Here at RUSSH, our affinity for Carolyn Bessette Kennedy's style is well documented. While many of tried to emulate her signature brand of chic simplicity, decades on, few have managed to match the original. And thanks to Ryan Murphy's American Love Story, Bessette Kennedy's sartorial prowess has been catapulted back into our collective consciousness. As we devour each episode (and if you haven't what are you doing?), our social media feeds are simultaneously flooded with a new generation of women attempting to reproduce some of Bessette Kennedy's most iconic looks, from perfectly cut boot-leg jeans, to expertly-placed tortoiseshell headbands.

Of course, beyond her style instincts, working as a publicist at Calvin Klein means Bessette Kennedy has a leg up on most of our wardrobes already. As American Love Story demonstrates, Bessette Kennedy was something of a rising star at Calvin Klein, graduating from sales associate to the director of publicity in a matter of years, with decisions like making Kate Moss the face of a campaign among her most significant contributions to the brand. And as she ascended the ranks, she did so in an enviable wardrobe of pencil skirts, slip dresses, and tailoring so good it practically makes your mouth water.

Fast forward three decades, and the staying power of this understated way of dressing has never been more pertinent. It might be 2026, yes, but our desire to dress like a 20-something-year-old publicist running through New York in the nineties has never been stronger. So, how does one recreate Carolyn Bessette Kennedy's style, all these years later? Our guide to the chic pieces we think she'd be shopping in 2026, below.

A casual midi-skirt look

BOTTEGA VENETA Midi Skirt

LOEFFLER RANDALL Goldy Boots

CAMILLA AND MARC Leona Knit V Neck Sweater

FREJA New York Caroline Bag

The perfect winter denim ensemble

M.N.G Long Combined Coat

UNIQLO 100% Australian Merino Ribbed Turtleneck Sweater

REFORMATION Sharon Stretch Mid Rise Bootcut Jeans

CHURCH'S Onyx perforated leather loafers

SOPHIE BUHAI Brown Thin Bessette Headband

Eternally chic dog-walking attire

ST AGNI Canvas 90s Low Rise Jeans

HARRIS TAPPER Long Sleeve Orwell Polo in Silk Wool

THE ROW Dune leather flip flops

SAINT LAURENT Erin oval-frame acetate sunglasses

A summer-in-the-city slip dress

MATTEAU Square Slip Dress 

GENTLE MONSTER Cuscus 01

ALIAS MAE Ivana Loafers

(Another) midi skirt moment

BALLY Cotton-corduroy midi skirt

FLORE FLORE Steffi ribbed organic cotton-jersey T-shirt

THE ROW Penelope Mule