1. CW breakout star Jessica Szohr breezes through 5 of her best and worst looks, explains how Gossip Girl revolutionized her style, where to get the best bargains and more, when we ask her, "What Were U Thinking?"

More On Jessica's Style

  1. From bohemian beauty to rock and roll edgy, see how Jessica's style has evolved in our photo recap!

  2. Jessica tells us about her outfit - most of which is from Urban Outfitters and Top Shop.

  1. Jessica critiques a "fun, easy and comfortable" Alice + Olivia ensemble she rocked in '08.

  2. Jessica explains why topping an outfit with a beanie works all year round.

About Jessica Szohr

What would happen if we took your favorite fashionable celebs, showed them five outfits they've worn out in public over the years, and asked them "What Were U Thinking?" You're about to find out!

This week, we're asking actress Jessica Szohr. Jessica grew up in small-town Menomonee Falls, Wisconsin, modeling and doing commercials from the early age of six. After graduating from High School, Jessica made the move to L.A - where her bright smile, exotic looks (she's half-Hungarian and quarter African-American) and uber-chill attitude, made her a standout.

Jessica scored several roles on shows like CSI:Miami, What About Brian, and Joan of Arcadia before landing in one of the hottest (and most stylish) shows today – The CW's Gossip Girl.

Jessica was cast as Brooklynite Vanessa Abrams – the best friend to Dan Humphrey and an aspiring filmmaker. Vanessa's character has a quirky, eclectic style - often accessorized with doorknocker earrings and limited-edition Dunks. Her "hipster" look is a far cry from the preppy chic wardrobe of her cast mates – who play resident teens on the Upper East Side. While the characters may be fashion worlds apart – Jessica's real-life style is undoubtedly influenced by ALL of the Gossip looks.

Gossip also brought Jessica to New York City – their filming location and now home. With New York City being the central location for major fashion events, trend-starting shows and of course - unique street style, it was hard not to make an impression. Jessica began to take more risks, explore new looks, and hit red carpets with confidence – wearing everything from flowy florals to rocker studs to elegant "grown-up" gowns.

With Gossip Girl now in it's fourth season and a new movie due this summer - Piranha 3-D, Jessica continues to rock tabloid-worthy looks and we're confident there’s many more to come.

Past Guests

  1. We asked Ashley Greene 'What Were U Thinking?' on October 12. Watch the episode now!

  2. We asked Nelly Furtado 'What Were U Thinking?' on September 28. Watch the episode now!

  3. We asked Kim Kardashian 'What Were U Thinking?' on September 21. Watch the episode now!

  4. We asked Kristin Cavallari 'What Were U Thinking?' on September 9. Watch the episode now!

  5. We asked Keri Hilson 'What Were U Thinking?' on August 24. Watch the episode now!

  6. We asked Adrienne Bailon 'What Were U Thinking?' on August 10. Watch the episode now!

  7. We asked Kelly Osbourne 'What Were U Thinking?' on July 27. Watch the episode now!