Leighton Meester Is Giving Vintage Blair Waldorf at Milan Fashion Week

Hey Upper East Siders, we have all the details on a super rare Blair Waldorf sighting in Italy’s fashion capital this week — well, maybe it wasn’t exactly Blair who we saw. Turns out, it was Leighton Meester who looked the part of her iconic Gossip Girl character while wearing an outfit during Milan Fashion Week that a grown-up Blair would have easily chosen.

RELATED: The Meaningful History of Headbands

To attend the “A Legs Celebration” event hosted by Italian hosiery brand, Calzedonia, Meester wore a pale grey halter mini-dress by Camila and Marc. She paired the look with black sheer tights from Calzedonia, one of Blair’s signature accessories throughout Gossip Girl’s six-season run, along with glossy Manolo Blahnik pumps. And, in true fashion forward style, she followed this season’s hottest colour trend by adding a cherry red handbag from By Far that complemented her matching red manicure.

 

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Meester kept the rest of her look simple by opting only for a pair of small stud earrings and no other jewellery. And, with her brunette hair styled in a retro updo, she ultimately stood apart from her memorable character with one major sartorial choice — she skipped Blair’s favourite accessory, a statement headband.

Despite leaving her headband at home for the evening, the pairing of black tights with a mini-dress, plus Meester’s very Blair bangs, gave the outfit a preppy vibe that we can’t help but link to Ms. Waldorf — which Gossip Girl fans also picked up on straight away.

“Tights just like classic Queen B would do!!” exclaimed one reply on X. “If you don’t recognize Blair in this picture you live in a cave,” shared another commenter on Instagram.

For a classic outfit combination of tights paired with a high hemline to cause so much commotion proves the mark of a true style icon — and considering that Meester hasn’t been seen in character as Blair for over 11 years since the show went off the air in 2012, that is quite the accomplishment.

But, between the Gossip Girl reboot of 2021, which introduced a whole new generation to the original Upper East Side crew, and Blair’s style consistently going viral on TikTok to this day, it’s not surprising that fans were so quick to point out Meester’s resemblance to Waldorf on the red carpet.

Throughout the original series’ run, Blair, a privileged Upper East Side teenager with a fashion designer mother, was known for her polished, often glamorous, style that made her appear well beyond her years. This was achieved with a variety of designer looks that the character sported for her everyday activities — think: shopping in Paris, hanging out on the steps of the MET before class, having lunch at the Plaza Hotel, etc. And even went she wasn’t wearing designer, Blair still made everything from her pyjamas to her school uniform look expensive, a feat that both Meester’s performance and the addition of a signature headband both helped accomplish.

The character particularly favoured traditionally preppy accessories, such as tights (which she seemingly owned in every possible colour) and ballet flats, not to mention her extensive headband collection, which have since come back into style thanks in part to the quiet luxury aesthetic.

By committing Blair to these carefully curated fashion choices for the entire series, the show’s costume designer, Eric Daman, ensured that the character, and consequently Meester, would forever be known for her signature glamorously preppy style — one that has spawned countless recreations and subsequent trends on social media years after the show’s finale.

The Blair Waldorf style impact is so strong that it follows Meester even when she isn’t dressed like the character in the slightest, which just happened again during this Milan Fashion Week. Despite looking nothing like Blair while casually strolling around the Italian city in an olive green dress, red strappy sandals, and sunglasses, Meester went viral in a TikTok that highlighted her off-duty look with the unmistakable Gossip Girl theme song playing in the background.

We can’t help but wonder if Meester will grace us with another stellar look in Milan before the city’s fashion week festivities are through. That’s a secret that only time will tell. XOXO…

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