By Alexus Mosley

The Upper East Side isn’t just a zip code, it’s a vibe, a lifestyle, and for fans of Gossip Girl, a never-ending source of style inspiration. From polished preppy looks to bold statement pieces, the fashion of Manhattan’s elite teens is equal parts timeless and trend-setting. Whether you’re channeling Blair Waldorf’s head-turning elegance or Serena van der Woodsen’s effortlessly chic allure, these Gossip Girl–inspired fashion trends will have you feeling like the ultimate main character.

1. Headbands: The Ultimate Upper East Side Accessory

No Gossip Girl outfit is complete without a statement headband. From classic pearls to bold, embellished pieces, headbands instantly elevate any ensemble. Whether it’s a preppy blazer, a cozy sweater, or a chic party dress. Think Blair Waldorf: polished, confident, and effortlessly glamorous.

Style Tip: Layer a thin metallic headband under a thicker, embellished one for extra drama, or match your headband to your outfit’s color palette for a perfectly coordinated Upper East Side vibe.

2. Tailored Blazers & Structured Outerwear

Blazers aren’t just for work. They’re a Gossip Girl staple. Pair a perfectly tailored blazer with a plaid skirt or high-waisted trousers for that preppy luxe energy. Outerwear like camel coats, trench coats, or cropped jackets adds a sharp, polished finish that’s effortlessly chic.

Style Tip: Choose classic neutrals for daytime sophistication, or experiment with bold patterns and textures for evening glam.

3. Statement Accessories

From oversized sunglasses to designer handbags, accessories are everything on the Upper East Side. Pearls, chunky necklaces, and designer shoes take even the simplest outfits to elite status. Accessories are your way to say, “I’m stylish, I’m confident, and yes, I belong here.”

Style Tip: Mix metals and textures for depth, or use a signature bag or shoes as the focal point of your look.

4. Preppy Meets Edgy

It’s all about balance. Leather skirts, jackets, or boots can transform a classic plaid skirt or silk blouse into something unexpectedly modern. The key is combining traditional prep with daring textures or patterns to show confidence and individuality.

Style Tip: Pair a classic tweed skirt with a leather moto jacket, or layer contrasting fabrics like silk and knitwear for a textured, fashion-forward ensemble.

5. Mini Dresses & Skirts

Gossip Girl girls know that length matters. Mini skirts and dresses are perfect for layering with tights, boots, or sleek heels. These pieces maintain a youthful, flirty, and totally Instagram-worthy look.

Style Tip: Opt for structured silhouettes during the day and sequins or metallic fabrics for evenings out—always seasonally appropriate and effortlessly chic.

6. Colored tights

From vibrant jewel tones to playful pastels, this trend brings youthful energy to preppy ensembles while keeping your style unmistakably chic.

Style Tip: A little color goes a long way. Sometimes all you need to elevate a classic and neutral look is a bright pair of tights.

Gossip Girl fashion is about confidence, polish, and putting your personal stamp on every outfit. Whether you’re a headband devotee like Blair or a carefree style queen like Serena, these trends prove that Upper East Side style is timeless, aspirational, and effortlessly chic. Layer, accessorize, and don’t be afraid to mix preppy classics with bold, modern twists. Because, in true Gossip Girl fashion, drama is always part of the outfit.

6 Fashion Trends Gossip Girl Inspired: How to Dress Like an Upper East Side Icon