If you’ve spent the past few weeks inhaling all things Carolyn Bessette Kennedy, you’re certainly not alone. The ’90s publicist and perennial style reference has quietly reclaimed her place on fashion feeds, sparked by the TV show centred around her relationship with John F. Kennedy Jr. in Love Story. Suddenly, my algorithm is filled with slip dresses, razor-sharp coats and grainy paparazzi images that all point to the same conclusion: CBK’s wardrobe feels more relevant than ever. Built not on statement pieces or passing trends but on simplicity, her style revolved around minimal, timeless essentials—impeccable outerwear, simple shirting and one very specific pair of jeans.
(Image credit: Getty Images)
Frequently photographed in Levi’s bootcut jeans— particularly the 517s, a style originally designed for men—Bessette Kennedy made the silhouette entirely her own, turning practical denim into something undeniably refined. Still in stock and now reworked in women’s cuts, the bootcut delivers the same clean lines CBK made iconic, no vintage hunting required. The cut is deceptively simple: slim through the hips with a subtle flare that skims over shoes, creating a long, uninterrupted line. Styled with tucked-in white shirts, fine knits and sweeping wool coats, sharp loafers and leather boots, the jeans anchored her outfits, adding polish to looks that might otherwise have felt too pared back.
(Image credit: Getty Images)
After years dominated by exaggerated proportions and overtly nostalgic denim trends, the bootcut reads polished, balanced and quietly confident; the kind of jean that slips seamlessly between tailoring, heels and ballet flats. Its return feels less like a revival and more like a reminder that the strongest wardrobes are often built on the simplest foundations. Keep scrolling to shop CBK’s exact Levi’s jeans.
Shop Carolyn Bessette Kennedy’s Levi Jeans
A modern reinterpretation of the 517 Levi’s captures the same vintage attitude. Slightly higher rise and sculpting through the waist give this pair that polished, off-duty model energy CBK perfected.
Levi
725 High Rise Bootcut Jeans
A streamlined, leg-lengthening take that feels especially wearable with tailoring and heels—ideal if you want the CBK look with a slightly more modern fit.
Levi
517™ Bootcut Jeans
The exact silhouette Carolyn Bessette Kennedy wore on repeat. Originally designed for men, the 517 sits clean through the hip with a subtle kick flare, understated, elongating and unmistakably ’90s.
Levi
315™ Shaping Bootcut Jeans
Soft stretch denim makes these an easy everyday option, while the clean dark wash keeps things feeling elevated rather than casual.
Shop More ’90s Minimalist Bootcut Jeans
MANGO
Violet Flared High-Rise Jeans
A slightly more pronounced flare that channels the same minimalist energy, especially styled with sharp coats and simple knits.
AGOLDE
+ Net Sustain 90’s Pinch Waist Long High-Rise Straight-Leg Organic Jeans
A premium, editor-loved option that captures the same high-rise, vintage simplicity CBK made her signature.
hm
Bootcut Regular Jeans – Denim Blue
Cut slim through the hips before gently flaring from the knee, this pair recreates the same clean, leg-lengthening silhouette that made CBK’s Levi’s feel so refined.
COS
Reprise Straight-Leg Jeans
Less bootcut more straight-leg, with the same kind of clean, architectural style that aligns perfectly with Bessette Kennedy’s pared-back wardrobe approach.
& Other Stories
Slim Low-Rise Bootcut Jeans
The low-rise waist and slim fit through the hips give these jeans an authentic late-’90s feel, while the gentle bootcut flare keeps the silhouette long and polished rather than overtly retro.
ZARA
Zw Collection Bootcut Mid-Waist Jeans
Clean lines and a minimal wash make these feel very CBK-coded—easy, unfussy and ideal with a white shirt.
For those who prefer a longer silhouette, this pair leans into the elongating effect that made bootcuts so iconic in the first place.
If CBK’s 517s are the reference, this is the fashion-forward evolution. Designed with Levi’s highest rise to define the waist and a vintage-inspired bell flare, the fit is slim through the thigh before kicking out dramatically, creating that leg-lengthening line editors consistently return to.
M&S
High Waisted Flared Jeans
A polished high-street interpretation of the ’90s bootcut mood.