For a long time, the headband had a bit of a branding issue. Mention the word, and most of us were instantly transported back to primary school photos, with stretchy cotton bands, awkward fringes, and that unmistakable sense of trying a little too hard to look put together.
Then came its second life. It became inseparable from Blair Waldorf and her hyper–curated Upper East Side world, acting as a literal protagonist in Gossip Girl, where it doubled as a glossy shorthand for status and old–money power.
But in 2026, the accessory was freed from the halls of Constance Billard and folded back into the fashion lexicon. Much of that shift traces back to the renewed obsession with Carolyn Bessette–Kennedy, fuelled by Hulu’s Love Story, which revisits her life with John F. Kennedy Jr. The series has reignited interest in a stripped–back, monochrome wardrobe, pushing that ’90s blueprint back to the top of our feeds.
Amid the frenzy for her precision–tailored skirts and elusive oval sunglasses, the headband stands out as one of the season’s most convincing accessories. On the Spring/Summer 2026 runways, designers like Carolina Herrera and Simone Rocha sent models out with them, styled with restraint in line with the season’s tone.
The aesthetic draws from CBK’s minimalist, understated approach. She frequently wore a simple plastic tortoiseshell headband, a refined detail that complemented her sleek wardrobe.
Fittingly, she sourced them from C.O. Bigelow in Greenwich Village, widely known as America’s oldest apothecary. It was here that she picked up her everyday essentials, including the now much–referenced hair accessory. That same piece now offers an alternative to the cool–girl slick–back and works just as well day to day.
And if you’re looking for the exact version, you already know where to find it. There’s a growing sense of urgency around it now, with shoppers flocking to pharmacy counters in search of that same unassuming accessory once worn by the late style icon. It’s a testament to how enduring her influence remains.
You see it in the way it’s worn now. It’s no longer about placing it perfectly. Rather than meticulously smoothing every strand, the modern approach is deliberately relaxed. Let hair fall naturally or leave a few loose pieces at the front, and the effect feels more akin to throwing on a pair of sunglasses than styling a formal accessory.
The it–girl roster has already claimed it. Madelyn Cline, Olivia Rodrigo, Elle Fanning, Bella Hadid, and Kendall Jenner have all adopted the headband both on and off duty. It balances proportions while introducing a subtle focal point. A textured band adds depth to an all–neutral look, while a slim silhouette brings instant structure when hair feels flat.
It all comes down to a few key styling techniques. First, the ear tuck. Resist the urge to pull everything straight back. Let your hair fall naturally, tucking the front sections behind your ears before positioning the headband to soften the overall effect. Next, the middle part peek. Keep a hint of a centre part visible at the hairline before placing the band, creating a geometric element that feels ’90s runway. Finally, texture contrast. Play with opposites: a sleek plastic band works best against air–dried, undone texture, while a soft fabric band provides a refined counterpoint to smoother, straighter hair.
