90s Nostalgia

With the launch of Love Story, nostalgia for the 90s has reached a new high. As audiences swoon over the retelling of Carolyn Bessette-Kennedy and John F. Kennedy Jr.’s romance, it is not only the love story that has captivated viewers, but the beauty codes of the era too. In particular, Bessette-Kennedy’s chic, understated approach to hair has resurfaced as a blueprint for modern elegance. From tortoiseshell headbands to perfectly imperfect waves, these are the ’90s hair trends returning to favour—and how to wear them now.

Sarah Pidgeon as Carolyn Bessette-Kennedy in Love Story

From sleek tortoiseshell headbands to perfectly imperfect waves, revisit Carolyn Bessette-Kennedy’s most iconic ’90s hairstyles and why they feel so relevant in 2026.

The Headband

If there is one accessory synonymous with Carolyn Bessette-Kennedy, it is the tortoiseshell headband. In the 90s, she made the humble hairband feel impossibly refined, transforming it from a schoolgirl staple into a marker of quiet luxury. Her preferred style—a thick, French-made acetate band by Charles Wahba—was reportedly sourced from Manhattan’s beloved apothecary C.O. Bigelow, and has since become the subject of renewed fascination.

Bessette-Kennedy wore hers with long, straight blonde hair left loose, with a sleek low ponytail, or with a neat bun positioned at the nape of the neck. The effect was effortless but intentional—a subtle frame for the face that complemented her streamlined wardrobe of slip dresses, sharp tailoring and minimalist coats.

Messy, Chic Waves

Carolyn’s hair was never rigid or overly styled. Instead, her natural texture—soft, slightly tousled and subtly sexy—became part of her signature. The beauty of her waves lay in their imperfection. They looked lived-in, as though shaped by the day rather than by heated tools. It is rumoured that she would twist damp hair into a bun during her commute, releasing it upon arrival for that undone bend. Whether apocryphal or not, the method perfectly encapsulates her low-effort philosophy.

If you too weren’t blessed with her chic wave pattern, to recreate this look we’d start with second-day hair for added grip. Using a medium-barrel tong, loosely wrap random sections, alternating directions and leaving some strands untouched. The key is inconsistency — some pieces straighter, others softly waved. Keep the ends relatively straight for that elongated silhouette. Finish with a light texturising spray, lifting at the roots for volume and gently roughing up the mid-lengths. The result should feel airy, not coiffed. Imperfection is the point.

The Head Scarf

For off-duty moments in early 90s New York, Bessette-Kennedy occasionally reached for a silk square scarf, tied bandana-style over her hair. Worn with dark sunglasses and minimalist tailoring, it struck a balance between European insouciance and downtown cool. Today, influencers and heritage houses alike have revived the silk headscarf, folding a square diagonally and tying it over the crown, tucking the centre corner beneath.

Even locally, brands such as Whimsigirl have reinterpreted the concept with modern, culturally rooted designs. Their linen headpiece featuring delicate sulam goyang detailing and a curved hood silhouette offers a contemporary take, blending tradition with minimalist styling—proof that the spirit of the ’90s can be adapted thoughtfully for today.