lovely little three-piece to add to your closet and wear at home or out on fall adventures!
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The Life & Death Brigade Dress
It’s unclear if Logan Huntzberger was going for a Mary Poppins look when he chose Rory’s look for her introduction to The Life & Death Brigade festivities in Season 5, but the photo we grabbed screams spoonful of sugar!
This fit was one of our faves, so let’s get into how we modernized it. Starting with the blue scarf, we decided to switch it up with a sheer, light blue shawl. Our upgrade gives the outfit a youthful glow from the original ensemble while also brightening the whole look! For something warmer, match it with a light cardigan instead.
Rory wore a stunning dress on the show, but we wanted to add a little spice. We traded her long, formal gown for a satin mini dress. This piece gives the whole look a facelift while keeping the elegance and adding a hint of sexiness!
We finished with a light blue chunky heel to match the shawl and tie in the whole outfit. These shoes are to die for, and would also make a great gift!
If you want to spice this look up even more, swap the shawl for an underbust corset. Etsy has some incredible corsets with adorable flower embellishments that add a little sweetness! This outfit is great for a Friday night dinner date or party. In omnia paratus!
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The Casual Everyday Look
You can’t wear a fancy dress every day in Rory’s hometown, Stars Hollow, so we picked out one of her day-to-day outfits to even it out. This piece has some great colors and not-so-great body framing, so we took it and rearranged it.
Let’s dive in! It’s not 2024 if we don’t include at least one body suit. We picked out the perfect long sleeve, black body suit to start off this outfit! It has a great square framing around the neck, and sits snugly under the vest. We kept it simple by replacing her full, short sleeve sweater with a cropped knitted vest. This vest’s v-neck is a perfect twist to Rory’s original. And if you get too warm? Just pop off the vest and you still have a stellar outfit!
No more low-waist jeans. Please. Let’s leave them in the past. We subbed her low rise for wide-leg jeans that sits on the waist, giving you a great shape with a little distress at the knees for that “cool girl” aesthetic
Ending on a 90s classic, we stuck with the high top black Converse to complete this look. This shoe is timeless, casual, and works for almost anything. Looking for something else comfy and casual for fall? Check out Kara’s 14 fall fashion staples!
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A Preppy Take On Rory’s Comfy Casual
Another reimagined Rory outfit with a little bit of that preppy spice she started to add in college. (Influenced by Logan’s crowd, maybe?!) Just add a collared shirt under a sweater with a book bag (this one from Baggu is chef’s kiss!), and you too can stroll seamlessly across Yale campus.
To freshen up the look for 2024, throw on a pair of Adidas Sambas, and you’ll give “it girl” vibes.
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Rory and Lorelai’s Arm-In-Arm Look
Since both of these outfits have the same formula, it made sense to pair them together! Rory is sporting a patterned sweater with what kinda look like corduroys. Let’s bring back the corduroys, but pair it with loafers instead. Top it with a jean jacket at your leisure.
Lorelai is has a monochrome look going on with a red leather jacket (iconic) and red button down. We’re going to reimagine that with the black mini skirt, tights and some black booties.
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Lorelai Gilmore’s Outfits Reimagined (But Only Slightly!)
Let’s not forget the other women contributing to the Gilmore Girls fashion. Lorelai Gilmore is a style icon. We redesigned a few of her ensembles for the modern day that you’ll love!
Lorelai’s High School Graduation Dress
This look was featured in the episode with Rory’s teary high school graduation, and Lorelai was stunning (per usual).
We added some simple gold hoops because this outfit is fairly simple, and needed some good accessories. Great for every size and figure, we subbed Lorelai’s dress for a sexy, bodycon wrap dress in deep rouge. We wrapped up the outfit and included a pair of bold gold sandals with a little heel.
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Lorelai’s Perfect Fall Outfit
This ensemble was pretty much perfect already. We just made it easier to get the pieces yourself! An oversized leather jacket to match Lorelai’s because hers was already *chefs kiss.* We found a sleeveless turtleneck that goes perfectly with the pants and leaves some room to breathe.
The only change we made. We swapped the pencil skirt she wore for some sleek, wide-leg pants! Nothing says fall more than a black, heeled boot which is exactly what we added! A nice crocodile print bootie with a chunky heel to pull the outfit all together.
Lorelai’s fall fit is a must if you want to dress in real Gilmore Girls style. Follow it up with your hair slicked back into a low pony, and you’ll have Luke Danes knocking on your door.
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A Pop of Red
We’re predicting the pop of red trend will continue into the 2024 fall season, and Lorelai nailed it with this look. It really worked for her from business school to parents night at Chilton. She even wooed one of Rory’s teachers! To make it a bit more casual, we swapped in some black jeans.
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Lorelai Working Around The House Outfit
No matter what she’s up to, Lorelai always puts together a fun outfit. We especially love when she rocks the hair bandana as she works around the house or on set sewing costumes for the local theater. Modernize the look by swapping the baseball tee for a trendy baby tee with a pepper that we think Lorelai would get a kick out of!
Pair with a light wash jean, cute patterned hair scarf and sneakers for a complete look!
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Iconic Corduroy Jacket
Lorelai really loved this jacket. Meaning we saw it at least more than once! We decided to really mix it up for this outfit… and pay homage to Lorelai’s love to step out of the ordinary. A corduroy jacket with sherpa lining with gingham pants and booties.
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Add to Cart!
We’ve given you the lowdown on Gilmore Girls’ outfits you’ll love; now it’s time to add to cart and look like a modern day Gilmore Girl!
Let me know what other characters I should recreate fashion looks for in the comments below!
And, honestly, when in doubt you can usually always find a lot of Gilmore Girls clothing and New England college girl style at companies like Sezane, Shop Cider, Old Navy and Anthropologie.
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Terrible ideas which do not bear the slightest resemblance to the original outfits.