Whether she's crowned in a power headband or wearing scads of oversized pearls, Leighton Meester's primetime alter ego—Gossip Girl's peerless Blair Waldorf—is adored for her prep-princess look. But while Meester is well known (and rightfully worshiped) for her screen-stealing character's fantastic outfits, frankly, the actress's personal style is much more intriguing. Though she works her character's amped-up UES look very well, in real life, Meester consistently demonstrates her ability to execute edgier ensembles with sophisticated flair. In fact, Meester manages to dance upon the fine line between directional and disappointingly trendy—a very difficult balancing act, indeed—without ever veering into fashion-victim territory. Plus, and perhaps most of all, we appreciate the way she consistently supports emerging talent, opting for designers like Christian Cota, Christopher Kane, and Emilio De La Morena for her red-carpet moments.