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…
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.”
How to style your hair with a hairband
“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.
“Push the headband into place, leaving a soft, natural front section so the look feels relaxed rather than overly flat or tight,” says Issey.
If you want something more statement, Issey recommends a voluminous '60s-inspired blow-dry for instant glamour. Use a volumising mousse on damp hair and, instead of pulling the brush through your lengths, use it lift the hair up at the root and finish with Velcro rollers. “Position the headband between the front and back sections so it acts as an accessory rather than pulling the hair fully away from the face. Leave a small face-framing section loose at the front.”
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“First you need a tacky base, so I would use the Larry King Flyaway With Me Kit alongside a gloss spray or gel to create the wet look," says Issey. "Simply scrape the hair back and finish the look with the headband.”
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“The minimalism of this look is what makes it look expensive,” says Issey. “When styling a ponytail with a headband, a lower ponytail tends to create the most balanced result. It keeps the hair smooth and allows the headband to sit comfortably without competing with height or a strong parting.”
Apply a primer and then blow-dry the hair smooth. You can also opt for a few passes with a hair straightener to ensure the texture is consistent from roots to ends. Work a styling cream into strands for added shine without stiffness, then gather your hair at the nape of your neck, roughly in line with the tops of your ears, and smooth down any bumps before securing with an elastic.
If you prefer a low bun, simply twist the ponytail and wrap it around the base, securing it with bobby pins and an all-over mist of hairspray. “Once the shape is refined, position the headband so it complements the style and enhances the overall finish,” adds Issey.
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“For a softer, more relaxed finish, try a messy backcombed updo paired with a headband,” says Issey. Begin by roughly measuring how far back your headband will sit to avoid squashing the height at the crown.
“Then section a large diamond shaped area just behind where the headband will sit,” says Issey. “Backcomb this section to build height at the crown, then lightly smooth the surface with a soft bristle brush to keep the volume while maintaining a natural texture. Loosely gather the remaining hair into a soft updo, allowing pieces to fall naturally for a slightly undone feel.”
Finally, place the headband just in front of the backcombed section. “You want the volume to sit behind the headband as this frames the face while highlighting the height and movement through the style,” adds Issey.
The best hairbands to elevate your look:
“The beauty of hairbands is that they work with pretty much every hair type, but if you have thick, coarse hair you might want to find a hair band with a claw or grips on the inner rim to ensure it sits securely," advises Issey.
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For more from Fiona Embleton, GLAMOUR's Associate Beauty Director, follow her on @fiembleton.
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