As someone who regrets some of her fashion choices from as recently as a year ago, I’m genuinely in awe of how well Carolyn Besette Kennedy’s style has aged. If our recent obsession with Love Story: John F. Kennedy Jr. and Carolyn Bessette is any proof, her understated outfits somehow look *just* as chic 30 years later. Lucky for us, they’re also pretty simple to recreate.
The late fashion publicist had a discerning eye for avant-garde designers like Yohji and Ann Demeulemeester—as well as heritage brands like Prada and Hermes—but there’s no need to splurge on luxury labels to embody her timeless style. Ahead, I’ve identified six fashion essentials you’ll need to channel CBK’s oh-so-effortless aesthetic. From tortoiseshell headbands to trusty Levi’s jeans, these pieces are bound to become staples in your wardrobe, too.
The Understated Accessories
Famously, CBK almost never wore jewelry (outside of that stunning diamond and sapphire engagement band), but that's not to say she skipped accessories altogether. Instead, she was often seen sporting acetate headbands from NYC-based apothecary C.O. Bigelow and oval-shaped sunnies—specifically, the Aldo style from Selima Optique. Her exact pieces are on backorder right now, but I spotted near-identical styles at Amazon and Nordstrom.
Ray-Ban Oval Sunglasses
Camila French Headband
Le Specs Outta Love Sunglasses
Emi Jay Starlet Headband
The Belted Coat
I can personally attest that New York City winters are brutal, yet Carolyn braved the cold in style with an assortment of fabulous coats. Her outerwear collection ranged from bold red plaid to classic camel and black, but they all had one thing in common: a belted waistline. This fur-accented coat is a glamorous pick for nights out, while this plaid belted trench transitions easily from winter to spring.
Mid Trench Coat
Wolf & Badger Double Breasted Checks Coat
MANGO Manteco Belted Longline Trench Coat
Damson Madder Anja Reversible Trench Coat
Aritzia The Finch Trench Coat
The Black Tote Bag
Ever the practical style icon, Carolyn favored bags that could actually hold everything she needed for the day (no micro-mini purses to be found!). She often donned a rotating assortment of black leather totes from Hermes and Prada, and you still shop one of her staples, the Prada 1995 Re-Edition Bag. I've also included some more, ahem, affordable alternatives from Quince and JW Pei, in case you don't have an extra 4 grand lying around!
JW PEI Hana Medium Tote Bag
Prada Re-Edition 1995 Leather Handbag
Quince Italian Leather Triple Compartment Work Tote
Coach Soft Empire Carryall Bag 28
Freja Linnea Tote Black
The Bootcut Jean
Levi's jeans truly never go out of style, so it's no surprise that they were a mainstay in Carolyn's wardrobe, too. She often borrowed from the boys and sported the 517 bootcut jeans in a medium wash, which you can still shop today. Contemporary cuts like the 725s, the Wedgie Bootcut, and the Superlow Boot jeans offer a similar silhouette, too—and if you're looking for more curve accommodation, our editors adore Abercrombie's Curve love Mid-Rise Bootcut Jean.
Abercrombie & Fitch Curve Love Mid Rise Bootcut Jean
The Contemporary LBD
It only makes sense that CBK was partial to an LBD, considering she was a publicist for Calvin Klein. While her collection of structured black column dresses and slinky slips might seem simple to the untrained eye, she had a love for architectural silhouettes and asymmetrical details. You can channel her effortless energy with similar looks from Aritzia and Norma Kamali.
Aritzia Original Contour Enrapture Maxi Tube Dress
The Drop Ana Slip Dress
Toccin Chelsea Sleeveless Midi Dress
superdown Avya Maxi Dress
The Sensible Shoe
One thing about Carolyn? You'll never catch her in a sky-high platform (and my arches thank her for that!). While she often donned a sleek slingback heel for special events, her everyday footwear rotation consisted of down-to-earth styles like functional knee-high boots and loafers. Her go-to Prada styles cost a pretty penny, so I've pulled some lookalikes from Dolce Vita and Sam Edelman that'll get just as much mileage in your wardrobe.
Madewell The Grayson Penny Loafer
Dolce Vita Tiggy Loafer
Sam Edelman Sylvia Knee High Boot
Lauren Gruber is an commerce editor at Hearst Magazines, where she writes for publications like Good Housekeeping, Cosmopolitan, Prevention, Country Living, House Beautiful, and more. She has over four years of professional experience covering a variety of lifestyle topics from home to fashion, with an advanced background in beauty and fragrance. When she’s not researching the most worthy Prime Day deals or hands-on testing all the latest perfume launches, Lauren is probably hanging out with her cat Serafina or flexing her AMC A-List membership at the movie theater. You can find her previous work at Entertainment Tonight, Shop TODAY, USA Today, Self Magazine, L’Officiel USA, V Magazine, and Modern Luxury Media.
