Gossip Girl: Blair’s 10 Best Headbands, Ranked

Headbands are back, as evidenced by Amanda Gorman, National Youth Poet Laureate and activist, who wore a red one to recite her poem, “The Hill We Climb,” at President Biden’s inauguration, and again when she chose a pearl band as the first poet to perform at the Super Bowl. Let us not forget, though, that it was Gossip Girl queen bee, Blair Waldorf, who got this statement accessory ball rolling some 14 years ago. And what an array she had: a band for all occasions if you will.

Even though her minions followed her lead, meaning Blair was often imitated, her flair for how to wear the hair adornment could never be duplicated.

10 Wrapped Up In A Bow

She was just the gift that kept on giving, wasn’t she? Blair ruled her world from the steps of The Met and whether she was planning a soiree (for which she made Little J. address the invites) or plotting the demise of a frenemy (then didn’t invite Jenny), Blair dressed for success, yet no ensemble was complete without her signature headgear.

The double-bowed band coordinates with Blair’s lip color, then picks up the red stripe in the Constance Billard school uniform blazer for a subtle match, so the eye follows in one fluid motion.

9 A Simple Strand Of Pearls

Some might wear a simple strand of pearls around their neck and pair it with a little black dress, but standout Blair wore one around her head with a cream and black strapless dress.

Even this chic outfit Blair chose the first time she dated royalty embodied by Marcus, who she met in the Hamptons and whose stepmother was the married neighbor Nate was having the affair with, could not save this season 2 relationship. She would have to wait another day (or season) to become nobility.

8 She Loves Him, She Loves Him Knot

Breakin’ up is hard to do, so you might as well look good doing it. Nate gave Blair the heave-ho when he found out that she struck a deal with his rich and powerful (and scheming) grandfather in order to be a bridesmaid at cousin Tripp’s wedding. (the politician who had an affair with Serena.)

Blair knew the blow-off was only temporary, since she just looked too good in her elegant chiffon dress with high ruffle collar, kicked up to the next level of chic with her brown satin headband accentuated by an ear-covering flower.

7 The Crown Jewels

In the second episode of the final season, it was time to shine for Blair. Following in her mother’s footsteps, the scion begins her career in fashion. What B always lacked in social skills, she made up for in talent and her “dress as I say, and as I do” style.

The new reigning queen of NYC’s 7th Avenue (home of the garment district) needed to straighten her crown and get to work. The headwear she chose was look-at-me pink adorned with jewel-toned baubles that resembled rubies, emeralds, and sapphires.

6 Tied and True

In “Summer, Kind of Wonderful,” Blair and Serena spent the tanning season in the Hamptons, (when Nate had the affair of his married neighbor). The pouty brunette claimed to be showing all the Upper East Side that she was over Chuck Bass.

Although she packed her share of traditional headwear, in the vein of “new Blair, new band” she chose to wrap a blue and purple scarf around her ‘do. It doesn’t exactly match her floral frock or even her straw bag with hot pink accents, but for some reason, it works.

5 Go For The Gold

What do you wear when your guy finally says “I love you,” after returning from traveling throughout Europe where he went on a shopping spree to gather all your favorite things? If you’re Blair Waldorf, you wear a unique, golden nautical-themed rope headband that symbolizes she’d sail the seven seas to be with her man.

It also perfectly coordinates with her gold, brown, and yellow ensemble contrasted by her Kelly green coat. Being who she is, it’s no surprise that after Chuck made his declaration of love, Blair made him say it again, just to be sure.

4 Flower Power

It’s flora to fawn over. In the season 1 finale, it may be Lily’s wedding day, but all eyes are on Blair in her pink and white swirl of a dress, with full frontal flower, and of course, she found a solid pink blossom headband to interweave with her braided ‘do.

No matter how pretty-in-pink Blair looks, there’s a moment when things are more melancholy than rosy. Blair seeks out Serena, who admits that she feels her mother’s heart isn’t in the marriage to Bart, leading Blair to ask if one day either of them will be preparing for her fourth wedding.

3 Showing Off Her Pearly Whites

In her black sequin gown and updo adorned with a contrasting pearly white beaded band, Blair is the belle of the ball — even if the ball is going to get dropped on its head.

The doyenne-in-the-making is determined to save her mother’s fashion house by debuting a non-traditional dress at the upcoming Cotillion, which she wants rebellious Sage to wear. The teen agrees, but only if Blair helps stop the engagement between her dad, Steven, and Serena. But Sage decides Blair can’t be trusted and when it’s her turn to be presented, the 17-year-old throws off the top layer of Blair’s dress just as the large-screen TV plays Dan and Serena’s sex tape.

2 Her Crowning Glory

The blushing bride (for the second time) wore a blue gown embroidered with rhinestones and a diamond laurel wreath band as her headpiece when, in the series finale, she married Chuck Bass in New York’s Central Park (before the NYPD showed up to arrest him).

Nothing could have been more appropriate as far as the headwear was concerned, since the laurel wreath, which traces back to Greek mythology, is a symbol of triumph. In Roman times, it too represented victory. Who was ever more of a tour de force than the Upper East Side’s Blair?

1 Diamonds Are A Girl’s BFF

When does a headband transform into a many-carat tiara? The day Blair married Prince Louis of Monaco. At their wedding, however, a video taken by Georgina of the bride professing her love for Chuck was leaked. Louis and Blair went through with the ceremony, but the groom informed his new wife that going forward their marriage was only for show.

When Blair tried to get a divorce, she realized the dowry her family would owe would ruin them. Ultimately, Chuck came to Blair’s rescue and paid the settlement. It’s good to be queen … of the Upper East Side.