Heavy is the head that wears the queen of the Upper East Side’s favorite hair accessory. While Constance Billard may have a new ruling class who thinks that headbands are passé, I — and I suspect many others who’re reminiscing about the OG Gossip Girl series — will always hold a special place in my heart (and on my head) for them.
Of the many things to love about Blair Waldorf, her unparalleled headband game takes the top spot. She single-handedly spearheaded a headband renaissance (ugh, to yield such power), giving everyone a million reasons to fall in love with the hair accessory all over again. Leighton Meester’s iconic portrayal of the Queen Bee proved that headgear could even be sexy. And some her of greatest hits look like literal pieces of art.
Before you dive into the reboot, take a scroll through memory lane just to remind yourself why Blair was — and forever will be — the reigning style queen. Full disclosure: All her looks were so amazing that picking favorites was what I’d imagine picking a favorite child would be like. But for the sake of journalism, it had to be done.
Below, a definitive ranking of 10 of Miss Blair Cornelia Waldorf’s most memorable headband moments on Gossip Girl.
#10 Black Roses
The first time Blair graced people’s TV screens, it was love at first headband. The black hair accessory had big ribbon rose decals and slicked back her long curls. Elegant, glamorous, and absurdly chic, this is when Blair Waldorf and headband pretty much became synonymous.
#9 Hamptons Casual
This silk-scarf-turned-headband looked luxurious yet carefree — which made it the perfect hair accessory for an unexpected run-in with an ex in the Hamptons.
#8 Preppy Plaid
Does the mere sight of plaid conjure up bad memories from your Catholic school days or is it just me? Pardon my projection, but this plaid headband might make you rethink any personal distaste for the print. Blair always knew how to add the perfect touch of personal style to an otherwise boring uniform.
#7 Seductive Ribbon
Can a headband be sexy? Absolutely. While drinking a martini and flirting with bad-boy Carter Baizen, Blair demonstrated that the classiest hair accessory can easily be alluring.
#6 Summer White
This headband (another Hamptons classic) was worn at a pivotal time in the Chuck and Blair saga. “Three words. Eight letters. Say it. I’m yours.” It’s arguably her most iconic line (#IYKYK) and Chuck fumbling the response still ranks high in WTF Gossip Girl moments.
#5 Royal Jewels
Oh, Prince Louis. Even if that marriage went south real quick and didn’t ultimately last very long, Blair was a legitimate princess and had the bejeweled accessories to match.
#4 Bold Bows
This is when she shattered the notion that bows were only for the holiday season or girls below the age of 10. Blair used this moment to prove that huge bows are, in fact, high fashion, wearing a bright red headband that was sophisticated and bold.
#3 Flower Power
If there was a headband that could steal the spotlight from a bride on her wedding day, this would be it. Adorned with flowers, a fuchsia headband was the perfect match to B’s floral mini dress.
#2 Princess Diaries
While this tiara is — gasp — cubic zirconia, it’s one of Blair’s most important headpieces. It’s symbolic of what should’ve really been endgame: Blair and Dan. Their chemistry was undeniable, their witty banter was just goals, and they had the most in common, IMO.
#1 Wedding Crystals
Setting my personal distaste for Chuck aside (the man is toxic as hell), Blair looked flawless at her second wedding. To match the embellished long-sleeve Elie Saab gown, her hair is styled in a low chignon and adorned with a crystal leaf headband. It was classy, elegant, poised — just how people will always remember the reigning queen of the Upper East Side.
