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Fall Fashion (2000's Version)
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items Discover the best fall fashion from the 2000s — from cozy layered looks and denim minis to iconic boots, scarves, and Y2K accessories. Relive nostalgic autumn style inspiration from the early 2000s and find outfit ideas perfect for crisp weather, cam...
Sections
8
Meg Ryan Starter Pack
Denim
Sweaters
Shoes
Mini Skirts
Outerwear
Meg Ryan Starter Pack
What you should wear if you want to look like Meg Ryan in a Nora Ephron film.
Red knit, it's a necessity
Women's Red Sweaters
A ludicrously capacious bag for books and such.
Burgundy Tote Bags for Women
The gateway bootcut—classic, easy, goes with every fall boot. Think Gilmore Girls town-square chic: Rory in Stars Hollow crunching through leaves on the way to Luke’s.
Women's Low Rise Bootcut Jeans
Skort with a cutie lil belt
LOW-RISE BELTED SKORT
AN ESSENTIAL!
UO Essential Metal Rectangle Sunglasses
iykyk
Too Smart For Her Own Good ? by Conalee Levine-Shneidman
Denim
Shawty had them apple bottom jeans, now you can too.
If your ringtone was “Since U Been Gone,” these seams are your personality. Oversized stitching, rhinestone pockets, and a little Hollywood club energy—they basically scream paparazzi flashbulbs outside Hyde.
BECCA BIG T STITCH BOOTCUT JEAN - Sun Blazed
The TRL era jean—low, long, and made to skim chunky sneakers. They feel straight out of a 2004 mall trip where you’re sipping an Orange Julius, texting on a pink Razr, and waiting for your friends at Abercrombie.
Women's Flare Jeans
That Italian Y2K attitude—slouchy, low-key, a little rebellious. They have the perfect “don’t care but actually styled this” vibe that pairs with chunky belts, layered tanks, and smudgy eyeliner.
Women's Bootcut and Flare Jeans | Light Blue | Diesel 2000 Widee
The jeans so iconic they literally have their own song. Apple Bottoms were the early-2000s holy grail—bootcut, low-rise, and designed to hug curves in all the right ways. Think metallic stitching, rhinestone back pockets, and logos so loud you could ...
Apple Bottom Jeans
The bootcut revival you didn’t know you needed. Dark wash, leg-elongating, and ready to stomp through crunchy leaves with your UGGs or heels. Think early-2000s J.Lo, but cozier.
Curvy Mid-Rise Dark Wash Boot Jeans - Bottoms
Sweaters
Cable-knit, cropped, or falling off one shoulder like it’s an episode of Gilmore Girls.
This sweater is SO giving Rory Gilmore at Chilton. Makes me want a cup of coffee real bad.
Jessy Cable Knit Oversized Sweater
Classic knit, and a fit that says “I'm going to be 7th grade class secretary” in the best way. Toss it on over a lsce cami for peak tween fashion.
Women's Cable-Knit Heart Crew Sweater
Just like the other sweater, but this time in a V NECK!
Women's Cable-Knit Icon V-Neck Sweater
Sweet, preppy, and just the right amount of flirty. The square neckline screams Delia’s catalog, and the short sleeves keep it perfect for layering with mini skirts and long necklaces.
Women's Short-Sleeve Square Neck Sweater
I actually think I need one in every color...
Women's Short-Sleeve Square Neck Sweater
A babydoll cut with cable knit texture—flowy, comfy, and begging to be paired with a denim mini and leg warmers.
Cable-Knit Babydoll Sweater - Women's Tops
Cozy meets Y2K coquette. The square neckline keeps it polished while the babydoll shape makes it twirl-worthy. Add a corduroy mini or flare jeans and you’re suddenly main-character walking through the quad.
Easy Long-Sleeve Square-Neck Babydoll Sweater
Grandma’s cardigan but make it Y2K. Sweet eyelet details, cropped just right, and perfect for wearing half-buttoned over a lace cami like you’re in a 2003 rom-com.
Women's Eyelet Crew Cardigan
All the sweater vibes, none of the pants required. Pair with tall boots for instant Gossip Girl side character realness—or UGGs if you’re going for mall rat chic.
Women's Oversized Cable-Knit Crew Sweater Dress
Shoes
UGGs, Converse, Steve Madden… the holy trinity of hallway runways.
If you didn't have these in my middle school, you were nobody. I was nobody lol.
