Style File № 18

How to dress like Serena van der Woodsen from Gossip Girl

Flowing fabric, undone hair, and a slip dress that looks thrown on but never is. Here is how to build it.

Boho Maxi DressLoose WavesFringe BagLayered Gold JewelryEffortless Layering

Late-2000s Upper East Side 4 pieces 2 looks

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№ 18 Gossip Girl Undone on purpose, expensive underneath. Serenavan der Woodsen Effortless bohemian It girl. Late-2000s Upper East Side 4 pieces Boho Maxi Dress · Loose Waves · Fringe Bag

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The Wardrobe, Decoded

Undone on purpose, expensive underneath.

Serena's whole look is engineered effortlessness — loose maxi dresses, soft fabric, minimal jewelry, hair that looks air-dried but isn't. Where Blair is armor, Serena is ease. Build from flowing silhouettes and let the rest fall into place.

01

The Drape

Rooftop parties, uptown
01 Flowing Boho Maxi Dress Soft, lightweight fabric that moves — the base of every Serena look. Budget Splurge
Splurge Price on Amazon Flowing Boho Maxi Dress Flowing Boho Maxi Dress Sold on Amazon Budget Price on Amazon Flowing Boho Maxi Dress Flowing Boho Maxi Dress Sold on Amazon Piece finder Find this piece for me We'll match it on Amazon — cut, colour and collar already filtered. Find it
02 Fringe Suede Crossbody Bag Slouchy, worn across the body, never fussed over. Budget Splurge
Splurge Price on Amazon Fringe Suede Crossbody Bag Fringe Suede Crossbody Bag Sold on Amazon Budget Price on Amazon Fringe Suede Crossbody Bag Fringe Suede Crossbody Bag Sold on Amazon Piece finder Find this piece for me We'll match it on Amazon — cut, colour and collar already filtered. Find it
In this look 2

pieces · current prices are shown on Amazon

02

The Finish

Never overdone
01 Layered Gold Chain Necklaces Thin, mixed lengths, worn together and never removed. Budget Splurge
Splurge Price on Amazon Layered Gold Chain Necklaces Layered Gold Chain Necklaces Sold on Amazon Budget Price on Amazon Layered Gold Chain Necklaces Layered Gold Chain Necklaces Sold on Amazon Piece finder Find this piece for me We'll match it on Amazon — cut, colour and collar already filtered. Find it
02 Oversized Aviator Sunglasses Gold-frame, worn pushed up or on — the signature accessory. Budget Splurge
Splurge Price on Amazon Oversized Aviator Sunglasses Oversized Aviator Sunglasses Sold on Amazon Budget Price on Amazon Oversized Aviator Sunglasses Oversized Aviator Sunglasses Sold on Amazon Piece finder Find this piece for me We'll match it on Amazon — cut, colour and collar already filtered. Find it
In this look 2

pieces · current prices are shown on Amazon

Written and edited by · Updated 17 July 2026

Filed under 2000s Gossip Girl Boho Luxe

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