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The CBK Wardrobe, Simplified
Carolyn Bessette-Kennedy? She’s everywhere right now, due in no small part to the buzz surrounding FX’s “Love Story” TV series that has once again thrust her passionate and caustic relationship with Kennedy heir JFK Jr. into the spotlight. As each new episode of the viral show drops (on Thursdays at 9 p.m. EST; you can tune in thanks to our handy streaming guide), fashionistas everywhere go wild for CBK’s sartorial equations portrayed on-screen by Sarah Pidgeon — be it slinky LBDs, camel-hued pencil skirts, minimalist cashmere sweaters, or tailored, longline coats perfect for transitional-weather dressing.
The conversation is both positive and negative, with some sharp-eyed critics noting that the show could’ve done a better job at sourcing pieces from actual designers worn by its heroine — from Yohji Yamamoto to Issey Miyake. It’s a well-known fact, though, that renowned costume designer Rudy Mance stepped in to helm the department at the eleventh hour and has done much to course-correct the original designer’s quite unrepresentative wardrobe decisions on “Love Story.”
For the most part, viewers are swooning over Bessette-Kennedy’s effortlessness and all the ways in which she was able to become a beacon of ’90s style. Going hand in hand with culture’s latest obsession, there’s also been an uptick in purchases from labels like Ralph Lauren and Calvin Klein — worn on the regular by the legendary Calvin Klein publicist while she was out and about with “America’s Prince” in NYC. Other brands and attire in particular demand are the J.Crew 1988 Rollneck Sweater; the Wedgie Bootcut Jeans from Levi’s, a modern revival of Bessette-Kennedy’s beloved (yet discontinued in women’s sizing) 517 pair of choice; Manolo Blahnik’s Callasli 90 heels, which she often liked wearing with crisp button-ups and black maxi skirts; and the Selima Optique Aldo sunnies that she was wont to pairing with a tortoise-printed headband from C.O. Bigelow.
At the labels rounded up below, you have the best chance of finding the silhouettes CBK popularized to the point of them becoming synonymous with 1990s minimalism (if not the precise selections that took up residence in her closet). We’ll be highlighting multiple trending items from each, to help get you one step closer to acing Bessette-Kennedy’s “less is more,” neutrals-powered, and logo-averse aesthetic, right in time for spring.
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Ralph Lauren
Famously, CBK once wore a black Ralph Lauren turtleneck with Helmut Lang pants and a Hermès Birkin while walking down the street with her beau. Her personal style — clean, Americana, old-money — has always closely aligned with the fashion house’s design codes, so it’s no surprise that you can currently find no shortage of RL gems that feel like they’d be instantly embraced by the ‘90s golden girl.
From belted coats to sensible skirts and, of course, all-black long-sleeves for early spring, here’s everything to shop at the heritage outfitter for paying homage to the woman of the hour.
Ralph Lauren Silk-Blend Turtleneck Sweater
Though Bessette-Kennedy’s turtleneck was likely a 100-percent cashmere creation, this on-sale mulberry silk alternative would still check all of her boxes: being body-hugging, incredibly soft, and never loud as far as colorways go. While the brand does offer the style in shades like Ralph Red and Lavender Frost, it’s impossible to visualize them swathing CBK’s slender, 5′ 9″ frame. Brightness? Never.
Price upon publish date of this article: $94.99
Ralph Lauren Double-Breasted Wool Coat
Wool coats from Prada were an idée fixe for the leading lady, seeing as how she owned multiple types (always one of each in both black and camel). A single-breasted Prada coat she wore sold for $192,000 at auction recently, which goes to show that finding an exact match is… pretty unrealistic at this point. But here’s a close second from the CBK-approved Ralph Lauren — similarly camel-colored, crafted out of sumptuous Italian wool, and featuring prim-and-proper details like peak lapels and buttoned cuffs.
Price upon publish date of this article: $798
Ralph Lauren Double-Faced Satin Skirt
One of Bessette-Kennedy’s most famous photographs was taken on October 6, 1996, shortly after she tied the knot with John F. Kennedy, Jr. In it, she’s wearing brown boots, a pencil skirt, and a simple V-neck sweater: another example of how well the camel-black mashup works when done right. Though this satin number from Ralph Lauren hasn’t been sighted on the tastemaker, it’s a hybrid, almost, of her favored black slip dresses and more formal skirt styles that touched slightly below the knee. Skip its Newport Navy version and go straight for the black, savoring the item’s fluidity, positioning right at the natural waist, and go-with-everything versatility.
Price upon publish date of this article: $298
J.Crew
A sweater that debuted in J.Crew’s 1988 catalog is getting immense traction right now, almost four whole decades after its arrival on the scene, for one simple reason: “Love Story” actress Pidgeon, playing Bessette-Kennedy, donned it in Episode 5. Miraculously, the wardrobe staple is still available to shop from the brand’s menswear line, in the same shade chosen by the fictional CBK. And while we don’t have direct confirmation of the real style hero buying J.Crew, we had to include it in this roundup, what with J.Crew’s most popular buys — all to follow — being the epitome of ’90s minimalism and offering accessible ways to imitate Bessette-Kennedy’s fashion habits.
