IN THIS YEAR’S REBOOT of “Gossip Girl,” the latest Upper East Side queen bees try to knock the headband off its prissy perch. Zoya, an underdog character new to Manhattan, shows up at the fictional Constance Billard School wearing a knotted scarf around her locks. “She has a headband on,” scoffs the trendy upperclassman Monet. The implication is that headbands—as worn by Blair Waldorf in the original series that debuted in 2007—are over.

Not so fast, “Gossip Girl.” The reboot’s creative team might be eager to cut ties with the idealized Edith Wharton-inflected world of the show’s first incarnation, but they’re out of step with the zeitgeist. While a too-literal bow-band atop a preppy ensemble is certainly a relic, the statement headband is actually more pervasive than ever.

Was there a more indelible fashion moment in 2021 than Amanda Gorman’s cherry-red Prada headband at President Biden’s inauguration? Second Daughter Ella Emhoff, known for her avant-garde style, also wore a black Loeffler Randall headband to the event. For everyone from celebrities like Mindy Kaling to—most likely—Jill from your office, the headband has been a fixture on Zoom screens over the past year. Versions both affordable (Etsy!) and designer (Simone Rocha!) are selling like hotcakes. For an era awash in screen-filtered uncertainty, the headband takes a firm style stance.

Amanda Gorman wore a distinctive Prada headband for her 2021 inauguration performance.

Photo: Getty Images

The headband’s history is slightly schizophrenic. It’s meandered from 1920s flapper insouciance to ’50s glamour to a staid preppiness in the early ’90s, when Hillary Clinton’s trusty headband was widely criticized. In her 2003 book “Living History,” she wrote that even friends told her “the headband had to go.” It took the first “Gossip Girl,” with its winky dusting-off of old New York tropes, to rejuvenate it. Brands like Jennifer Behr—still a headband stalwart—reported booms in sales following appearances on the show. In 2008, whether coincidentally or not, rebellious socialites like Arden Wohl and Peaches Geldof took to wearing headbands across their heads like tiaras (as Princess Diana had done presciently in 1985 with an heirloom emerald necklace).

Hillary Clinton, wearing a headband at the White House in 1997, later ditched the style.

Photo: Getty Images

The headband has held fast since then, although today’s versions are not placid bourgeois tortoise-shell bands. They’re often high, puffy, and upholstered in bright or patterned fabrics. Simone Rocha, a U.K. designer who has made headbands a signature since 2014, pioneered a kind of jeweled crown-like style that has filtered down to the masses. Hill House Home, the populist purveyor of the viral Nap Dress, has leaned into this tiara-ish headband style, with a new “back-to-school” collection of them set to drop next week. Nell Diamond, the brand’s CEO and a headband devotee, called them “a fun way to take your look to another level.”

Elizabeth Holmes, the author of “HRH: So Many Thoughts on Royal Style” (and a former WSJ reporter), observed that this headband moment was about individualism rather than conformity. She explained that when you wear one, “You’re standing out and making a statement.” The first headband of this ilk she recalls noticing is Kate Middleton’s rather enormous white Jane Taylor piece, worn to Prince Louis’s christening in 2018.

The designer Simone Rocha often features headbands in her collections like this pearl-encrusted one from 2020.

Photo: Simone Rocha

Lisa Aiken, the newly minted fashion and lifestyle director of Neiman Marcus, also sees the headband as part of a move toward stand-out flair. She reports that in 2020, Neiman’s headband sales spiked 950% from the previous year. “The clients are 100% behind the headband,” she said. And Ms. Aiken plans to continue the retailer’s investment in the piece. Like Ms. Holmes, she feels, “It’s less about fitting in and more about an individualist approach.” For her, that approach means styling it with “a carefree attitude where it’s not going to come off too prim.” For fall she plans to wear a “fat, flattened” black Jennifer Behr headband with a casual white T-shirt and straight jeans.

Los Angeles designer Autumn Adeigbo offers celebrity-approved headbands and matching outfits.

Photo: Meg Urbani

Autumn Adeigbo, a Los Angeles designer, has made headbands a core part of her fledgling business. Although she only started making them—by hand—in early 2019, her designs have since appeared on stars like Kristin Bell, Kerry Washington, Ms. Gorman and Ms. Kaling. From Q1 2020 to Q1 2021, sales of her headbands have grown by 300%. They’re now made in a woman-owned factory in India. In Ms. Adeigbo’s lookbooks, headbands are often shown paired with dresses made of matching globally sourced textiles. She said, “I feel like there’s a lot more variety and design consciousness put into headbands. Today we’re thinking of all the different kinds of women who might gravitate towards them.”

Joyce Lee, the founder of the brand Her Place, is also trying to reach an unconventional headband wearer with her long, satin, multi-use ribbons. They can be knotted around the hair, headband-style, or tied around a ponytail. The twist is, these dainty ribbons can be used in the bedroom as well. Ms. Lee explained, “During the day, she’s sweet with this headband, and then at night she takes it off and it becomes this bondage thing.” She explained, “I like the duality of it. You can’t pinpoint a woman just by looking at her.”

So if headbands are more in than ever, why did “Gossip Girl” reject them so soundly, beyond a desire to ditch the iconography of the show’s initial run? The new show is certainly trying to position its characters as iconoclastic, wearing such cutting-edge designers as Bode and Wales Bonner. Whereas headbands are now so widespread that true trendsetters will be looking elsewhere—to head scarfs, for example, as shown by designers like Hedi Slimane at Celine. Ms. Aiken mused that for high schoolers the trend cycle moves almost too quickly to keep up—”things have literally a monthly lifespan,” she said.

And it may have just been good old-fashioned Darwinist social triage in action. “Them making fun of a headband is a really easy swipe,” said Ms. Holmes. She continued, “Because the headband so often stood for prim and proper and preppy, to diss someone’s headband is a really easy dismissal of a person’s style.” Judging by sales figures though, the headband might survive the mean girls.

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