Anything “throw-back” is all the rage when it comes to fashion. From 2020’s 70s-styled scrunchies and high-waisted mom jeans, to the “90s-fine” aesthetic, and 2016 makeup, social media’s infatuation with decades fashion is no stranger to trending. This year, in 2026, minimalism is back; less is more. With the premiere of Hulu’s new series, Love Story: John F. Kennedy Jr. & Carolyn Bessette, the world of fashion is bursting with admiration for Mrs. Carolyn Bessette-Kennedy’s timeless wardrobe. With many media platforms describing her as chic and minimalist, let’s dive into some of her most iconic wardrobe pieces.
- Statement Outerwear
-
Any New Yorker knows that a good coat is a must for braving the snow, wind, and rain in the big city. As a fashion publicist with Calvin Klein, Carolyn Bessette-Kennedy was no stranger to fashion, even when it came to battling the elements. Much of Bessette-Kennedy’s wardrobe included longer coats, in muted tones of both camel and black, but also patterns. One of her most iconic pieces: her plaid, red and white Prada Coat.
Find Similar Looks At:
- ZARA: Long Belted Water Repellent Windproof Trench Coat $119.00
- Jack Hafford: Charlotte Cashmere Coat (red and white plaid) $249.99 (discounted at $149.00 as of Feb. 28).
@carolynbeessetehd on Instagram - Tortoiseshell Headband
-
One of CBK’s most reputable pieces is her iconic headband, which she’s been spotted wearing in multiple paparazzi clips. The Charles J. Wahba headband itself is rumored to have been purchased from a local New York City apothecary in Greenwich Village, C.O. Bigelow. An accessory made for versatility, this tortoiseshell headband goes with any up-do, but also pairs nicely with flowing hair.
Find Similar Looks At:
- Amazon: Parcelona French Wide Headband $10.50
- Amazon: Parcelona French Extra Wide Headband $12.95
@cbk.icon on Instagram - Kick-Flare Jeans
-
Bessette-Kennedy never failed to strut in a pair of pants that didn’t accentuate the rest of her outfit. Her iconic kick-flare jeans are a 90s version of the 70s re-known bellbottom jeans. This slimmed version leaves room to take a moment for the shoes—as they hit about mid-ankle—but also hugs the hips and adds depth for pairing with a good basic top (another CBK favorite).
Find Similar Looks At:
- American Eagle: AE Next Level High-Waisted Kick Bootcut Jeans $37.46
- Quince: Bella Stretch Wide Leg Jeans $50.00
@the_twomrs on Instagram - Basic Staple-Tops
-
Every girl’s wardrobe needs a good rotation of basics. These basics are the canvas to your outfit, an art that Bessette-Kennedy mastered tastefully. Many of her outfits were built off a solid foundation of minimalist tops, A.K.A “basic staples.” These staples include white, black, brown, and other neutral tops, ranging from button-ups, turtlenecks, and V-necks to cashmere.
Find Similar Looks At:
- H&M: 2-pack T-shirts $9.99
- Old Navy: Classic Button-Down Shirt $20.99
- Uniqlo: HEATTECH Cashmere Blend T-Shirt | Extra Warm | Turtleneck $29.90
@cbk.icon on Instagram - The Sunglasses
-
A sight for sore eyes, CBK’s iconic oval sunglasses by Selima Optique are one of her most featured pieces in photos. Sunglasses are the perfect way to upscale an outfit, especially if you play your cards right and choose the right shape. Bessette-Kennedy’s choice of oval lenses offers just the right amount of coverage without taking away from her facial features, while also leaving room for the rest of the outfit to shine.
Find Similar Looks At:
- H&M: Oval Sunglasses $12.99
- Princess Polly: Wonderful World Sunglasses Black $20.00
- Optical Factor: Lauryn Oval Sunglasses $20.95
@fashionarchives__ on Instagram - Black Birkin
-
Regularly spotted with her Black Birkin in hand, Bessette-Kennedy used her bag the way Jane Birkin intended for it to be used: “There’s no fun in a bag if it’s not kicked around…” CBK donned her iconic bag in paparazzi photos while leaving work or simply moving about New York City. A functional bag for a busy lady in the eyes of the media and the fashion industry.
Find Similar Looks At:
- Wanderlust Studio: Women’s Handbag, Togo Leather, Top Handle, Cross-body with shoulder strap $119.99
- ALDO: Alicietotee $78.00
@cbk.icon on Instagram - Manolo Blahniks
-
An obvious fan of a clean, chic look, Bessette-Kennedy admired the Italian craftsmanship of Manolo Blahnik. Spotted on errands in a pair of Manolo Blahnik flats, CBK’s admiration for minimalistic fashion extends all the way down to her footwear. Another popular wear for Carolyn Bessette-Kennedy was the Manolo Blahnik Carolyne, a kindred shoe to her popular black Manolo flats. They were a short, high-heeled shoe perfect for pairing with dresses and formal wear.
Find Similar Looks At:
- Target: Women’s Elle Slingback Pointed Toe Heels $36.00
- Michael Kors: Amali Slingback Flat $165.00 (discounted at $79.00 as of Feb. 28)
- ZARA: Leather Slingback Shoes $79.90
@cbk_closet on Instagram - Black Midi-dress
-
From casuals to formals, Carolyn Bessette-Kennedy covered all bases when it came to being tastefully dressed for any occasion. A fan of Prada for their purses and outerwear, CBK also ventured to strut an iconic Black Prada Silk dress while out on the town. Her date-night dress of choice became a hit with the media and became known as “the Little Black Dress,” an all-time favorite.
Find Similar Looks At:
- ZARA: Strappy Midi Dress $59.90
- Quince: 100% Washable Silk Slip Dress $89.90
@muted_vintage on Instagram - Tall Boots
-
As much as she loved her Manolo Blahniks, Carolyn Bessette-Kennedy had a taste for more than just one variety of shoe. She was regularly spotted sporting a pair of tall boots, with either a pencil skirt or her iconic jeans. Many photos show her in a pair of either black or brown Prada boots while walking the streets of New York.
Find Similar Looks At:
- DSW: DV By Dolce Vita Flapper Boot $99.00 (discounted at $64.98 as of Feb. 28)
- Macy’s: Tommy Hilfiger Women’s Ursy Tall Block Heel Boots $159.00 (discounted at $47.70 as of Feb. 28)
@muted_vintage on Instagram - Cartier Tank Watch
-
A girl can have all the shoes, clothes, hair, and makeup done, but her jewelry is the final touch — the cherry on top. Bessette-Kennedy, in her own fashion, remained true to her style and wore a Cartier Tank Watch. The thin black strap, square-faced watch, with gold accents, is the perfect timeless piece. Not too bulky, but also not too subtle that you’d miss it, the Cartier Tank Watch was the “pizzazz” that completed an outfit for the fashionable Carolyn Bessette-Kennedy.
Find Similar Looks At:
- Peugeot: Women’s Tank Watch Roman Dial Black Leather Strap $90.00 (discounted at $59.75 as of Feb. 28)
- Caducci: Bella Leather Watch $100.00 (discounted at $59.95 as of FEb. 28)
@cbkalifeinfashion on Instagram
A trend-setter who left her mark on fashion, Carolyn Bessette-Kennedy will be remembered for her grace in style. In an interview by Glamour in 1992, Bessette-Kennedy shared, “I’m not comfortable with anything ornate, I like clean, understated looks.” Her admiration for simplicity in fashion is the epitome of “less is more” as a rule of thumb for vogue. With a wardrobe overflowing with influence over the last two decades, CBK will always be admired as the fashion industry’s American Princess.