For four seasons, Gossip Girl has provided us with addictive drama, numerous surprises (Lady Gaga, anyone?), and—undeniably—great clothes. Our favorite Upper East Siders have come a long way from their school uniforms of the first and second season, each further developing their own distinct style.
Although it was difficult to locate a photo of every great outfit from the show, I compiled some of the best looks of the show’s most notably fashionable characters: Blair, Serena, Jenny, and Chuck.
“I love your Louboutins, but the bow goes on the right.” With a fashion designer as a mother, Blair lives up to any expectations of having incredible style. She favors classic, timeless items, generally opting for well-fitted garments with conservative cuts. She adorns her outfits with feminine detailing, such as bows, lace, or pearls.
Serena van der Woodsen
Serena upholds her bombshell reputation with her body-conscious outfits, always showing just the right amount of skin. She never looks like she’s trying too hard since her hair and makeup are usually more casual. Bold accessories (statement necklaces, large handbags, etc.) add extra flair to her fashion-forward pieces, but they’re used in moderation to avoid excessiveness.
Chuck adds a creative twist to Ivy League style when not wearing a traditional suit. He’s worn tailored jackets and pants in a variety colors and fabrics, unafraid to mix patterns and wear bold colors. He frequently wears bowties, and even donned an ascot. In season four, we see him adopt European-inspired looks, probably from being in France. And the cane? He’s Chuck Bass, so he pulls it off.
The transformation from daddy’s girl to Queen B is quite evident in Jenny’s change in style. The innocent pigtails of season one are replaced with heavy makeup, dark colors, and occasionally even fishnets. Her edgy look calls for short skirts or shorts paired with some type of hosiery. I can’t recall ever seeing Jenny wear flat shoes or pants.