9 Capsule Wardrobe Staples Inspired by Carolyn Bessette-Kennedy

No matter how involved you are in modern-day fashion conversations, you’ve likely heard one style icon’s name brought up several times over the last few weeks: Carolyn Bessette-Kennedy. Famous to the masses because of her marriage to John F. Kennedy Jr. in the 1990s, she was (and still is) worshipped by fashion lovers for her immaculate sense of style. A publicist at Calvin Klein when ‘90s minimalism was at its peak, Bessette-Kennedy and her covetable wardrobe inspired feverish obsession with every new paparazzi shot released. 

Now, with Hulu’s buzziest new show, Love Story, showcasing the It girl’s relationship evolution with JFK Jr. before their tragic passing in 1999, Carolyn Bessette-Kennedy, or “CBK,” as she’s known in the zeitgeist, is on everyone’s minds more than ever, especially for many Gen Z fashion lovers who were too young to witness her style IRL. 

If you’re just as infatuated with CBK’s effortlessly chic style as I am and are suddenly wanting to shop with her minimalist approach in mind, look no further than Gap and J.Crew for capsule wardrobe essentials. From CBK-coded hair accessories to simple investment pieces that will actually last in your closet, here’s a curated collection of minimalist styles from Gap and J.Crew on par with Bessette-Kennedy’s taste. 

J.Crew Tortoise Headband

CBK was often seen with a tortoise hair accessory, famously from C.O. Bigelow apothecary in NYC. This similar style headband from J.Crew is equally chic and functional, elevating any simple outfit or improving any bad hair day. 

Gap High Rise ’90s Slim Straight Jeans

If there’s anything we know for sure about Bessette-Kennedy, it’s that even if she was wearing something casual like a pair of denim, she made it look expensive and effortless. These ‘90s-inspired straight-leg jeans with a slimmer fit have the same vibe, and look a tad more elevated than baggier styles.

J.Crew Cashmere High V-Neck Sweater

I’m a sucker for a simple, 100% cashmere sweater, especially this black one from J.Crew that I think CBK would wear on repeat. Its no-frills silhouette and V-neckline that’s easy to layer over white t-shirts is truly a wardrobe staple. If you want something more fun than plain black, this style comes in eight other colors. 

J.Crew Ballet-Sleeve Top In Lightweight Stretch Cotton Blend

Boatneck tops have always been chic—CBK emphasized this by sporting tops and dresses with this neckline on several occasions. I’m obsessed with this lightweight cotton option, especially in the ivory shade, and love how you can still wear a normal bra with it. 

Gap Flip-Flop Sandals

Though friends think I’m crazy for wearing flip-flops around New York City, I know it’s okay because Bessette-Kennedy did, too. She’s been frequently photographed wearing classic black flip-flops, similar to this pair from the Gap, which even has a slight platform for an added chic detail. 

J.Crew Western Straight Jean

If CBK wore baggier denim, it looked like this pair from J.Crew—relaxed, comfortable, but still effortlessly chic and with subtle shape. This style reminds me of my favorite vintage pairs, with the slightly wider leg, straight-leg design, and gorgeous classic blue wash.  

J.Crew New Perfect-Fit High-Neck Tank Top

Nothing pulls a look together like a perfect-fitting white tank top—this simple basic from J.Crew is very Carolyn-coded. The slimmer fit and higher neckline give it a more polished feel than other tanks, in my opinion. 

Gap Modern Square-Neck Maxi Dress

There are several famous paparazzi photos of CBK in a gorgeous, simple black dress, but one of my favorites is of her in a casual black slip dress, wearing nothing else but her famous oval-shaped sunnies and heeled loafers. Though this Gap option is a maxi and not a midi dress as she has on in that photo, it has the same chic, effortless vibe, with a simple square neck and body-skimming fit. 

J.Crew Étienne Oversized Shirt In Lightweight Oxford

If you don’t already have a plain white button-down in your closet, here’s your sign to invest in a high-quality option from J.Crew. Dress it up with a long wool skirt (like Bessette-Kennedy famously did at Calvin Klein) or casually with denim.