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A Shopping Guide To JFK Jr. And Carolyn Bessette-Kennedy’s Most Iconic Couple Fits

Home> Lifestyle

Updated 15:02 24 Feb 2026 GMTPublished 19:47 6 May 2025 GMT+1

A Shopping Guide To JFK Jr. And Carolyn Bessette-Kennedy’s Most Iconic Couple Fits

Couple goals meets quiet luxury.

Marissa Dow

Marissa Dow

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I’m hearing the kids are obsessed with lore these days, and yet I’m not seeing enough appreciation for the truly iconic (like, for once, I’m not exaggerating or being ironic) relationship between John F. Kennedy Jr. and Carolyn Bessette.

JFK Jr. (or as some people named Sonja Morgan allegedly called him, Jack-Jack, IYKYK) was the son of John F. Kennedy and Jackie Kennedy Onassis. He was born in 1960, just a year before his dad would become president and a few years before his father would tragically die by assassination in 1963.

Years later, when JFK Jr. was 32, he had a movie-worthy meet-cute with a PR professional working for Calvin Klein, who not only sold him a few suits in a private dressing room but also stole his heart. This, of course, would be one Carolyn Bessette, a blonde with a head of hair that wouldn’t quit and a personality constantly described by friends (like Carole Radziwill because, yes, old RHONY was simply that bitch) as nothing less than infectious.

They were married in an intimate waterfront ceremony in 1996, and though their marriage was documented to face some serious challenges, their relationship became a symbol of storybook love that met its own tragic end due to a plane crash on July 16, 1999. Before their premature passing, JFK Jr. and Carolyn’s magic seemed to manifest in incredible fashion choices. When it comes to cool-girl style, Carolyn is the blueprint, and together, their timeless summery aesthetic was defined by serves I can’t stop thinking about. Carolyn Bessette and JFK Jr.’s best fashion moments are the elevated couple’s inspo you’ve been looking for.

Betches may receive a portion of revenue if you click a link and purchase a product or service. The links are independently placed and do not influence editorial content. Prices are accurate at the time of publication.

JFK Jr. And Carolyn Bessette Style

Alo Make Waves Hoodie

This oversized hoodie is the perf mixed-up monochrome moment that elevates athleisure. Plus, it’s on sale.

Alo Make Waves Hoodie

$158

$110

Shop Now

Women’s Squall Packable Waterproof Raincoat

You want timeless, long-lasting pieces? Shop at timeless companies like Lands’ End, babe!

Women's Squall Packable Waterproof Raincoat

$149.95

$109.99

Shop Now

South Beach striped swim shorts in cherry red

These are chic enough for your man to wear to the beach or in the streets.

South Beach striped swim shorts in cherry red

$35

$28

Shop Now

Aerie Good Day Cover Up Short

And, just in case you want to outdo him, here are some adorable board shorts by Aerie for the girls.

Aerie Good Day Cover Up Short

$39.95

$10

Shop Now

JFK Jr, Carolyn Bessette Kennedy
JFK Jr, Carolyn Bessette Kennedy
Image Credit: Getty Images

Straw Shoulder Bag

Obsessed with how wearable (and affordable) this summer shoulder bag is!

Straw Shoulder Bag

$24.99

Shop Now

JFK Jr, Carolyn Bessette Kennedy
JFK Jr, Carolyn Bessette Kennedy
Image Credit: Getty Images

Deluxe Desire Red Tweed Long Sleeve Blazer Mini Dress

With the right styling, this will look so expensive.

Deluxe Desire Red Tweed Long Sleeve Blazer Mini Dress

$88.00

$53.00

Shop Now

TRUE BEANIE AND SCARF SET

For the guys and girls who want to be New England-level cozy for the frosty months.

TRUE BEANIE AND SCARF SET

$89

$29.99

Shop Now

JFK Jr, Carolyn Bessette Kennedy
JFK Jr, Carolyn Bessette Kennedy
Image Credit: Getty Images

ONLY Long Sleeve Asymmetric Button Shirt

The white button-down is the final boss of looking elegant and casual at the same time. This wraparound style from ASOS is a dead ringer for CB’s fit.

