How to Wear a Headband Like Carolyn Bessette-Kennedy
With the release of Ryan Murphy’s hotly anticipated Love Story—chronicling the relationship between Carolyn Bessette and John F. Kennedy Jr.—Google searches related to “how to wear a headband” have reached fever pitch.
In the 1990s Carolyn Bessette redefined American glamour, fast becoming the poster girl for pared-back, quiet luxury. Twenty-five years after her death, she remains the ultimate fashion icon, constantly referenced for how effortlessly she styled a slip dress, wore the perfect cut of white shirt, coolly fashioned a vintage leopard-print coat.
But there’s one timeless commodity Bessette made her MO: the headband (specifically a tortoiseshell). And it’s now become the It girl’s hottest fashion accessory for spring 2026.
It’s also worth noting that there’s a particular way to style a headband that keeps it looking modern rather than school girl or too preppy, à la Blair Waldorf. Here’s everything you need to know about how to wear a headband for effortless style.
How Carolyn Bessette wore a headband
Carolyn Bessette delivered a master class 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 purchased her go-to headbands—a wide tortoiseshell and a thinner version—at Manhattan 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.”
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.
