From Calvin Klein to Prada—Everything Im Buying in 2026 to Look Like 90s CBK

I’ve been in love with this collarless blazer since it debuted on the runway. Though the shape is a bit boxier than what Bessette preferred in the ’90s, I think she would have loved the interesting shape.

This cashmere-silk sleeveless knit is a dream, whether you pair it with a pencil skirt like it’s styled above or with Bessette’s favorite jeans, Levi’s 517s.

These jeans have a similar look with subtle flaring at the bottom, but they have a lower waist, which is becoming more and more popular in 2026.

I can’t stop thinking about these perfect Jimmy Choo leopard-print loafers. They remind me of Bessette’s iconic snakeskin heeled loafers by Prada and are perfect with jeans and a sweater.

For a chilly morning at the Cape, I can totally see modern-day Bessette wearing this maxi cardigan coat by Lisa Yang with jeans and flip-flops.

Duh. It’s literally called the Bessette Headband.

This dress is so Carolyn Bessette coded, both IRL and in the show, Love Story. The real Bessette wore one like it with long velvet opera gloves, but in the show, Sarah Pidgeon donned the Calvin Klein strapless frock more simply. I can actually see her wearing it with this jacket and these loafers as well for a more dressed-down, day-after look.

Since I already own and love the reissued version of Bessette’s favorite Prada from 1995, I thought I’d look into another shoulder bag that feels like her. I adore the kiss-lock closure on this Jil Sander alternative.

Skirts were an area where Bessette had a bit of fun, so I feel like she’d be very into this chocolate-brown velvet column skirt from Blazé Milano. The texture and color create such a rich piece.

Bessette rarely wore jewelry, but when she did, it was usually just a simple pair of pearl studs.

A classic, elegant tank top to style with jeans, skirts, and more.

I think Bessette would have loved High Sport. Its pants are so easy to toss on and look sophisticated in.

A classic choice that makes every outfit better.

This satin pencil skirt would have gotten so much wear at the Calvin Klein office.

A simple turtleneck in the front, a daring statement in the back.

Though she loved her classic blue 517s, Bessette wasn’t afraid to venture out into other denim options, like khaki and brown jeans.

Jamie Haller’s loafers are beloved by fashion people everywhere for their sleek look and ultra-comfortable fit.

The blue lenses are a stretch, but I think modern-day Bessette would be down to try them.

I mean, I had to include this incredible Nour Hammour coat in leopard-print pony hair.

Another piece of jewelry Bessette made an exception for: Cartier’s Tank watch.

Everyone thinks of Carolyn Bessette’s city style, but her laid-back looks at the beach were just as chic.

We usually saw Bessette carrying a black bag, but I think she would have loved this cognac Prada tote, at least once she beat it up a little.

Pearls were her thing, clearly.

The elegance! I can’t stand it.

I get the feeling that these would have been heavy in Bessette’s 2026 rotation—just like they will be in mine.

Perfect for tucking into skirts and jeans.

Maybe this is a stretch, but I think the cool texture of this skirt would have called out to Bessette, especially in her younger years.