How to Channel Carolyn Bessette-Kennedy’s Iconic ‘90s Looks for Fall

Bottoms

When picking trousers, I don't think CBK would fall victim to a barrel jean; instead, she'd pick up a tailored slack like the Drew Pant from Tanya Taylor.

For everyday-wear, I could see Carolyn Bessette-Kennedy shopping at Lilysilk for a pair of Full Bias Cut Silk pants. The comfy, silky texture can be dressed up or down and elevates any look.

If she were planning to go to an event right after work, CBK might wear some version of her iconic long skirt and white button-down look. To recreate the outfit, I would invest in Lilysilk’s flare hem Silk Maxi Skirt (its flared cut is flattering on anyone).

Jackets 

Not only was CBK a fashion icon, she was also a successful business woman. Her career began at Calvin Klein where she worked her way up from sales assistant to director of publicity and show production for the flagship store. She would eventually go on to direct the spring and fall shows for the brand. As a career woman, CBK would surely need a good blazer like the Single-Button Silk-Wool Blend Blazer from Lilysilk — versatile enough to wear to the office, out to dinner and even transition into spring with a tailored short.

A lover of long overcoats and trenches, Carolyn Bessette-Kennedy was frequently pictured wrapped up in an oversized style. A perfect trench is a necessity, and the Rockaway Trench from Buck Mason will have you feeling sexy and comfortable at every turn.

CBK loved her vintage faux-leopard overcoat in the ‘90s, there are plenty of pictures online of her wearing it to stroll the park with JFK Jr. The coat became so iconic the original sold at a Sotheby’s auction for an estimated $20,000-$30,000. To get the look, try Rixo’s Milly Leopard-Print Faux Fur Coat to top off a neutral outfit.

Out on the Town

CBK wasn’t afraid to put on a dress to tackle a busy day. And some of her most iconic day-to-night outfits feature mini- or midi- dresses with a long coat draped over top, giving an effortless vibe to the look. One of my favorite silhouettes right now, and something I’m sure a ‘90s star like CBK would love, is Leset’s Barb Lace V-Neck Mini Dress. The mini-slip is made from a  gorgeous silk material and features lace at the neckline to elevate it. 

Another great choice for a LBD, Lilysilk’s V-Neck Silk Long Dress grazes the body beautifully without hugging too tightly. Lilysilk’s namesake fabric is divine and would pair perfectly with a black kitten heel. I could also see CBK wearing The Favorite Linen Black Dress from Favorite Daughter. She paired a similar dress with long, black opera gloves, but in 2025 a classic updo and a heeled sandal will do just fine.

Strutting in Style

If CBK was going to rebuild her shoes lineup in 2025, she would start with a pair of ballet flats from Margaux NY. The Demi silhouette is my ride-or-die if I need to walk long distances. The dreamy, Nappa leather molds to your foot and the adjustable tie lets you find your perfect fit without sacrificing the classic ballet flat look.

For a modern take on the flat, CBK might try The Una flat from M.Gemi, and for loafers, I’d recommend these Elba Loafers from female-founded brand Frēda Salvador (by the far the most comfortable pair I've ever worn).

And because this wouldn’t be a CBK roundup without a tall boot: I love a pointy toe seen on styles like the Auggie Boot from Dolce Vita. If you need something a little fancier than a boot, Birdies makes the most versatile pointy kitten heel on the market right now.