Gossip Girl Fashion
1/22On a quick shopping trip downtown in Nolita with her best friend Blair, the ever-cool Serena knows how to keep it low-key for day with a denim vest over a tank and gray skinny jeans. Always letting her hair down, Serena rarely wears an updo, which adds to her relad look.
2/22From the moment 's Upper East Side. Always attending functions, Serena knows how to brush up properly while remaining true to her free-spirited take on fashion. Brunch at the Palace just wouldn't be acceptable without a light, airy dress such as this floral-print number.
3/22Taking a break from the set of . She paired dark-wash denim with a white top and a Miu Miu handbag —a choice most likely too conservative for her TV counterpart. But her green jewelry added a pop of color that Serena would surely approve of.
4/22Blake arrived at MTV's wearing a playful Vena Cava jumpsuit, which Serena would give a stamp of approval. She carried a Miu Miu bowler bag and donned classic Christian Louboutin heels.
5/22Uptown-chic met downtown-cool when Blake wore a lace Chanel bubble dress to the Tribeca Film Festival in April 2008.
6/22Elegant at the Met's Costume Institute Gala in May 2008, sophisticated Blake glammed it up in a feathered Ralph Lauren gown, proving that this glamour girl, like her on-screen doppleganger, has a flair for the dramatic.
7/22From the first episode of , Leighton Meester's character, Blair Waldorf, has had a distinctively feminine and classy style. Headbands and frills have become her trademark. Blair attended brunch in a prim and proper white floral eyelet dress, topping it off it with pearl bracelets and the ever-present headband.
8/22A trendsetting look for both her on-camera cronies as well as prep-school students everywhere, Blair's signature bright tights and headband combo make an early appearance in . Paired with flats, her school uniform and a matching cardigan and handbag, Blair is the quintessential Upper East Sider.
9/22A far cry from Blair's wardrobe choices, Leighton's red-carpet style is much trendier and experimental than Blair's typical ruffles. Appearing in a simple gray Missoni dress to the premiere, Leighton's clean look turned heads.
10/22At a CDFA/ Fashion fund party, Leighton poses with designer Jason Wu in a soft dress that Blair herself might consider. The delicacy of the fabric and neutral tones make for sophisticated yet youthful garb but still maintain Blair's required dose of Uptown class.
11/22Back on the set of , Blair donned a floral Collette Dinnigan trapeze dress for season one's wedding scene. Though it's predictable Blair with the headband and flowers, it's far more formal and delicate than her day-to-day look.
12/22Appropriately going glam in a yellow YSL dress, Leighton made an appearance at the Metropolitan Opera opening of La Fille du Régiment, combining her penchant for slimming silhouettes with Blair's love of designer duds.
13/22The girl with by far the quirkiest closet on phenomenon not only reserved for the the infamous Blair—Vanessa also joins in on the trend. Blue tights, with a geometric-patterned dress, a bright orange coat, a patterned scarf, teal hoop earrings, and tan moccasin boots, Vanessa's outfits push the border of wacky, but always remain on the right side of cool.
14/22Outside of , Jessica's style is much more toned down than Vanessa's. At Longchamp's 60th Anniversary party, the starlet opted for solid colors, giving her outfit a tougher edge.
15/22Much like her on-screen character, Jessica looks playful and edgy. She wore a hat and heels with her V-neck and cut-off denim shorts to the Stand Up For A Cure concert with Dave Matthews Band.
16/22Fashion united Jessica with friends Blake Lively and Penn Badgley at the store opening of Juicy Couture on Fifth Avenue. Jessica glowed in her bright green Juicy dress. The loose cut of the dress and her long, wavy hair showed the actress' flower-child side. The fabulous addition of a thin black belt and matching ankle boots give her outfit an edgy punch that made an impact and wowed the crowd.
17/22Jessica, usually a bit rough around the edges in the trendiest way possible, can do the formal thing, too! Wearing a J. Mendel gown, she attended A Magical Evening Gala in November, looking fantastic. The off-white, floor-length dress hugged her curves and showed her ladylike side. Jessica even pulled back her usually untamed hair.
18/22Little Jenny Humphrey, the eager character played by Taylor Momsen, strives to be one of the gang by donning bright tights, patterned socks, and the oh-so-essential headband. From the start, Jenny struggled to find herself amidst high-school hazing.
19/22Slowly breaking away from her school-dictated style, Jenny tones down the ultragirly, ultrapreppy look for something a little bit wilder. No longer wearing headbands in abundance, Jenny looks less prep-school and more city girl. Her blue overcoat looks cool with this patterned scarf.
20/22Ultrafeminine in a light yellow Marchesa dress at the FiFi Awards, Taylor's red-carpet style is much more classic than Jenny's look.
21/22Taylor rocks her new tough look in a red dress and leather leggings at a screening of Gus Van Sant's film . This edgy girl is a far cry from little Jenny Humphrey, who started out on the steps of the Met with Blair and her cronies.
22/22After the sudden transformation of Jenny's look on , Taylor quickly followed suit. With a palette shift and more rock 'n' roll pieces like a leather jackets and Converse sneakers, Taylor, like Jenny, begins to dress more downtown-chic than uptown schoolgirl.
