Sixteen years ago, Gossip Girl revolutionized the world of television and forever transformed our fashion sensibilities. Many devoted fans still cherish their collection of Gossip Girl-inspired ensembles hanging in their closets—attires that effortlessly evoke the essence of a genuine Upper East Sider whenever they’re flaunted. And, of course, no outfit is complete without a headband that would make Blair Waldorf herself nod in approval.
It’s undeniable that the debut of Gossip Girl unfolded over a decade and a half ago. While we frequently reminisce about the captivating plotlines set in Manhattan (with occasional escapades in Brooklyn), the intricate love triangles, and the extravagant events that graced each of the six seasons, it’s the enduring impact of the show’s iconic fashion moments that continues to resonate. Blair Waldorf’s sophisticated capes, coats, and signature headbands left an indelible mark on a generation, while Serena van der Woodsen embraced a bohemian allure with her free-flowing dresses and eclectic, dangling jewelry.
The distinct styles of each character quickly captivated the audience. Numerous esteemed designers contributed their creations to the show, prompting former Gossip Girl costume designer Eric Daman to reveal to Fashionista, “Throughout the six seasons, Blair never repeated a headband, and Serena never stepped out in the same pair of shoes or carried an identical bag.” Such unwavering dedication to fashion was a testament to the times—especially in an era that predates the dominance of Instagram.
As with all matters of fashion, some looks have aged gracefully while others have taken a back seat. (Rainbow-hued tights while strolling down Fifth Avenue might not be on our fashion agenda anytime soon, apologies to Blair and her Constance comrades.) Yet, even after all these years, certain gala gowns and meticulously designed school uniforms worn by these privileged New York adolescents retain a timeless allure that seamlessly integrates with contemporary styles.
In homage to one of television’s most iconic showcases of style, here are 18 Gossip Girl ensembles that would exude the same level of chic sophistication on the steps of the Metropolitan Museum of Art today as they did in 2007—alongside a selection of items that are readily available for purchase in 2023. Sending fashionable regards, XOXO!
- Serena’s Stylish Wanderlust
Spotted: The inaugural ensemble sported by Serena van der Woodsen in the series—undoubtedly one of her perpetually elegant looks up till now. The airy jacket, Breton-stripe blouse, and denim jeans coalesce into a quintessential #OOTD. A closer inspection reveals the artful addition of a neck-tied scarf by none other than S. Truly, a timeless embodiment of class.
2. Blair’s Elegance Embodied in a Scarf
Evidently, Gossip Girl anticipated the bandanna-as-necktie trend well ahead of its time. Blair’s verdant scarf impeccably harmonizes with her unmistakable “Can you sense my impending Hamptons getaway?” attire. In totality, the enduringly flawless maritime motif woven into this ensemble remains an exquisite choice for the spring season. The sole aspect that might warrant reconsideration is the inclusion of the white belt.
3. Blair’s and Serena’s Back-Baring Sheaths
The enduring charm of coordinating with your closest confidante remains eternally chic. Let’s not overlook the allure of these open-back sheaths and gleaming metallic pumps, seamlessly aligning with contemporary fashion currents. Regrettably, the precise Eleanor Waldorf creations are beyond our reach, yet there’s certainly no impediment to donning these ensembles in 2023 and radiating impeccable style.
4. Serena’s Radiant White Soiree
At the Hamptons White Party, the attire directive was refreshingly clear-cut. Nonetheless, Serena effortlessly eclipsed all attendees, including Nate, who sported a modest white tee and sneakers. As the impending arrival of summer beckons, it’s a timely cue to amass a collection of white ensembles and flowing maxidresses, poised for unveiling once the mercury rises.
5. Berets: Blair’s New Crown
During the second season, Blair made a daring shift from her signature headbands to embrace berets—well ahead of Maria Grazia Chiuri’s showcase on the Dior runway. No surprises here, Blair was always a step ahead in setting trends. So, why not consider reintroducing this French flair into your own fashion repertoire? It’s undoubtedly a distinctive style, and there’s no doubt you can rock it with confidence.
6. Blair and Serena’s Classic Hamptons Elegance
Enter B. and S. into the Hamptons scene! Their second-season rendezvous was an absolute style sensation. Serena’s sleek mini slip dress wouldn’t feel out of place on today’s seaside outings. Meanwhile, Blair’s impeccable taste in handbags was evident: She gracefully sported a wicker rendition of the Kate Spade New York “Sam” bag, a design that has gracefully resurfaced more than once.
7. Serena’s Bold Outerwear Choice
While traversing the streets of Paris, S. effortlessly slips into her most vibrant and attention-commanding outerwear. This metallic statement jacket possesses the enduring ability to complement vivid trousers or enhance the allure of an LBD. The pronounced broad shoulder design, reminiscent of the ’80s fashion era, has undeniably reemerged on the grand stages of high fashion. Admittedly, Serena didn’t often stray from her customary dress ensembles, yet her occasional departures left an indelible mark each time, leaving no room for doubt.
8. Blair’s Timeless Polka-Dot Elegance
In her signature style, Blair maintained an air of timeless sophistication through her choice of dresses, exemplified by this polka-dot creation. (Interestingly, shoes seem to be an optional accessory here?) This ensemble seamlessly transcended the Upper East Side fashion scene of the early 2000s, and its midi length would be equally stunning no matter your location during the spring-summer of 2023 (assuming we can venture out anywhere)—truly a testament to its enduring allure.
9. Serena’s Alluring Lace Details
A jumpsuit featuring a daringly deep neckline and adorned with delicate lace detailing might not be our first choice for a Thanksgiving dinner ensemble. However, when you possess the van der Woodsen panache, why not defy expectations? In the real world, you might reserve this attire for a sophisticated cocktail soirée or an upscale wedding. And, it’s quite the revelation that our very own Serena was the original inspiration behind Fleabag’s iconic appearance, isn’t it?
10. Timeless Elegance: Blair’s Party Perfection
In the sixth season, Blair seamlessly fused two of our favorite elements: eye-catching statement earrings and a twirl-worthy party dress. Those metallic pumps certainly add to the allure… if only strolling in them were a viable option. Can you imagine envisioning this complete ensemble on today’s Kate Middleton during a regal event? Though, it’s quite possible she’d opt for more functional footwear without sacrificing an ounce of style.
Throughout Gossip Girl, fashion aficionados were treated to a captivating parade of ensembles worn by the likes of Blair Waldorf, Serena van der Woodsen, and Jenny Humphrey. Blair’s regal combination of tailored coats and sophisticated headbands echoed timeless elegance. Serena’s free-spirited dresses, often paired with bohemian jewelry, exuded an effortless allure. Jenny’s rebellious transformation from Brooklynite to haute couture was marked by edgy layers and punk-inspired accessories. Amid the whirlwind of trends, here are a few iconic outfits that would seamlessly integrate into today’s fashion landscape, a testament to the show’s lasting style influence.
