Nostalgia Chic: A 2000s Fall Fashion Guide
Step into fall with iconic looks inspired by your favorite early-2000s TV shows — from plaid skirts to leather jackets and everything in between.
by Bree Lauder-Williams ★ October 30th, 2025
Design by: Christina Liguori
Fall is the season of Halloween, coffee runs and most importantly, the long-awaited return of 2000s fashion. From the iconic plaid sets of “Gossip Girl” to the timeless henleys of “The Vampire Diaries,” early-2000s style is cozy, chic and perfect for crisp, autumn weather. Honestly, it’s the ideal excuse for a thrift haul (or a deep dive through your own closet) — just promise to leave the turquoise and peach in 2006, where they belong. Here’s how to dress like your favorite fall TV icon — without looking like you’re in costume.
Gossip Girl
Hello, Upper East Siders. The drama, the secrets, the fashion — “Gossip Girl” defined an era. From Blair Waldorf’s preppy perfection to Serena van der Woodsen’s effortless it-girl glam, every outfit was a statement. Fall is the perfect time to channel that Manhattan chic. Think bold tights, tailored layers and a little luxury. On the Upper East Side, fashion isn’t just what you wear — it’s who you are. To emulate Blair, pair a plaid skirt with a tailored jacket, add statement tights, pearls and of course, a designer headband. If Serena is more your style, layer a few jackets with a silk scarf, grab a statement bag and slip into heeled booties for that effortlessly polished look. For those who love a little edge like Little J, mix prints, throw on statement boots and don’t be afraid of bold accessories. Essential fall staples for this look include blazers, silk blouses and cardigans up top, with plaid or mini skirts for bottoms. Finish the look with knee-high boots, heeled booties or loafers. And don’t forget to accessorize with headbands, statement handbags and scarves.
Pretty Little Liars
Got a secret? You should probably keep it. “Pretty Little Liars” ruled the early 2010s with friendship, mystery and killer outfits. Each “Liar” had her own distinct vibe — Spencer’s preppy polish, Aria’s artsy thrift-core, Hanna’s glam and Emily’s sporty edge.
Together, they mastered layered fall fashion with denim, boots and statement jackets. To channel Alison, go for designer jeans with a ruffled tank top and a pair of wedge heels. For Aria’s eclectic, artsy look, mix lacy tights and a denim skirt with a bold top, leather jacket and standout jewelry. Emily’s sporty aesthetic calls for denim shorts, a lightweight long-sleeve and combat boots, while Hanna’s glam wardrobe shines with peplum tops, skinny jeans and a leather jacket finished with heels and a statement handbag. For the academically chic Spencer, pair a plaid skirt with a tailored blazer, a crisp collared shirt and loafers. Finally, don’t forget a designer handbag to pull it all together!
Layered sweaters, cardigans and statement jackets are the go-to tops for this look, while fitted denim skirts or jeans complete the base. Finish with leather or ankle boots, or elevate the outfit with heels. A scarf, belt or a bold piece of jewelry adds that finishing touch of mystery.
The Clique Series
A little more niche but no less iconic, “The Clique” defined Y2K prep. Massie Block and the Pretty Committee set the trends — and the rules — with confidence and couture. If you don’t want to be an LBR (Loser Beyond Repair), here’s how to keep up with OCD’s (Octavian Country Day) elite this fall.
In the Fall Fashion Edition of the Pretty Committee’s “Current State of the Union,” soy chai lattes are definitely in while lemonades are out. Glossy “Glossip Girl” lips are trending, Juicy Couture sweatsuits are a thing of the past, knee-high boots reign supreme over Vibram FiveFingers and charm bracelets have replaced the once-popular ribbed tanks.
To dress like Massie, try pairing a BCBG tank top with a chic mini skirt and stylish tights, then finish the look with designer ballet flats or knee-high boots. Alicia’s effortlessly sophisticated vibe shines through a vintage Ralph Lauren blazer, fitted jeans and dressy sandals. Dylan embraces bold color in a Moschino dress layered with an Alice + Olivia jacket and accessorized with a Michael Kors handbag, while Kristen leans into cozy preppy with a plaid skirt, layered tops, a jacket and a knit hat to tie the look together.
For this aesthetic, focus on chic tanks and structured blazers paired with tailored jeans or pleated skirts. Ballet flats or heeled boots strike the perfect balance between polish and playfulness. To complete your Pretty Committee look, accessorize with charm bracelets, headbands, and structured handbags — because when it comes to “The Clique,” being fashionable is always in.
The Vampire Diaries
Dear diary, something about Mystic Falls will always feel like fall. The warm colors, the mysterious mood and the leather jackets perfectly capture that autumn vibe. Whether you’re more of an Elena (casual and comfy) or a Katherine (dark and daring), this show’s aesthetic never misses. To capture Elena’s easygoing style, wear a long-sleeve henley with skinny jeans and Converse, but don’t forget her signature vervain necklace. If you’re feeling more like Katherine, lean into her edge with a fitted leather jacket, lace blouse and low-rise jeans, paired with knee-high boots for the ultimate confident statement. The Vampire Diaries looks thrive on fitted jackets, velvet blouses and henleys for tops, paired with classic skinny jeans. Ankle or tall leather boots and subtle jewelry like a simple necklace or scarf make every outfit feel mysterious yet wearable.
The Thing in This Article to be Nostalgic About: Key Takeaways
Whether you’re sipping lattes on the Upper East Side, guarding secrets in Rosewood, ruling the halls like Massie Block, or chasing supernatural drama in Mystic Falls, early 2000s fashion is back — and it’s ready for fall. So grab your boots, layer your knits and channel your inner it-girl. XOXO.
Edited by: Ava Ascenzo