Carolyn Bessette-Kennedy Inspires the Best Bootcut Jeans for Spring 2026

Finding the right pair of jeans is the kind of wardrobe problem that sounds small until it isn't. The silhouette either works or it doesn't, and the bootcut, for all its quiet confidence, demands conviction. Right now, that conviction comes with a very specific reference point: Carolyn Bessette-Kennedy, the '90s publicist and perennial style reference, has quietly reclaimed her place on fashion feeds, sparked by the TV show centered around her relationship with John F. Kennedy Jr. in *Love Story*. The effect on denim in particular has been immediate and total.

Frequently photographed in Levi's bootcut jeans, particularly the 517s, a style originally designed for men, Bessette-Kennedy made the silhouette entirely her own, turning practical denim into something undeniably refined. She often paired her Levi's 517 bootcut jeans with boots, heels, belted coats, tees, turtlenecks, and crisp white button-downs for a casually sophisticated look that embodied her low-maintenance aesthetic. The formula hasn't aged a day.

As Natasha Halesworth, founder of The Consistency Project, a New York-based shop that sells vintage and deadstock denim, explains: "Many confuse a bootcut with a traditional vintage flare; however, they are very different and not actually as wide. It's a classic straight-leg jean that can accommodate a boot, so there is a subtle, wider opening at the base of the leg." That distinction matters when you're shopping, because the wrong pair tips into costume territory. The right pair just looks like you got dressed well.

The silhouette is on the up-and-up, with It girls like Bella Hadid and Anne Hathaway recently sporting the trend. After years dominated by exaggerated proportions and overtly nostalgic denim trends, the bootcut reads polished, balanced, and quietly confident: the kind of jean that slips seamlessly between tailoring, heels, and ballet flats. Here, ranked by wearability and CBK-credibility, are the best bootcut jeans for spring 2026.

1. Levi's 517 (The Original Reference)

Carolyn Bessette-Kennedy's minimalist '90s style, including her go-to Levi's 517 bootcut jeans, is experiencing a resurgence in popularity thanks to *Love Story*. The exact same Levi's 517 jeans that Bessette-Kennedy favored can still be purchased today for $75 or less, making them an affordable way to channel her effortlessly chic aesthetic. Originally designed for men, the 517 sits clean through the hip with a subtle kick flare: understated, elongating, and unmistakably '90s. It's the referential starting point for everything else on this list.

2. Levi's Wedgie Bootcut Jeans

Bessette-Kennedy's ride-or-die style of choice was the Levi's 517, a classic high-rise bootcut silhouette that slimmed the leg while leaving the perfect amount of flare for those '90s boots. Levi's no longer carries a women's fit for the 517, but the closest option is the Wedgie Bootcut. Fashion experts note the bootcut silhouette, unlike a true flare, has a subtle wider opening at the base of the leg to fit over boots, creating a feminine and almost-sexy look that the Wedgie delivers in spades. The hip-hugging fit is a reliable fan-favorite for good reason.

3. Levi's 725 High-Rise Bootcut Jeans

The 725 is the contemporary Levi's option with the most editorial currency right now. A modern reinterpretation of the 517, this Levi's captures the same vintage attitude; a slightly higher rise and sculpting through the waist give it that polished, off-duty model energy CBK perfected. Glamour featured it as a key piece in their CBK-inspired spring capsule, pairing it with a Gap Modern Crewneck Tank Top, strappy sandals from Madewell, and a dainty bracelet watch for a spring-summer ensemble they noted still looks fresh thirty years after CBK first wore the look.

4. Rag & Bone (Designer Denim)

When the occasion calls for an upgrade, rag & bone is the name to know. The brand's bootcut offerings bring a precision of construction that separates them from the high-street pack: a cleaner inseam, denser fabric weight, and a cut that doesn't require breaking in. As Marie Claire put it plainly, "as far as designer denim goes, rag & bone makes some of the best." The investment is worth it when the pair earns rotation across seasons.

5. Good American Bootcut Jeans

With a narrower waist and extra room at the hips and thighs, Good American jeans fit hourglass body shapes like a dream. The brand's reputation for inclusive sizing and stretch-forward construction makes this the most accessible entry point for the silhouette. A stretchy construction means the pair is ultra-comfortable, which, as Marie Claire notes, is genuinely a feat for jeans.

6. Gap Bootcut (The It-Girl Everyday Option)

Gap's bootcut has earned its own kind of cult status this season. Marie Claire's writer described throwing on her Gap pair and feeling "like an It girl the second I throw them on," which is exactly the register this silhouette operates in when it's done right. The brand's signature "Magic Pockets" on select styles deliver a supportive, hold-you-in feel without the stiffness that plagues cheaper denim. For an everyday in-between wash that handles everything from errands to dinner, Gap is the pragmatic choice.

7. Madewell Bootcut (Split-Hem and Cropped Styles)

Madewell's denim credibility is well-established, and their bootcut and flared-hem offerings for spring 2026 speak directly to the CBK reference. The cropped raw hem just feels right for the warmer weather, and CBK particularly loved a cropped hem, so the detail carries real archival weight. Madewell denim is an editor-favorite for many reasons: pricing is constant and affordable, with many options under $150, and sizing is inclusive, with curvy, petite, short, and tall options available. A split-hem version works especially well for showing off a strappy sandal or pointed-toe mule.

8. Low-Rise Bootcut (The Y2K Lean)

For those willing to push the silhouette into early-2000s territory, a low-rise bootcut offers a deliberate nod to the moment just after CBK's peak. Y2K low-rise jeans styles still reign in 2026, and the silhouette pairs well with bootcuts and flares in addition to baggier options. An extra-low rise reads as a confident, specific aesthetic choice rather than a throwback accident, particularly when kept minimal on top with a tucked tank or simple crewneck.

9. Black-Wash Bootcut

Solid black jeans are great for spring work outfits, and a black-wash bootcut is the sharpest, most versatile iteration of the trend. The silhouette immediately reads more polished in a dark or black wash, functioning as dressed-up denim that works from a business-casual context straight into evening. CBK was, after all, an evangelist of wearing black absolutely everywhere, so a black bootcut is perhaps the most faithful homage of all.

10. More-Flared Leg / Boho-Leaning Bootcut

Not every pair needs to toe the minimalist line. A bootcut with slightly more flare at the hem moves toward '70s territory and brings a more relaxed, boho energy that suits spring dressing. What once felt like a strict throwback has become a nonstop reach: that subtle flare balances everything out, especially with chunkier shoes or boots. For those looking to lean into the silhouette rather than whisper it, this is the version that makes the biggest visual statement while staying grounded in the same foundational geometry.

How to Style Them

The CBK formula is disarmingly simple. Style bootcuts with classic boots or a pair of chic loafers, as seen on Bessette-Kennedy, or even a set of heels to dress them up a touch. Glamour's recommended capsule build for the tank-top-and-bootcut outfit centers on a high-neck tank, a bracelet watch, and strappy sandals, noting it's "a spring-summer ensemble that still looks fresh 30 years later." For a more layered look, a topcoat thrown over a simple T-shirt and the jeans replicates one of CBK's most-photographed off-duty looks.

Practically a masterclass in curating a capsule wardrobe, her looks were marked by clean lines, sophisticated neutrals, and of-the-decade accessories. The bootcut jean is the anchor. Everything else, from the wide headband to the Le Specs oval frames to the Evita Peroni tortoiseshell, follows its lead. Its return feels less like a revival and more like a reminder that the strongest wardrobes are often built on the simplest foundations.