3 min readHulu and FX’s Love Story, which chronicles the whirlwind romance of John F. Kennedy Jr. and Carolyn Bessette Kennedy, is reaching its end. While I’m eager to see how the story concludes through the series’s lens, I can’t help but notice the renewed fascination with Bessette Kennedy’s impeccable ’90s style.
It’s hardly surprising—she worked at Calvin Klein, lived in New York, and clearly understood the power of timeless, understated dressing. Decades later, that same sensibility still resonates, with many of us attempting to capture her effortless elegance, whether through her pared-back beauty regimen, her well-curated wardrobe, or even her signature fragrances.
It’s evident that her appeal has proven remarkably lasting. While there’s no shortage of cold-weather inspiration—from polished trench-and-denim pairings to sleek evening wear—it raises the question: What did CBK wear when the city heated up? Did she gravitate toward airy sundresses, relaxed linen sets, or sharply tailored shorts paired with crisp blouses? Curious, I revisited her ’90s street style and found a range of warm-weather looks that feel just as stylish today. If you’re looking to channel that same understated allure for the summer months, consider this your guide—scroll on for plenty of chic inspiration.
A Floral Dress and Chic Black Accessories
Carolyn Bessette Kennedy was known for her preference for dark, monochromatic dressing, which is precisely why this look stood out. She stepped out in a floral Chanel dress from the designer’s spring/summer 1996 collection, featuring an elegant V-neck and a just-below-the-knee hemline. To accessorize, she completed the look with sleek black slingback pumps and a classic patent Prada tote—proof that even the most dedicated minimalists can embrace a touch of florals when the mood (and weather) calls for it.
Marc Jacobs Mini Grind Tote Bag
Now 67% Off
Charles & Keith
Pointed Slingback Pumps
Jenny Bird
Lennon Mini Hoop Earrings
Bobbi Brown Long-Wear Cream Shadow Stick
Now 15% Off
A Knit Tank with Cropped Jeans
On warm spring days, you really can’t miss with an easy combination like relaxed denim and a simple tank. Bessette Kennedy chose a pair of cool, cropped jeans that perfectly showcased her Prada Tobacco Capretto sandals. True to her signature minimalism, she finished the look with just a small, sleek watch.
A Button-Up Shirt, Straight-Leg Pants and a Raffia Tote
A partially unbuttoned, untucked button-down is a fail-safe way to channel the style icon’s understated, nonchalant ease. In these photos, she paired a breezy, navy blue shirt with simple, straight-leg pants and chic black heeled loafers. While Bessette Kennedy was often seen carrying a classic black tote, here she opted for an oversized raffia version, lending the ensemble an even more effortless feel.
Eileen Fisher Organic Linen Button-Up Shirt
Polo Ralph Lauren
Stretch-Cotton Beaton Pant
Sensi Studio
Large Straw Tote
Bared Footwear
Alethe Loafer
Banbe
The Selena Sunglasses
An Oversized Shirt, White Pants and Sneakers
Though often seen in loafers or other similarly polished footwear, Bessette Kennedy had a clear appreciation for comfort. For a sunny city stroll, she embraced a sportier look—styling crisp white cotton pants with Nike Air Streak sneakers, an oversized black button-up, and sleek black oval sunglasses.
Leset
Yoko Oversized Button Down
Nike
V5 RNR Runner
Now 30% Off
& Other Stories
Slim Oval-Frame Sunglasses
Shop More Carolyn Bessette Kennedy-Inspired Spring Staples
J.Crew Ballet-Sleeve Top
Now 40% Off
J.Crew Cosmo Pant
Now 40% Off
Rixo
Carey Linen Midi Dress
With Nothing Underneath
The Classic Shirt
Mother
The Mid Rise Dazzler Ankle
Sézane
The Tote
Now 51% Off
Lauren by Ralph Lauren
Khloe Leather Slingback Loafer Pump
Fossil Mini Raquel Tank Leather Strap Watch
Why Trust ELLE
Every product featured on ELLE.com is independently researched, tested, or editor-approved. We only recommend products that we stand behind, and the merchandise featured on our site is always driven by editorial and product testing standards, not by affiliate deals or advertising relationships. Any content created in partnership with advertisers is marked as such.