Here’s how to recreate Carolyn Bessette-Kennedy’s iconic ’90s style

The Curator independently decides what topics and products we feature. When you purchase an item through our links, we may earn a commission. Promotions and products are subject to availability and retailer terms.

Before “quiet luxury” became a buzzword, there was Carolyn Bessette-Kennedy. With her slinky slip skirts, tortoiseshell headbands and crisp white blouses, she mastered the art of looking impossibly polished without ever appearing overdone. Whether she was navigating Manhattan streets alongside John F. Kennedy Jr. or getting glam for a gala, her wardrobe was a lesson in restraint–and confidence. Her iconic ’90s style is enjoying a resurgence thanks to Ryan Murphy’s Love Story series–and you better believe we’ve been tuning in. Ahead, modern staples from Aritzia, Simons, L.L. Bean and beyond that feel quintessentially Caroline.

Susie Wall’s picks:

Shimmery Wide Headband

Bessette-Kennedy rarely left home without a sleek Lucite tortoise headband anchoring her glossy blonde hair. This chunky, minimalist style delivers that same polished effect. Wear it with a bare face and tailored separates for that uptown, off-duty energy she perfected.

$4.99 at Simons

Babaton Letterpress Classic Poplin Shirt

If there was one piece she made iconic, it was the crisp white blouse. Slightly oversized, impeccably pressed and styled with denim or a satin skirt, it was her uniform. This structured poplin button-down captures that same clean-lined ease–sharp enough for the Calvin Klein office, relaxed enough for weekend coffee runs with JFK Jr.

$98 at Aritzia

Boat and Tote Zip Top

Bessette-Kennedy’s large carryalls balanced her otherwise refined outfits. This canvas zip-top tote channels that practical-meets-polished sensibility. Roomy and understated, it’s the kind of bag you’d sling over your shoulder with boot-cut jeans and a black knit–dog leash in hand, camera flashes optional.

$70 at LL Bean

You may also like:

OPI GELement in Glazed Donut – $15.99

Dream Pairs Women’s Chelsea Ankle Boots – $65.99

Slouchy Suede Shoulder Bag – $15.08

More Carolyn Bessette-Kennedy-inspired outfit ideas

'90s Vintage Shades

Tiny, oval sunglasses were her calling card–often sourced from Selima Optique in NYC. These slim, minimalist frames instantly evoke that downtown cool factor. Pair them with a slick bun and neutral layers for peak ’90s nostalgia.

$8.9 on Amazon

Levi's Womens 318 Shaping Wide-Leg Jeans

Long before the reign of the skinny jean, Bessette-Kennedy made boot-cut denim look impossibly chic. She styled hers with heeled boots and tailored coats, proving jeans could feel dressy. This flattering, leg-lengthening pair delivers that same elongating silhouette–just add a black belt.

$92.95 on Amazon

JW PEI Women's Hana Medium Faux Suede Tote Bag

Slouchy, oversized handbags were a key part of her off-duty formula. This slouchy suede tote feels luxurious yet undone—exactly the kind of accessory that complements, rather than competes with, a minimalist wardrobe like Bessette-Kennedy’s.

$186 on Amazon

Bellivera Faux Leopard Fur Coat

Arguably her most famous street-style moment: that leopard-print coat worn on a stroll with JFK Jr., styled with blue jeans and black heeled boots in a way that felt quintessentially Carolyn. The original vintage design may be archival, but this faux-fur version captures the same high-low magic.

$87.99 on Amazon (was $95.39)

Ralph Lauren Lolah Leather Slingback Pumps

Slingbacks were a natural extension of her chic aesthetic–feminine but never fussy. This pointed-toe pair sharpens everything from denim to slip skirts, echoing her ability to elevate even the most casual pieces.

$180 at Simons

Babaton Slip Satin Maxi Skirt

The satin slip skirt was a ’90s staple she wore with knits, blouses and everything in between. This oh-so-fluid maxi version glides with every step. Balance the softness with a structured coat or crisp shirt for that signature tension she mastered so well.

$98 at Aritzia

L’Oréal Paris Color Riche Shine Lipstick

While her makeup was typically pared back, a red lip made frequent appearances, adding just enough drama to her otherwise neutral palette. This glossy formula delivers that modern take on a classic crimson, the perfect finishing touch to a minimal ensemble.

$13.6 on Amazon (was $14.99)

Tyra Mini Dress

Carolyn also embraced romantic touches–case in point, the paparazzi shot of her in a quiet-luxury mini floral Chanel by Karl Lagerfeld from the 1996 Cruise collection. This airy mini nods to that softer side while keeping clean lines.

$288 at Reformation

You may also like:

Kitsch Satin Scrunchies – $8.79

Burt’s Bees Moisturizing Lip Balm – $11.86

Travel Jewellery Box Organizer – $12.99