Carolyn Bessette Kennedy Will Always Be My Style Muse—5 Iconic Looks to Emulate in 2026
I've been through the archives—these 5 Carolyn Bessette Kennedy outfits look just as chic in 2026.
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
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.
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Layer this over a white tee or style this on its own.
Be quick! This is on its way to selling out.
These also come in ruby and black.
This is the perfect size for carrying around your daily essentials.
2. The Sleek Black Coat
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.
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A sleek, tailored black coat will never go out of style.
The cashmere composition ensures a cosy finish.
The square-toe finish gives these such a polished feel.
Shield your eyes in style.
DeMellier's bags are a fashion person's favourites.
3. The Flared Jeans
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.
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This lightweight coat is perfect for early-spring styling.
A sleek brown headband is always a chic idea.
Style these with loafers to get Carolyn's look.
These chocolate brown loafers are such an elegant alternative to typical black pairs.
4. The Slip Dress + Jacket
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:
Style with a long-line jacket to get Carolyn's look.
The tailored finish makes this perfect for weekday styling
These also come in dark brown.
5. The Button-Down
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.
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With Nothing Underneath's Boyfriend shirts are some of the very best on the market.
The pencil skirt trend isn't showing any signs of slowing down.
Rabanne's chainmail bags will never go out of style.
