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Home Fall Gilmore Girl Outfits: Reimagining Rory & Lorelai’s Style for Fall 2024
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Gilmore Girl Outfits: Reimagining Rory & Lorelai’s Style for Fall 2024

  • Jafei Pollitt
  • August 11, 2024
  • Contains Affiliate Links

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.

Photo Credit: Netflix & Warner Bros.

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. 

 
Hoerev High Waist Pleated Skirt
 
Hollister Cable-Knit Crew Sweater Vest
 
Mary Jane Loafers
 
Karsyn Lettuce Edge Crew Socks
Hoerev High Waist Pleated Skirt
Hollister Cable-Knit Crew Sweater Vest
Mary Jane Loafers
Karsyn Lettuce Edge Crew Socks
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Hoerev High Waist Pleated Skirt
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Mary Jane Loafers
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Karsyn Lettuce Edge Crew Socks
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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. 

 
Levi's Racer Faux Leather Jacket
 
Hoerev High Waist Pleated Skirt
 
Anthropologie Jeffrey Campbell Hot Lava Boots
 
Hanes Women's Curves Sheer Black Tights HSP006
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Hanes Women's Curves Sheer Black Tights HSP006
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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.

 
Black Mini Skirt
 
Leather Shoulder Bag
 
Anthropologie Jeffrey Campbell Hot Lava Boots
 
Hollister Cable-Knit Crew Sweater Vest
Black Mini Skirt
Leather Shoulder Bag
Anthropologie Jeffrey Campbell Hot Lava Boots
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Black Mini Skirt
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Leather Shoulder Bag
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Anthropologie Jeffrey Campbell Hot Lava Boots
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Hollister Cable-Knit Crew Sweater Vest
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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!

 
ZESICA Turtleneck Chunky Knit
 
Madewell Curvy Perfect Vintage Short in Dewberry Wash
 
Dr. Martens 1460 Lace Up Boots
ZESICA Turtleneck Chunky Knit
Madewell Curvy Perfect Vintage Short in Dewberry Wash
Dr. Martens 1460 Lace Up Boots
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ZESICA Turtleneck Chunky Knit
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Madewell Curvy Perfect Vintage Short in Dewberry Wash
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Dr. Martens 1460 Lace Up Boots
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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!

 
Soft Chiffon Shawl Wrap
 
Gap Modern Rib Cardigan
 
Shimma White Satin Mini Dress
 
Chinese Laundry YANDA Pump
 
White Corset With Embroidered Flowers
Soft Chiffon Shawl Wrap
Gap Modern Rib Cardigan
Shimma White Satin Mini Dress
Chinese Laundry YANDA Pump
White Corset With Embroidered Flowers
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Soft Chiffon Shawl Wrap
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Gap Modern Rib Cardigan
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Shimma White Satin Mini Dress
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Chinese Laundry YANDA Pump
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White Corset With Embroidered Flowers
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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!

 
MANGOPOP Black Long Sleeve Square Neck Bodysuit
 
SweatyRocks Ribbed-Knit Crop Vest
 
Hollister Ultra High-Rise Baggy Jeans
 
Converse Chuck Taylor All Star High Top Sneaker
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SweatyRocks Ribbed-Knit Crop Vest
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05/27/2025 11:24 am GMT

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. 

 
Old Navy Classic Button-Down Shirt
 
Pullover Sweater
 
The Way-High Jean
 
adidas Originals Samba OG
 
BAGGU Nylon Messenger Bag
Old Navy Classic Button-Down Shirt
Pullover Sweater
The Way-High Jean
adidas Originals Samba OG
BAGGU Nylon Messenger Bag
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Old Navy Classic Button-Down Shirt
Old Navy Classic Button-Down Shirt
Buy Now
Pullover Sweater
Pullover Sweater
Shop Now
The Way-High Jean
The Way-High Jean
Buy Now
adidas Originals Samba OG
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BAGGU Nylon Messenger Bag
BAGGU Nylon Messenger Bag
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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. 

