Perhaps taking a page out of Blair's book, Leighton takes the plunge in this stunning Prada dress.
In an LBD with a furry twist, Leighton rocks the red carpet in Louis Vuitton at an amfAR New York Gala to kick off Fall 2012 Fashion Week.
This strapless Balmain minidress doesn't leave much to the imagination, but it certainly could incite plenty of talk at the celebration of Gossip Girl's 100th episode.
The Gossip Girl star wears a petaled blouse and skirt by Jason Wu, plus sexy strappy Jimmy Choos, to celebrate Nan Goldin's photography for Jimmy Choo's Icons Collection.
Leight gets girlie in an off-the-shoulder frock by Christian Dior at the designer's spring 2012 show in Paris. Of course, we can't forget to mention those killer Louis Vuitton Mary Janes she's rocking.
The HTC Product Launch event at the Highline Stages brings out the daring side of this fashionista, but her Marios Schwab dress and beaded Burberry heels just don't mesh well.
This auburn bombshell makes vintage chic look effortless in an outfit by Alexander McQueen paired with a brown leather belt and animal-print heels.
The star looks like she's on cloud nine! This Carven dress makes her look heavenly, with a little extra help from some Tiffany & Co. jewels and Roger Vivier flats.
There's no wondering why this Gossip Girl star is the face of Vera Wang's new fragrance! She looks magnificent in this yellow belted Vera Wang dress.
Not only is the actress rocking her new, bangin' auburn haircut, but she's also looking summery and cute as a button in this formfitting Carven off-the-shoulder printed dress with Alexandre Birman strappy sandals and Yves Saint Laurent tote.
The Gossip Girl fashionista rocks these Vera Wang leather trousers, a beige flowy top, Brian Atwood strappy heels and Dannijo jewelry.
Leighton is stunning in this shiny silver Balmain mini, Pierre Hardy shoes, Paco Rabane bag, and Bulgari jewels at the MTV Movie Awards.
During New York fashion week, the starler wears this '70s-printed polka-dot dress and strappy red shoes. Fashion people may get away with wearin crazy outfits to fashion week, but the usually ardorable actress looks frumpy in this otufit.
The Gossip girl looks chic 'n' smart in a Giambattista Valli top and skirt at the Apple SoHo store, but what we really covet are those fab leopard-print Brian Atwood heels. Love!
The Nylon cover girl hits the mag's New York City bash in a Proenza Schouler dress with sheer black overlay and black heels—which, incidentally, is the same dress K.Stew rocked on the cover of Vogue.
What a blooming beauty! The actress's floral-print Emanuel Ungaro mini with Pierre Hardy sandals at the Jimmy Fallon studios is coming up roses.
Leighton covers up in a leather and jersey Michael Kors maxidress at the NYC premiere of The Roommate.
The actress channels the '20s in a fringed Louis Vuitton frock at a gala in Los Angeles.
Looking ultrafemme in a high-neck printed dress by Burberry Prorsum and killer Jimmy Choos, the actress sets herself apart from the other stars at the 2011 Golden Globes.
Leighton's all leggy in this curve-hugging blue mini, but the floppy black booties and Halloween makeup throw off the entire look.
Leather, a high neckline, awkward sleeves...what more could you ask for? At the end of the day, we're still not sure what to make of this Louise Golden minidress Ms. Meester wore to the Z100 Jingle Ball.
Looking pretty in pink at a screening for Country Strong, Leighton opts for a Christian Dior multistrand minidress and orange Lanvin shoes.
The actress suits up in a Thom Browne ensemble at the Gotham Independent Film Awards in NYC.
Quick, Leighton, fire your stylist before you subject us to another fashion faux pas! The starlet graced us with this, um, peculiar see-through lace Marchesa jumpsuit (they still make those?) at an event for Harry Winston.