If you’re anything like me, the sight of a stretchy cotton headband is enough to transport you straight back to primary school. The simple hair accessory – in school colours like bright red or royal blue – was a mainstay in the wardrobes of those of us who grew up in the early 2000s. But of course, the humble headband was doing the rounds long before we were traipsing into the classroom.
In the 1920s, Gatsby-esque head wraps were all the rage, dressed up with drop-waist dresses, sleek bobs, and layers of pearls. Fast-forward a few decades to the 70s, and the humble headband took on a new iteration, in the form of multi-colour wraps tied just above the eyebrow. Then, in the 90s, style icon Carolyn Bessette Kennedy made a case for the headband as the ultimate understated hair accessory. She was a proponent of the Alice band – a flexible, plastic headband that she typically donned in neutral shades like tortoiseshell or black. And in the 2000s, Blair Waldorf made us fall in love with headbands all over again, thanks to her penchant for preppy styles, often jazzed up with bows and pearls.
Now, the headband has re-entered fashion’s lexicon – in a big way. First, there's Ryan Murphy's American Love Story, which has us not only swooning over Carolyn and John's romance, but the fashion of the time — including headbands aplenty. There's also current day it-girls Madelyn Cline, Bella Hadid, Kaia Gerber, Hari Nef, and Kendall Jenner (to name a few), who have all sported the simple accessory in recent months.
And if their stylings tell us anything it's that, when it comes to headbands in 2026, less is more. In fact, like many of the trends we’re wearing today, the headband du jour takes its cues from the effortless cool of the ‘90s. Think: simple neutral colourways, in unfussy silhouettes. It's also a lazy girl's hairstyling dream. Forgot painstakingly straightening pesky flyways: a headband is the ultimate throw-on-and-go hair accessory.
Below, start planning your spring looks with five on-trend headbands to shop now.
Sophie Buhai Brown Thin Bessette Headband
The Bahay Headband
Mode Mischief Grand Headband
Lele Sadoughi Brigitte Headband
Sophie Buhai Bessette acetate headband
TOTEME Beige Cashmere Headband
J Crew Tortoise Headband
Toothed Hair Hoop Headbands
Featured products are selected editorially. Our opinions are our own. Occasionally, we may receive a standard affiliate partner fee if you make a purchase using the links we feature.