 
Kiel James Patrick Sweaters
 
The Jean Jacket in Medford Wash
 
Chunky Brown Loafer
 
Quince Stretch Corduroy Flare Pants
 
Black Mini Skirt
 
Callie Faux Leather Jacket Burgundy
 
Journee Collection Veralee Bootie
Kiel James Patrick Sweaters
The Jean Jacket in Medford Wash
Chunky Brown Loafer
Quince Stretch Corduroy Flare Pants
Black Mini Skirt
Callie Faux Leather Jacket Burgundy
Journee Collection Veralee Bootie
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Kiel James Patrick Sweaters
Kiel James Patrick Sweaters
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The Jean Jacket in Medford Wash
The Jean Jacket in Medford Wash
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Chunky Brown Loafer
Chunky Brown Loafer
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Quince Stretch Corduroy Flare Pants
Quince Stretch Corduroy Flare Pants
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Black Mini Skirt
Black Mini Skirt
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Callie Faux Leather Jacket Burgundy
Callie Faux Leather Jacket Burgundy
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Journee Collection Veralee Bootie
Journee Collection Veralee Bootie
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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.

 
Madewell Carabiner Medium Hoop Earrings
 
Berydress Classic 3/4 Sleeve V Neck
 
Gold Block High Heels
Madewell Carabiner Medium Hoop Earrings
Berydress Classic 3/4 Sleeve V Neck
Gold Block High Heels
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Madewell Carabiner Medium Hoop Earrings
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Berydress Classic 3/4 Sleeve V Neck
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Gold Block High Heels
Gold Block High Heels
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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.

 
Quince 100% Leather Shirt Jacket
 
Sunfaynis Soft Cotton Mock Turtleneck Shirt
 
Madewell Harlow Wide-Leg Pant
 
Journee Collection Veralee Bootie
Quince 100% Leather Shirt Jacket
Sunfaynis Soft Cotton Mock Turtleneck Shirt
Madewell Harlow Wide-Leg Pant
Journee Collection Veralee Bootie
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Quince 100% Leather Shirt Jacket
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Sunfaynis Soft Cotton Mock Turtleneck Shirt
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Madewell Harlow Wide-Leg Pant
Madewell Harlow Wide-Leg Pant
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Journee Collection Veralee Bootie
Journee Collection Veralee Bootie
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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. 

 
Knit Fabric High Neck Long Sleeve Top
 
Abercrombie Black Ultra High Rise 90s Straight Jean
 
Quince 100% Leather Shirt Jacket
 
Journee Collection Veralee Bootie
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Abercrombie Black Ultra High Rise 90s Straight Jean
Quince 100% Leather Shirt Jacket
Journee Collection Veralee Bootie
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Knit Fabric High Neck Long Sleeve Top
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Abercrombie Black Ultra High Rise 90s Straight Jean
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Quince 100% Leather Shirt Jacket
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Journee Collection Veralee Bootie
Journee Collection Veralee Bootie
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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! 

 
Light Wash Boyfriend Jeans
 
Abercrombie Red Pepper Graphic Baby Tee
 
Vismaya Floral Cobalt Bandana
 
Converse Chuck Taylor All Star High Top Sneaker
Light Wash Boyfriend Jeans
Abercrombie Red Pepper Graphic Baby Tee
Vismaya Floral Cobalt Bandana
Converse Chuck Taylor All Star High Top Sneaker
Shop Now
Buy Now
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Light Wash Boyfriend Jeans
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Shop Now
Abercrombie Red Pepper Graphic Baby Tee
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Buy Now
Vismaya Floral Cobalt Bandana
Vismaya Floral Cobalt Bandana
Buy Now
Converse Chuck Taylor All Star High Top Sneaker
Converse Chuck Taylor All Star High Top Sneaker
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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. 

