The first time I paid really close attention to Carolyn Bessette-Kennedy’s accessories was when I decided to put together a vintage collection inspired by the exact shoes and handbags she wore. One piece in particular stood out: a Cartier Tank that she was pictured wearing while entering her Tribeca apartment. For years, the watch was rumored to have been a gift from her mother-in-law, Jackie Kennedy. To this day, there has been lingering mystery around the exact model Bessette-Kennedy wore. Photographed in it only a handful of times, the watch’s origin story is the stuff of lore, and one of the many pieces of hers that would go on to be closely examined.
It’s her approach to accessories that reveal the most to me. Of course, we’re all familiar with Bessette-Kennedy’s famous Charles Wahba headband and Selima Optique sunglasses, but many of the finishing touches that shaped her style were quieter—from her shoes to her jewelry, and the bags she wore day in and out. And in a time when constant rotation has become the norm, there’s something grounding about seeing a woman repeat the same shoes, bags, and jewelry until they become second nature. Her accessories, much like her clothing, were tight in number but deliberate in choice—subtle details that gained meaning through repetition—much of which is routinely passed over today in comparison to her clothing. To understand Carolyn Bessette-Kennedy’s style fully, let’s take a closer look at the accessories she returned to again and again.
The Headband and Sunglasses
Two of Carolyn Bessette-Kennedy’s most enduring signatures appear here, worn exactly as she intended them to be: functional, repeated, and quietly distinctive. The Charles Wahba headband and Selima Optique Aldo sunglasses were never styled as statements, yet over time they became inseparable from her image. Decades later, they still feel current.
The Shoes
Throughout the 1990s, Carolyn’s footwear choices were remarkably focused, and she rotated almost exclusively between two designers: Prada for day, Manolo Blahnik for night. Practical boots, worn-in loafers, and sensible kitten heels from Prada grounded her daytime looks, switching to Manolos when the occasion called for something more formal—galas, dinners, and a custom pair for wedding day. She shopped for her shoes herself at Manolo Blahnik’s former New York flagship on West 54th Street, reinforcing how central the brand was to her wardrobe.
I’ve spent years studying her shoes, and what still stands out is how intentional her choices were: The styles she wore in the ’90s remain some of the hardest to track down on the secondhand market today, not because they were particularly trendy, but because they were well-worn—often past the point of resale. What always stood out to me, and what those closest to her consistently confirm, is that Carolyn had an incredible eye, not per se for spotting trends, but for her patient discernment in choosing those pieces she could live in.
The Pradas
I love this image because it shows Carolyn’s style at her most pared back. She wasn’t at a gala, trying to move through a horde of photographers. It’s a rare unguarded moment of Carolyn Bessette‑Kennedy, photographed at Teterboro Airport with her family. Dressed simply in jeans, an oversized knit, and sneakers, removed from spectacle or occasion, this is an outfit that still feels incredibly relevant today. Images of Carolyn in sneakers are few, but the handful that exist remind us how consistently she dressed for comfort and function.
The Jewelry
Bessette-Kennedy’s approach to jewelry was perhaps the most considered portion of her wardrobe. She rarely wore anything overtly decorative in the jewelry space, favoring pieces that felt personal versus flashy. A simple wedding band and a discreet timepiece which she wore with regularity are telling of her overall approach. On the occasions when Bessette-Kennedy did wear something more elevated jewelry, those pieces left a lasting impression. A good example is the intricate leather detail of a Jean Paul Gaultier top (often mistaken for a necklace) which continues to inspire designers today, including Juju Vera, who recently reinterpreted the piece as a pendant. To understand Bessette-Kennedy’s style fully, it’s worth taking a closer look at the jewelry she made her own—quietly, but with lasting impact.
Bessette-Kennedy enters her Tribeca apartment with her dog, Friday. She’s wearing a Cartier Tank that always stood out to me. The watch’s origins have been for years the source of much speculation: where it came from, who bought it, and which model she wore. For me it was never really about the exact style, but rather the way she wore it, not as statement but as part of her daily uniform. It functioned as a true everyday watch, one that feels as relevant now as it did then.
Bessette-Kennedy routinely wore minimal wedding bands—one being a solid gold band and the other a sapphire and diamond pavé band. Simple in form, her rings reflect how deliberately she approached jewelry: few pieces, chosen with care, always worn for meaning rather than display.
The Bags
Carolyn Bessette-Kennedy approached bags with the same consideration that defined the rest of her wardrobe. She owned few, but wore them decisively—pieces chosen for life in the city rather than display. By day, she relied on pieces that could carry the weight of real life-from her worn-in Hermès Birkin to the sleek Prada Spazzolato tote—bags chosen to hold her belongings and move with her through the city. Evening functions called for something smaller and more contained, often pared down to a small clutch or simple wallet.
