Carolyn Bessette Kennedy and Jane Birkin Agree: These Are Jeans Are Actually The Chicest

Despite denim trends seeming par for the course, it’s often the case that when you find a jeans style that you like, you tend to stick with it. So, when it comes to the preferences of the world’s chicest women, you’ll find them staunchly loyal to only one style —bootcut jeans.

Look at a photo of someone like Bella Hadid, Carolyn Bessette Kennedy or Jane Birkin, and you’ll realise that despite their differing style philosophies, they share an affinity for this effortlessly elevated and slightly flared style. Why? It’s breezy, subtly bohemian and brings great structure to any ensemble.

Originating as a practical pair of trousers for rambling ranch hands and cowboys to toil around in—the name derives from the silhouette’s signature shape, which allowed them to slip in and out of with ease whilst keeping their work boots firmly planted on—bootcut jeans have since outgrown the rodeo and become a well-earned staple in any well-established wardrobe.

Once relegated to bucolic farmlands and mountainous landscapes to explore on horseback, the casualness and freedom of the Summer of Love sent them mainstream, with bootcuts cropping up in major cities and, surprisingly, without a trusty steed nearby. If you fast-forward a few decades from the ‘70s, they became a sigil of modern minimalism, with the practical nature and snug fit essential for those looking to achieve the sleek, sensual and utilitarian appearance that the ‘90s had promised.

In the noughties, things turned south, with bootcuts worn as bumsters and inches sliced off the waistband to create a low-rise effect. Now, however, it appears that those with taste have taken an “anything goes” approach to style the trend, plucking whatever attribute they like from ghosts of bootcut pasts to wear them in a way that feels fresh.

“Bootcut jeans perfectly blend nostalgia with contemporary styling,” explains Paige Adams-Geller, the owner and creative director of her self-titled ready-to-wear brand PAIGE. “Bootcut jeans are the ultimate balance between skinny and baggy jeans,” she adds. “They offer shape whilst still being comfortable and add a unique touch with the flared bottoms.” Though deeply tied to the past, Adams-Geller adds that the revival of bootcut jeans and regular celebrity sightings comes down to a desire to “reimagine the classic style for [today’s] wardrobe”.

The message is clear: Regardless of how you wear them, the important thing is that they’re worn. So, when it comes to making like these incredibly chic women, where does one start?

Whether you’re looking to expand your denim arsenal or re-up your favourite pair of trousers, I took to the streets to uncover once and for all what the best bootcut jeans are. From beloved designer brands like Agolde to high-street favourites from Mango, uncover the best bootcut jeans, as tried and tested by a fashion editor, ahead.

The Best Tk Bootcut Jeans of 2026:

• The Best Overall Pair of Bootcut Jeans: Mango Fiona Flared Mid-Rise Jeans, £36
• The Best Low-Rise Pair of Bootcut Jeans: Frame The Rodeo Bootcut Stretch-Denim Jeans, £310
• The Best High-Rise Pair of Bootcut Jeans: Paige Laurel Canyon High-Rise Stretch, £280
• The Best Designer Pair of Bootcut Jeans: Celine Bootcut Jeans, £790
• The Best High-Street Pair of Bootcut Jeans: H&M Bootcut High Jeans, £25

1. Mango Fiona Flared Mid-Rise Jeans

Style Notes: Like everyone with access to the internet, I have been absolutely besotted with Carolyn Bessette Kennedy’s wardrobe in Love Story. And whilst her outfits during her relationship with John F. Kennedy Jr. have long been chronicled, I found her workwear ensembles during her time as a senior publicist for Calvin Klein to be the most intriguing. Classic, considered and yet still contemporary, I’d contend that these Fiona jeans from Mango feature all the same hallmarks.

A mid-rise fit, this pair fits quite tight through the thigh before gradually widening from the ankle, resulting in the perfect hourglass shape down the leg. The wash is also quite in keeping with the ‘90s minimalistic aesthetic I was hoping to emulate when trying them on, as the light, baby blue added a softness and effortless elegance that feels fitting for a decade focused on quality, fabrication and silhouette.

But, the style wasn’t as clinical as you might expect, with the intentionally raw hem designed to provide a distressed element to an otherwise clean-cut shape. I took a size 10 here, which was great for that body-conscious shape that was all the rage back then, but for a bit more comfort, I suggest sizing up, as it can run slightly on the smaller size.

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2. Free People Double Knot High-Rise Straight Bootcut Jeans

Style Notes: Whether you’re a Sloan Ranger or have caught Western Fever, if there’s a bootcut jean in sight, you can count on a horse girl trailing close behind. Free People’s Double Knot high-rise straight bootcut jeans are certainly inspired by the latter, with the dark indigo wash and kick-out hem something you’d find in Beth Dutton’s wardrobe from Yellowstone or Bella Hadid’s rodeo-ready ensembles.

