I’m not going to lie. I had my doubts about Love Story, Ryan Murphy’s series on FX about Carolyn Bessette and John F. Kennedy Jr. I, like so many others spanning all generations, feel an attachment to the couple, particularly to Bessette. She’s been my number one style inspiration for much of my life not because of the labels she wore but because of how she wore clothes. She dressed with ease and elegance, whether she was donning jeans and flip-flops in Cape Cod or attending a museum gala on the Upper East Side. The paparazzi photos taken from the set of the series nearly ruined it for me, but I’m glad I gave it a chance. It is just right—so much so that I cannot stop watching. This, in turn, has transformed my Instagram feed to be even more CBK-focused than normal.
While I wait for episode 4 to drop, I thought I’d use my time wisely and get to work sourcing pieces that check off those same boxes that Bessette’s style always achieved. Much of her wardrobe was made up of classic, elevated basics, but she also wasn’t afraid to test the boundaries, adding in more artistic pieces by Yohji Yamamoto and the occasional bold print, from leopard to plaid. The curation below is meant to mimic that balance as well as modernize it, including all 2026 pieces that could still feel at home in Bessette’s closet. Keep scrolling to shop all 31 items on my Carolyn Bessette–inspired timeless shopping list for 2026, from Calvin Klein and Prada to Kallmeyer and Toteme.
A CBK-Inspired Timeless Shopping List for 2026
CALVIN KLEIN COLLECTION
Parker Wool Blazer
I’ve been in love with this collarless blazer since it debuted on the runway. Though the shape is a bit boxier than what Bessette preferred in the ’90s, I think she would have loved the interesting shape.
ARCH4
Cassie Cable-Knit Silk and Organic Cashmere-Blend Tank
This cashmere-silk sleeveless knit is a dream, whether you pair it with a pencil skirt like it’s styled above or with Bessette’s favorite jeans, Levi’s 517s.
TOTEME
Garderob Organic Low-Rise Straight-Leg Jeans
These jeans have a similar look with subtle flaring at the bottom, but they have a lower waist, which is becoming more and more popular in 2026.
Jimmy Choo
Eliot Slipper 45
I can’t stop thinking about these perfect Jimmy Choo leopard-print loafers. They remind me of Bessette’s iconic snakeskin heeled loafers by Prada and are perfect with jeans and a sweater.
Lisa Yang
Rhea Cashmere Cardigan Coat
For a chilly morning at the Cape, I can totally see modern-day Bessette wearing this maxi cardigan coat by Lisa Yang with jeans and flip-flops.
Sophie Buhai
Thin Bessette Headband
Duh. It’s literally called the Bessette Headband.
TOTEME
Strapless Crepe Maxi Dress
This dress is so Carolyn Bessette coded, both IRL and in the show, Love Story. The real Bessette wore one like it with long velvet opera gloves, but in the show, Sarah Pidgeon donned the Calvin Klein strapless frock more simply. I can actually see her wearing it with this jacket and these loafers as well for a more dressed-down, day-after look.
JIL SANDER
Goji Pillow Small Crinkled-Leather Shoulder Bag
Since I already own and love the reissued version of Bessette’s favorite Prada from 1995, I thought I’d look into another shoulder bag that feels like her. I adore the kiss-lock closure on this Jil Sander alternative.
BLAZÉ MILANO
Jealousy Sussex Cotton-Velvet Midi Skirt
Skirts were an area where Bessette had a bit of fun, so I feel like she’d be very into this chocolate-brown velvet column skirt from Blazé Milano. The texture and color create such a rich piece.
Mikimoto
Akoya Pearl Stud Earrings
Bessette rarely wore jewelry, but when she did, it was usually just a simple pair of pearl studs.
FLORE FLORE
Esmé Ribbed Organic Cotton-Jersey Tank
A classic, elegant tank top to style with jeans, skirts, and more.
HIGH SPORT
Long Kick Stretch-Cotton Flared Pants
I think Bessette would have loved High Sport. Its pants are so easy to toss on and look sophisticated in.
Manolo Blahnik
Carolyne Genuine Calf Hair Slingback Pump
A classic choice that makes every outfit better.
Saint Laurent
Midnight Large Clutch in Smooth Leather
CALVIN KLEIN COLLECTION
Luna Satin Skirt
This satin pencil skirt would have gotten so much wear at the Calvin Klein office.
Saint Laurent
Francoise Smooth Leather Knee-High Boots
COLLEEN ALLEN
Cutout Knit Turtleneck Top
A simple turtleneck in the front, a daring statement in the back.
Khaite
Empire Leather Belt
Though she loved her classic blue 517s, Bessette wasn’t afraid to venture out into other denim options, like khaki and brown jeans.
JAMIE HALLER
Mod Calf Hair and Glossed-Leather Loafers
Jamie Haller’s loafers are beloved by fashion people everywhere for their sleek look and ultra-comfortable fit.
TOM FORD
Iggy Oval-Frame Acetate Sunglasses
The blue lenses are a stretch, but I think modern-day Bessette would be down to try them.
NOUR HAMMOUR
Leopard-Print Calf Hair Coat
I mean, I had to include this incredible Nour Hammour coat in leopard-print pony hair.
Cartier
Tank Louis Cartier Watch
Another piece of jewelry Bessette made an exception for: Cartier’s Tank watch.
Polo Ralph Lauren
The Iconic Flag Sweater
Everyone thinks of Carolyn Bessette’s city style, but her laid-back looks at the beach were just as chic.
Prada
Large Leather Tote Bag
We usually saw Bessette carrying a black bag, but I think she would have loved this cognac Prada tote, at least once she beat it up a little.
Monica Vinader
Nomade Pearl Necklace
Pearls were her thing, clearly.
CALVIN KLEIN COLLECTION
Anita Off-the-Shoulder Wool-Blend Dress
The elegance! I can’t stand it.
TOTEME
Patent-Leather Slingback Pumps
I get the feeling that these would have been heavy in Bessette’s 2026 rotation—just like they will be in mine.
Polo Ralph Lauren
Cotton Oxford Long Sleeve Buttondown
Perfect for tucking into skirts and jeans.
Maison Margiela
Textured Rib Mesh Midi Skirt
Maybe this is a stretch, but I think the cool texture of this skirt would have called out to Bessette, especially in her younger years.
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