Your Guide to Dressing Like a Gossip Girl. XOXO, A Style Set

From Blair’s polished preppy looks to Serena’s effortless cool girl aesthetic, Gossip Girl gave us look after look. Whether they’re sitting on the steps of The MET, or headed for a night out in Manhattan, these Upper East Siders knew how to style. Here’s the gossip to dressing like your favorite Gossip Girl character.

 

Button Downs:

Throughout their school days, Blair, Serena, and even Jenny wore a classic button down. Whether they styled it more loosely and flowing like Serena, or buttoned to the top in classic style like Blair, a button down is an essential staple in any Upper East Sider’s wardrobe.

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Pants:

In true 2000s chic fashion, Blair and Serena could be spotted in skinny jeans. Paired with a sweater and a chunky necklace, the perfect pair of slim fit pants was any Gossip Girl’s version of a casual look. To get the modern-day look, style your skinny jeans with high boots, a fitted sweater, and an oversized blazer or leather jacket.

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Skirts:

Flowy and fun, the New York City it-girls showed off their personality with a wide range of skirts. Whether you lean more boho like Serena, preppy like Blair, or classic like Lily, skirts are a great way to bring in feminine flair to your wardrobe!

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Patterned Dresses:

Upper East Siders were never afraid of being bold. They loved dresses with prints like florals in the warmer months, and they leaned into plaids and houndstooth in the cooler months. Still showing personality and color, prints are a perfect way to spice up your wardrobe!

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Winter coats:

For a walk through Central Park, Blair and Serena could be spotted in a variety of winter coats. Typically leaning towards either a short coat or a pea coat with patterns and bold colors, the right jacket always completed their winter outfits.

 

Statement Bags:

The perfect accessory to any outfit is a bag. For the Gossip Girls, it was more than just a practical addition, it was a statement. From Blair’s polished, classic, structured classics to Serena’s boho breezy style, the right bag adds personality and completes your outfit, fit for walking the streets of manhattan. 

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Hair Accessories:

No true Gossip Girl outfit is completed without a hair accessory. Whether you lean towards Blair’s iconic headbands or Serena’s hair clips, an accessory is the perfect way to tie together your outfit. 

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