Hey Upper East Siders, CR is uncovering the secrets of Constance queen and tastemaker extraordinaire Blair Waldorf and you won’t want to miss it. The brunette graced the screens of the CW’s hit show from 2007 – 2012 and while you may not be Queen B, if there’s anything we know about Blair it’s that she’s never objected to followers trying to emulate her perfectly primped style. Preferring to pursue high society over Serena Van Der Woodsen’s frequent appearances on Page Six, Blair Waldorf went on to marry a prince, divorce said prince, intern at a fashion magazine, and follow her fashion designer mother’s footsteps with a line of clothing inspired by her prep school days. An OG 2000’s influencer, anyone?
While the Y2K fashion of the original Gossip Girl series may be circling back around, we wanted to step back from the metallic pumps and slouchy bags to muse about what Blair Waldorf would’ve worn in 2021. HBO’s Gossip Girl reboot, premiering on July 9, promises an edgier, modernized wardrobe for their gang of rich Upper East Side teens but the original Blair Waldorf is less edge and more Audrey — a key component to her personal style that she would’ve surely carried with her almost a decade later. It’s a heady mix of old money, Hollywood elegance, and florals for weekends spent in the Hamptons, inspired by the classic wardrobes of Audrey Hepburn and other Golden Age starlets. Here’s what Blair would’ve stocked her present-day closet with — and yes, plenty of bows are still involved.
Alice & Olivia
Stacey Bendet’s Fall 2021 collection for Alice + Olivia was directly inspired by Gossip Girl and the elite teens of New York City. Bendet worked directly with Eric Daman, the man behind the 2007 and 2021 versions of Gossip Girl as well as the costume designer for other notable projects such as The Carrie Diaries. Every classic Upper East Side motif is present, from dainty pearl headbands to uber-preppy prints in shocking shades of black, red, and white. Tweeds abound, plaid is key, and we think that Blair’s darker side would’ve loved the layering of sheer black lace under pinafore-style necklines. Blair tended towards higher collars and just the right amount of frill, which is something that Bendet nailed in her collection, and she loved a slip dress as well.
If there’s one thing that Blair loves (other than Chuck Bass, and of course, herself) it’s a good coat. 2021 Blair was fond of a classic trench and definitely spent time on Fifth Avenue buying more than a few for conquering chilly New York City winters. Max Mara‘s coats would provide her wardrobe with practicality and timelessness while leaving wiggle room for updating some silhouettes and playing with the occasional statement color that Blair loves — we wouldn’t be surprised if she had matching fascinator hats to go with each one.
Blair is always tapping into feminine energy when she gets dressed, and Chloé’s midi dresses are a more grown-up take on Blair’s polished style from her Yale days. She’d love the bolder florals for summering in the Hamptons, and the female-led brand boasts pieces with just the right amount of balance of sharpness and sweetness that would be perfect for Blair. Though Serena Van Der Woodsen is the more bohemian, free spirit of the duo, Blair would consider Chloé’s looser shapes to be a chic step up from the younger silhouettes she wears early on in the show and would more likely style even their most bohemian pieces in a preppy way.
As Blair Waldorf grew up and progressed throughout her career as a designer, we like to think that she’d begin to develop a taste for the romantic, all-American, tailored pieces that Ralph Lauren offers. It’s slightly more subtle than some of Blair’s typical statement choices but she’s always had an affinity for the clean lines of professional clothing. 2021 Blair might reach for a gorgeous sheath dress for a meeting, or attend an evening function at an art gallery in one of Ralph Lauren’s more formal pieces. Let’s not forget their menswear either; we can’t imagine Blair and Chuck not entertaining the idea of a matching power-couple ensemble.
Blair was never one to shy away from a whimsical piece, as evidenced by her bubble skirt dress from Moschino that’s dotted with cherries and apples. With the fruit motif on the rise again, in 2021 Blair would fully lean into experimental, statement-making fashion with something like this Oscar De La Renta dress worn by Meghan Markle, a fresher take on her previous maximalist tendencies when it came to print mixing. Playful fruit prints may even be the new florals, especially if Queen B declares that they are — they’re good enough to eat, if we do say so ourselves.
Puffy Sleeves and Oversized Collars
Preppy-chic Blair Waldorf loved a collar back in the late 2000s, so the oversized statement collar trend would’ve been right up her alley. Pair that with the voluminous princess sleeve of her dreams (minus the scheming prince husband that she had to later divorce) and you’ve got a romantic, sartorially-sharp combination that Blair would still be drawn to a decade later. This Patou piece might be a little out of Blair’s comfort zone in terms of silhouette, but the sartorial tastemaker has never been opposed to the idea of taking up space.