Sneak Peek: Gossip Girl On-Set Style

The stylish Gossip Girl cast makes for a delicious mix of plaid and khaki on the steps of their Upper East Side private school.

Blake Lively adds a touch of California cool to her character Serena van der Woodsen’s preppy plaid uniform with flat Loeffler Randall boots, a leather jacket and a Katherine Kwei handbag.

The onscreen BFFs are perfectly in step with stylish coats and bags. Lively hits her stride in a tight Just Cavalli coat and Valentino bag while Leighton Meester, as Blair Waldorf, totes a Ralph Lauren purse and a blue trench coat.

Though Serena may be over her posh Upper East Side lifestyle, it doesn’t stop her from roaming the city in luxe boots and the must-have Burberry Warrior Bag.

Chace Crawford, as dreamy Nate Archibald, ditches his uniform tie and goes casual in jeans, a brass button Ralph Lauren coat and penny loafers.

Sporting a new comb-back and slick suit, a rain-soaked Chace Crawford gets ready to film a love scene with his onscreen girlfriend Meester.

Ed Westwick plays resident villain Chuck Bass superbly in a devilish red coat over his classic khaki uniform.

Out with the old and in with the new! Taylor Momsen takes center stage as Jenny Humphrey on the steps of the Metropolitan Museum of Art in her canary yellow trench and hot pink Anna Corinna tote.

The youngest cast member adds some style to her preppy plaid with loud purple leggings and a pom-pom cap.

She may not have the swanky Upper East Side address, but Brooklyn’s finest Humphrey has the bag! The freshman totes a pricey purple Valentino purse – sure to make Blair Waldorf jealous!– with a yellow trench and sweet patent heels on her way to school.

Channeling her character’s icon – Audrey Hepburn – Leighton Meester soaks her belted trench and Louboutin T-strap pumps in a homage to the classic last scene of Breakfast at Tiffany’s.

Losing a crown never looked so fashionable! The fallen queen goes patriotic in her red Zypher tights, navy uniform, Tory Burch flats and Foley & Corinna bag.

Not content with carrying just one fabulous bag, Meester dons two patent numbers – one from her offscreen favorite Felix Rey – with her cozy Pencey T-shirt and striped Tory Burch cardigan.

Michelle Trachtenberg proves she sure can keep up with the Joneses by carrying an oversized black python Gucci “Hysteria” bag with her J Brand jeans – watch out Blair and Serena, here comes competition!

Taking the town in style, Trachtenberg films a scene on the cobblestone streets of the Meatpacking District in a LaRok studded top, oversized earrings and red patent heels.

Seems like Serena has more to worry about than the newbie’s wardrobe. A casually dressed Trachtenberg might have her sights on something a little more important – Dan!

As Brooklyn boy Dan Humphrey, Penn Badgley looks like he took a page out of The Preppy Handbook – bedhead and all! – while filming on the Upper East Side.