Dan Humphrey was the outsider looking inon the scandalous lives of Manhatten's elite. A proud Brooklyn resident, Dan displayed a quirky style that was more individualiz… See more

Like Dan, Vanessa was an outsider to the Upper East Side group in Gossip Girl. Her stylistic choices reflected this; many of her outfitswere vibrant vintage pieces that highlighted … See more

Nate Archibald's style was simpler than his peers but no less stylish. During the first season, Nate is usually seen in his St. Jude's uniform. The Archibald heir is the antithesis o… See more

Serena often stole the show with her fashion choices, but the socialite had to contend with her mother to be the best-dressed Van der Woodsen. Lily was a glamorous … See more