J.Crew Tortoise Headband
Bessette-Kennedy’s Charles J. Wahba headband is one of the most instantly recognizable (and only!) accessories the urbanite wore, and it’s still sold at circa-1838 pharmacy C.O. Bigelow Chemists in downtown New York. Since “Love Story” first aired, hundreds of content creators and everyday fashionistas rushed to grab the headband from its original source. If you don’t live in the city but still want to nail the look, turning to J.Crew might be your best bet. Unlike on C.O. Bigelow’s site, its tortoise headband is still very much in stock. Some perks? It’s been cut, shaped, and polished by hand in Lyon, France, which means every last detail here is bound to be just-right. “Treat it with care and it’ll last a lot longer than the drugstore variety,” J.Crew says in its marketing copy, perhaps cheekily referencing the whole CBK headband shopping saga.
Price upon publish date of this article: $29.50
J.Crew 1988 Rollneck Sweater in Cotton
This is the authentic, spotted-on-“Love Story” sweater from J.Crew that style editors can’t stop raving about, and, in the creamy Mountain White color, it clocks in at under $100. Want to go the extra mile? Personalize the late-winter nonnegotiable with a monogram, an option that also makes it a great gift for every devotee of Bessette-Kennedy’s quiet-luxury aesthetic. We can just imagine her putting it on alongside some lightly flared jeans and sneakers. (Yes, she was a fan of athleisure in the right circumstances, sometimes stepping out in Nike Air Streak trainers and baggy half-zips.)
Price upon publish date of this article: $98
J.Crew Featherweight Cashmere-Blend Cropped Sweater Shell
A simple white or black tank top: That’s all Bessette-Kennedy needed to look put-together in her signature, off-duty way. Some of her favorite brands in that department included Yohji Yamamoto, which she put into fluent conversation with Cartier (watches) and the previously referenced Levi’s (517 jeans). This right here is an opportunity to get the look without having to spend hours scouring eBay. J.Crew’s Featherweight Cashmere-Blend Cropped Sweater Shell is shrunken for easy layering with all the high-waisted pants in your rotation, composed of cashmere that promises to be “lighter than air,” and boasts attractive ribbing at the hem and neck for good measure.
Our generation’s next trendsetter? It just might be you.
Price upon publish date of this article: $158
Calvin Klein
Of course, Bessette-Kennedy’s closest association was with Calvin Klein, where she worked as a publicist after college and until 1996. Her career trajectory at the label was truly impressive, going from salesperson to director of publicity, in which capacity she dealt with Calvin Klein’s most high-profile clients. Over the years, she came to embody the brand and all of its pared-back allure (at the time, according to multiple reports, employees had to keep their makeup to a minimum, wear only a few pieces of jewelry to the office if any at all, and stick to very monochrome ensembles). There’s no doubt that this internal manifesto had a big influence on how CBK presented herself to the world, with Calvin Klein playing a major role in her life in more ways than one. Most importantly, she met her future husband JFK Jr. there in 1992, when the VIP client came in for a fitting.
The rest, as they say, is history.
Calvin Klein Lynn Midi Dress
Spaghetti strap–equipped slip dresses could often be seen on the style icon in question, either worn sans cover-up — with just black loafers and shades for companions — or under long black coats when the weather called for it. She was partial to styles that were on the looser side but never oversized, often outfitted in silk for some softness and breeziness. Calvin Klein’s Lynn Midi Dress is part of its fall 2025 collection but looks like something that arrived via time machine from the nineties: so slinky, sensual, and streamlined it is. Swapping silk for wool crepe de chine, the frock charms with a cowl neckline and exposed back. Bessette-Kennedy would feel at home in it: We just know it.
Price upon publish date of this article: $1,960
Calvin Klein Ishaya Sandal
Paparazzi photos of JFK Jr.’s wife in the warmer months are harder to find, meaning we are less familiar with Bessette-Kennedy’s footwear choices in the spring and summer. What is an established truth: her love of strappy, “naked” heels that didn’t overwhelm the larger outfit du jour. And though the ones she most frequently threw on (with a jeans-and-blazer combo or a jeans-and-black-tank combo) came courtesy of Prada, Calvin Klein’s iteration replicates the vibes immaculately. A two-inch heel, square toe, and buckle closure come together in a marriage of good looks and function. As a result, you’ll soon find yourself wearing your white sneakers less and your Ishaya Sandals more.
Price upon publish date of this article: $99
Calvin Klein High Rise Ankle Bootcut Jeans
Remember how we pointed out that the Levi’s Wedgie Bootcut Jeans are the closest real-time equivalents of the 517s CBK adored? Well, Calvin Klein comes in clutch with its own take that’s way more budget-friendly (under $50 as compared to Levi’s’ $110 price tag). The best news? The denim is stocked at Amazon and so can come to Prime members in just two days — in case you want to watch the next “Love Story” episode in a ‘fit Bessette-Kennedy would’ve complimented. The high-rise style flares out ever so slightly beyond the knee, bringing vintage-coded flair to even your most casual getups. Or, as she might’ve put it, effortless getups.
Price upon publish date of this article: $45.82
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Stacia Datskovska is a Senior Commerce Writer at WWD. Previously, she worked at ELLE DECOR as an assistant digital editor, covering all things luxury, culture, and lifestyle through a design lens. Her bylines over the past five years have appeared in USA Today, Baltimore Sun, Teen Vogue, Boston Globe, Food & Wine, and more. Prior to joining ELLE DECOR, Datskovska learned the ins and outs of e-commerce at Mashable, where she tested products, covered tentpole sales, and curated gift guide roundups. She graduated from NYU with a bachelor’s degree in journalism and international relations. Datskovska regularly reports on iconic celebrity style moments and how to replicate them in 2026.
