As a fashion editor with a longstanding love for ’90s minimalism, Carolyn Bessette Kennedy is rarely far from my mind, and never missing from my moodboard.
With a background in publicity at Calvin Klein, Carolyn’s personal aesthetic closely mirrored the brand’s sleek, polished silhouettes that defined an era. Clean lines, muted palettes and impeccable tailoring ran through her wardrobe, but I find the most compelling thing about Carolyn’s style is that she understood restraint in a way that still feels instructive today.
As FX releases its highly anticipated Love Story, chronicling Carolyn and JFK Jr.’s relationship, I’ve found myself revisiting her archive once again. Below, I’ve pulled five enduringly chic looks that feel just as relevant now as they did in the mid-’90s.
Discover some of Carolyn’s chicest looks below.
5 Archival Carolyn Bessette-Kennedy Looks to Copy Now
1. The Pencil Skirt
(Image credit: Getty Images)
Style Notes: Knee-length pencil skirts have enjoyed renewed relevance in 2026, but Carolyn was already paving the way in the mid-’90s. Wearing hers with a fine knit and a pair of knee-high boots, despite the strict skirt, Carolyn’s outfit felt perfectly coordinated yet pleasantly unfussy—as all of her looks managed to do.
Shop the Look:
Marks & Spencer
Pure Merino Wool V-Neck Jumper
Layer this over a white tee or style this on its own.
Be quick! This is on its way to selling out.
Reformation
Claudette Knee Boot
These also come in ruby and black.
This is the perfect size for carrying around your daily essentials.
2. The Sleek Black Coat
(Image credit: Getty Images)
Style Notes: If I were rebuilding my capsule wardrobe from the ground up, a sleek, tailored coat would be my starting point—and Carolyn would be the blueprint. While wool iterations are handy during the colder months, she often leaned into lighter, fluid fabrics. Worn over an all-black base, the longline coat did all the heavy lifting.
Shop the Look:
A sleek, tailored black coat will never go out of style.
Reformation
Jett Cashmere Turtleneck
The cashmere composition ensures a cosy finish.
& Other Stories
Knee-High Nappa Sock Boots
The square-toe finish gives these such a polished feel.
Shield your eyes in style.
DeMellier
The Stockholm Bag
DeMellier’s bags are a fashion person’s favourites.
3. The Flared Jeans
(Image credit: Getty Images)
Style Notes: Though she was more frequently photographed in skirts and tailored trousers, when Carolyn wore denim, her preference was a subtle kick flare, cropped neatly at the ankle. The shorter hemline gave the silhouette a lighter finish—particularly when paired with sleek leather loafers and a knee-grazing coat.
Shop the Look:
This lightweight coat is perfect for early-spring styling.
& Other Stories
Wide Classic Headband
A sleek brown headband is always a chic idea.
Mango
Sienna Flared Cropped Jeans
Style these with loafers to get Carolyn’s look.
Massimo Dutti
Embossed Leather Loafers
These chocolate brown loafers are such an elegant alternative to typical black pairs.
4. The Slip Dress + Jacket
(Image credit: Getty Images)
Style Notes: Few could make a throw-on dress feel as refined as Carolyn. Layering her knitted style beneath sharp tailoring, Carolyn grounded her outfit with tall knee-high boots. From there, finishing touches—her iconic tortoiseshell headband and slim sunglasses—added enough interest without disrupting the look’s simplicity.
Shop the Look:
Massimo Dutti
Strappy Midi Dress
Style with a long-line jacket to get Carolyn’s look.
Asos Design
Longline Formal Coat
The tailored finish makes this perfect for weekday styling
Reformation
Raven Knee Boot
These also come in dark brown.
5. The Button-Down
(Image credit: Getty Images)
Style Notes: If anyone understood the power of a capsule wardrobe, it was Carolyn. Making simpe white shirts feel impossibly cool, Carolyn styled hers with a longline black skirt for contrast, whilst a gold chainmail bag energised her look.
Shop the Look:
With Nothing Underneath
The Boyfriend Shirt
With Nothing Underneath’s Boyfriend shirts are some of the very best on the market.
Marks & Spencer
Knitted Midaxi Column Skirt
The pencil skirt trend isn’t showing any signs of slowing down.
Rabanne
1969 Nano Chainmail Shoulder Bag
Rabanne’s chainmail bags will never go out of style.
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