Women's Bailey Bow II
Cozy house-to-bodega slides. They’re for days when you’re running late, hair still wet, but you want that effortless “yes, I live in SoHo” look. Bonus: look iconic with scrunched socks and a coffee run.
UGG® Tasman II for Women
The Bailey Bow’s cool little cousin—tiny boot, big vibe. They’re the boots you throw on with jeans, sweats, or a miniskirt, instantly pulling the whole outfit together while keeping you cozy. These are the actual ones I actually have.
Women's Classic Ultra Mini Platform
Mini Skirts
Pleated, plaid, and shorter than your principal thought was “appropriate.”
The “going to the movies in 2004” skirt—add tights + UGGs for main-character energy. It’s giving popcorn bucket, Gossip Girl reruns, and the kind of confidence that makes you think you could win Prom Queen.
Leather-effect mini-skirt - Women
A glossy lil’ throwback that makes every sweater instantly cooler. Picture yourself layering it with a slouchy knit, knee-high boots, and an overstuffed hobo bag—you’re basically in a Hilary Duff movie montage.
Women's Leather Skirts
Prep-school Y2K, but make it 2025. It’s plaid perfection that pairs with knee-high socks, layered tanks, and the kind of chunky highlights Paris Hilton would approve of.
Mini Skirt Collection
A total 2000s throwback—flirty pleats, mini length, and built-in shorts for comfort. Perfect with a baby tee and chunky belt for mall hangs, or layered with knee-high socks and a hoodie for crisp fall days.
Women's Mid-Rise Pleated Mini Skort
Flirty, flouncy, and warm enough to fool your mom into thinking it’s “practical.” A sweater knit mini with circle-cut volume that makes every hallway your runway.
Mid-Rise Circle-Cut Sweater-Knit Mini Skirt
Outerwear
From faux-fur trims to puffers so big you could star in a Hilary Duff snow day movie.
Lindsay-leaving-the-club leather—cropped, tough, timeless. It’s the jacket that instantly adds edge, whether you’re just grabbing a PSL or pretending you’re stepping into a Maxim shoot circa 2003.
Women's leather jackets 2025
Tiny but mighty. Cropped, zip-up, and made for apple picking selfies. Looks like something your fave Disney Channel star would wear on a ski trip episode.
Women's Sweater-Knit Mini Puffer Jacket
THIS IS THE COAT I WORE AT AGE 8
Juicy Couture Orange Satin Puffer Down Jacket XS
Belts & Bags
Bedazzled buckles and tiny purses that barely fit a Razr—aka essential.
Pop-punk polish for low-rise denim. It’s the belt every MySpace queen wore with chunky highlights, heavy eyeliner, and a camera flash pic in her bathroom mirror.
Weekday wide eyelet belt in black
A glossy little baguette moment—very “flip phone in the slip pocket.” The kind of bag that makes you want to walk Fifth Ave like it’s your runway, pumpkin spice latte in hand.
Sam Icon Shiny Small Convertible Crossbody | Kate Spade New York
If your fall is “work by day, hot cocoa by night,” this carries both. It’s giving Carrie Bradshaw meets office intern: chic enough for the subway, practical enough to hold your entire life.
Sam Icon Large Tote | Kate Spade New York
Jewelry
Hoops so big they touched your shoulders, charms for every crush, and rhinestones that could blind in homeroom lighting.
Sweet, stackable, and reads like a yearbook doodle. It’s the necklace equivalent of writing your crush’s name in glitter gel pen and circling it with hearts.
Ari Heart Collection
Paper-clip chain that layers perfectly over baby tees. It’s the grown-up version of engraving your initials on a Lisa Frank notebook—personal, sparkly, and begging to be layered.
Vintage Alphabet Parker Charm
A little Brit-it-girl energy—chunky but not loud. It’s got the perfect “Kate Moss leaving a party with eyeliner smudge” aura, but subtle enough for your Zoom call.
Lucy Williams Large Ridge Cross Necklace | 18k Gold Vermeil
Class-ring vibes, grown-up execution. Think senior-year energy but with 2025 polish—you can even get it engraved for that custom nostalgia-core moment.
Engravable & Diamond Signet Rings
Big enough to make a statement at the mall, elegant enough to keep during dinner with your folks. These hoops float between Y2K princess and modern grown-up—perfect with a low ponytail, glossed lips, and that girl who plays The Neighbourhood on repea...
Hoop Earrings