 
Quince Lightweight Cotton Cashmere Crew Sweater
 
Wrangler Girlfriend Sherpa Jacket
 
Sezane Martin Crop Trousers - Brown Gingham
 
Silent D Naydo Heeled Ankle Boots
Quince Lightweight Cotton Cashmere Crew Sweater
Wrangler Girlfriend Sherpa Jacket
Sezane Martin Crop Trousers - Brown Gingham
Silent D Naydo Heeled Ankle Boots
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Quince Lightweight Cotton Cashmere Crew Sweater
Quince Lightweight Cotton Cashmere Crew Sweater
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Wrangler Girlfriend Sherpa Jacket
Wrangler Girlfriend Sherpa Jacket
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Sezane Martin Crop Trousers - Brown Gingham
Sezane Martin Crop Trousers - Brown Gingham
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Silent D Naydo Heeled Ankle Boots
Silent D Naydo Heeled Ankle Boots
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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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Hoerev High Waist Pleated Skirt
Hoerev High Waist Pleated Skirt
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Hollister Cable-Knit Crew Sweater Vest
Hollister Cable-Knit Crew Sweater Vest
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Mary Jane Loafers
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Karsyn Lettuce Edge Crew Socks
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Steve Madden Lucine Black Leather Mary Jane Platforms
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ZESICA Turtleneck Chunky Knit
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Madewell Curvy Perfect Vintage Short in Dewberry Wash
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Dr. Martens 1460 Lace Up Boots
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Soft Chiffon Shawl Wrap
Soft Chiffon Shawl Wrap
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Gap Modern Rib Cardigan
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Shimma White Satin Mini Dress
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Chinese Laundry YANDA Pump
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White Corset With Embroidered Flowers
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MANGOPOP Black Long Sleeve Square Neck Bodysuit
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SweatyRocks Ribbed-Knit Crop Vest
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Hollister Ultra High-Rise Baggy Jeans
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Converse Chuck Taylor All Star High Top Sneaker
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Madewell Carabiner Medium Hoop Earrings
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Berydress Classic 3/4 Sleeve V Neck
Berydress Classic 3/4 Sleeve V Neck
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Gold Block High Heels
Gold Block High Heels
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Quince 100% Leather Shirt Jacket
Quince 100% Leather Shirt Jacket
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Sunfaynis Soft Cotton Mock Turtleneck Shirt
Sunfaynis Soft Cotton Mock Turtleneck Shirt
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Madewell Harlow Wide-Leg Pant
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Journee Collection Veralee Bootie
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Levi's Racer Faux Leather Jacket
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Hanes Women's Curves Sheer Black Tights HSP006
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Anthropologie Jeffrey Campbell Hot Lava Boots
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Black Mini Skirt
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Leather Shoulder Bag
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Old Navy Classic Button-Down Shirt
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Pullover Sweater
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BAGGU Nylon Messenger Bag
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Quince Stretch Corduroy Flare Pants
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Callie Faux Leather Jacket Burgundy
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Knit Fabric High Neck Long Sleeve Top
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Abercrombie Black Ultra High Rise 90s Straight Jean
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Light Wash Boyfriend Jeans
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Abercrombie Red Pepper Graphic Baby Tee
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Vismaya Floral Cobalt Bandana
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Quince Lightweight Cotton Cashmere Crew Sweater
Quince Lightweight Cotton Cashmere Crew Sweater
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Wrangler Girlfriend Sherpa Jacket
Wrangler Girlfriend Sherpa Jacket
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Sezane Martin Crop Trousers - Brown Gingham
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Silent D Naydo Heeled Ankle Boots
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Jafei Pollitt

I’m an avid pathos plant grower, hamster enthusiast, and a sucker for a good spell! When I’m not writing, you can find me outside attempting to do some yoga or trying out a new boba shop. Check me out at jafeipollitt.com!

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6 comments
  1. fnaf says:
    June 13, 2024 at 7:35 pm

    I’m so lucky to have found this site, which gave me easy access to good information

    Reply
  2. nytwordlehints says:
    July 3, 2024 at 6:48 pm

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  3. Evelina says:
    October 12, 2024 at 9:14 am

    Terrible ideas which do not bear the slightest resemblance to the original outfits.

    Reply
  4. hiked07 says:
    April 2, 2025 at 12:42 am

    Omg, I love this! Gilmore Girls fall fashion is totally timeless. These modern takes on Rory’s outfits are so cute and wearable. Need that sweater vest ASAP!

    Reply
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    April 9, 2025 at 11:06 pm

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  6. kunpeng says:
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        Whimsy Soul is a lifestyle website founded by Kara Harms. Together with a team of talented Whimsy Writers, we inspire our community to take the ordinary and make it extra.
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