ONLY Long Sleeve Asymmetric Button Shirt

$63

$53.55

Shop Now

Steve Madden Cary Black Leather

When your boyf asks if you really need another pair of kitten heels, the answer is yes, and these stunners from Steve Madden, specifically.

Steve Madden Cary Black Leather

$79.95

Shop Now

JFK Jr, Carolyn Bessette Kennedy
JFK Jr, Carolyn Bessette Kennedy
Image Credit: Getty Images

New Balance 574 unisex sneakers

In a world full of intentionally scuffed beige walking sneakers, be retro blue.

New Balance 574 unisex sneakers

$90

Shop Now

ASOS DESIGN knit slash neck textured rib knit sweater in cream

This sweater is a year-round ticket from cozy town since it works for a beach sunset walk or bumping elbows walking down 6th Ave.

ASOS DESIGN knit slash neck textured rib knit sweater in cream

$49.99

$29.99

Shop Now

Steve Madden What the Fuzz Beret

A beret feels hard to pull off, but a) just wear matching neutral colors, and b) are you really gonna say you never tried on your deathbed???

Steve Madden What the Fuzz Beret

$36

$14.97

Shop Now

JFK Jr, Carolyn Bessette Kennedy
JFK Jr, Carolyn Bessette Kennedy
Image Credit: Getty Images

Wide tortoise shell headband

It’s so Carolyn, Charlotte, and Blair at once.

Wide tortoise shell headband

$34.50

$24.50

Shop Now

UO Essential Oval Sunglasses

Just looking at these, I’ve never felt cooler.

UO Essential Oval Sunglasses

$15.00

Shop Now

Everlane The Mac Coat

Another (sustainably made) staple piece your capsule collection kinda needs!

Everlane The Mac Coat

$248

$62

Shop Now

Vera Bradley Women’s Quilted Scarf

I, for one, will be draping myself in this on freezing (60-degree) LA nights for the foreseeable future.

Women's Quilted Scarf

$31.23

$24.92

Shop Now

Topman Oversized Double-breasted Cord Suit Jacket

Pro tip: If you order this for your guy, you can immediately steal it for an oversized look whenever you want.

Topman Oversized Double-breasted Cord Suit Jacket

$189

$94.50

Shop Now

JFK Jr, Carolyn Bessette Kennedy
JFK Jr, Carolyn Bessette Kennedy
Image Credit: Getty Images

Tan Leather Midi Skirt

This skirt is the first step to a cunty corporate slay, if you will.

Tan Leather Midi Skirt

$34.99

Shop Now

Steve Madden Downtown Brown Leather

Something about a sexy square toe just ties this whole vibe together.

Downtown Brown Leather

$169.95

Shop Now

JFK Jr, Carolyn Bessette Kennedy
JFK Jr, Carolyn Bessette Kennedy
Image Credit: Getty Images

The A&F Paloma Long-Sleeve Mini Dress

Endlessly flattering and easy to style, like with tall boots in the fall as Carolyn has it here, or sneakers and a baseball cap for a sporty spring look.

Paloma Long-Sleeve Mini Dress

$80.00

$59.99

Shop Now

’47 Brand MLB Los Angeles Dodgers Team Logo Clean Up Hat

Help him accessorize without looking like a dad who got lost in a Sears!

’47 Brand MLB Los Angeles Dodgers Team Logo Clean Up Hat

$29

Shop Now
Featured Image Credit: Getty Images

Topics: Celebrity Fashion, Fashion, Shopping, Style

Marissa Dow
Marissa Dow

MARISSA is a trending news writer at Betches. She's more than just another pop-culture-addicted-east-coaster-turned-LA-transplant...she's also an upcoming television writer and aspiring Real Housewife (whichever comes first). Live, laugh, balegdah.

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