With the release of Ryan Murphy’s hotly anticipated American Love Story, chronicling the relationship between Carolyn Bessette and John F Kennedy Jr, Google search around “how to wear a headband” has reached fever pitch.
In the ‘90s, Carolyn Bessette redefined American glamour, fast becoming the poster girl for pared-back, quiet luxury. 25 years after her death, she remains the ultimate fashion icon, whether you’re looking to channel how effortlessly she styled a slip dress, wore the perfect cut of white shirt or coolly fashioned a vintage leopard print coat.
But there’s one timeless commodity she made her MO: the hairband, specifically a tortoiseshell headband, and it’s now become the It girl’s hottest fashion accessory for Spring 2026.
But it’s also worth noting that there’s a particular knack to styling a headband to keep it looking modern rather than school girl or too preppy like Blair Waldorf. Here’s everything you need to know about how to wear a headband for effortless style…
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How Carolyn Bessette wore a headband
Carolyn Bessette delivered a masterclass in how versatile a headband can be, styling her long blonde hair straight and loose, in a sleek low ponytail or gathered in a nape-skimming bun. She typically purchased her hairbands – a wide tortoiseshell and a thinner version – in Manhattan’s pharmacy C.O. Bigelow.
“Carolyn’s look is so iconic because it’s timeless, simple and chic,” says hairstylist Issey Cooke from Larry King’s London salon. “Today we see these types of headbands a lot as they are still modern but have a vintage feel. It can be styled so effortlessly with your hair down or up and as a classic day to night accessory.”
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How to style your hair with a hairband
If you’re wearing your hair down:
“For something simple and effortless, a smooth, straight blow-dry works beautifully,” says Issey. “It has a subtle ’90s feel – think Cher in Clueless.” Prep wet hair with a heat protectant and smoothing cream, and rough dry. When hair is 90% dry, hold the hair dryer a few inches above a paddle brush and gently pull the brush to the ends, smoothing down the flyaways as you go.