I, for one, am not someone who subscribes to the cowgirl aesthetic outside of wearing a raffia hat on a beachy holiday or a Harry Styles concert, so I was slightly dubious about how they would fare. However, after slipping into them, I was immediately convinced that these may as well be some of the best bootcut jeans I’d ever wear.

They sat high up around the waist and fell just below my ankle, meaning that they slightly dragged along the floor behind me, even in heels. However, I didn’t necessarily have an issue with that because they gathered really beautifully around my boots, injecting my look with a lived-in and authentic slant that would be hard to replicate without spending years on a ranch.

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3. H&M Bootcut High Jeans

Style Notes: As a high-street giant, it’s not uncommon for H&M to fill a niche gap in my wardrobe with a precise style I didn’t even know existed. These bootcut jeans solved several styling conundrums for me.

First of all, I was looking for a pair that didn’t flare so obviously around my ankle, as I’ve found that most styles can sit super wide and end up looking slightly trapezoidal on me. Secondly, I wanted a pair that would suit an array of shoe options, given I pretty much exclusively wear bootcut jeans with, well, boots.

As you can see, this pair only moderately expands around my foot and falls gently above the floor, meaning that I can pair both trainers, ballet flats and flip-flops (à la Jonathan Bailey and Alexander Skarsgård) with them. A versatile pair of denim that costs less than a cocktail at an East London bar or West London café? Sign me up.

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4. Agolde Kick Boot Flared Stretch-Denim Jeans

Style Notes: As a fashion writer, I have the rare privilege of playing dress up as a part of my job. A few months ago, I had the opportunity to test and review several of Agolde’s best-selling styles. In part, to see what all the fuss was about, but also to honestly vouch to you, our readers, that any recommendation does live up to its standard.

Through that assignment, I became quite familiar with the celebrity-adored brand and got to know what to expect from its designs—high quality, a rigid structure, a buttery feel and a style that factors in sustainable practices. You’ll find all these qualities in this pair. Honestly, there’s not much to elaborate on, given how superb every factor was, from the comfort level to the precise fit.

In saying that, one thing I did have a slight qualm with just came down to how the jeans were cut. Instead of the seam running straight down the inside of my leg, it curved out ever so faintly, making the joining incredibly visible as you walk. Now, this is only a small detail that someone who has made a career out of appraising and appreciating clothing would note, but I do want to note it as it’s really the only thing that stood out to me as being slightly adverse in an otherwise favourable pair.

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5. Zara Bootcut Mid-Waist Jeans

Style Notes: As someone who grew up on the coast, there’s something about summer denim that is so nostalgic to me. What does this mean, I can hear you ask. Well, allow me to explain. Summer denim is a subcategory that refers to balmy, languid and slouchy cuts designed to be worn in a variety of warm weather conditions, from by the sand at your favourite beach to cocktails at a rooftop bar overlooking the sea.

These bootcut jeans from Zara ticked every box for me, with the slightly wide-leg finish and sliced knee making this something you’d easily find in Marisa Cooper’s wardrobe from The O.C. They were slightly a bit lower around the waistline than described, but when with this cobalt blue tank and heeled flip-flops, they proved that bootcut jeans not only need be worn in the depths of winter when looking to combat the chill.

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6. Celine Bootcut Jeans

Style Notes: Ask anyone who is a devoted listener of After Work Drinks—a quasi-pop culture podcast hosted by former magazine editors Isabelle Truman and Grace O’Neill—and they’ll tell you just how much airtime is given to finding the perfect pair of jeans. Not just any ol style of denim, bootcut jeans in particular. After hearing them wax lyrical about this exact designer style many moons ago, I knew that I’d have to try them on myself to see what all the fuss was about.

Immediately, upon wearing them, I was completely besotted with the style. Like anything the French do, these jeans don’t come easy, as they’re made of a firm denim that offers little stretch. However, the process of owning a pair of jeans is breaking them in and having them mould to your natural contours, so if sizing is an issue and you’re after a looser fit from the outset, I’d recommend sizing up. What’s more, they boast that enviable bum-hugging-and-lifting je ne sais quoi that every pair of Pairisan jeans contains. After putting them on, I felt that my legs felt smoother and my behind looked more toned. (Sagginess doesn’t even enter Celine’s vocabulary!)

The wash was slightly distressed, and the cut cropped right at my ankle, making them a true Goldilocks pair for what I was after—truly just right. They are the most expensive pair of jeans I tried on, and whilst I’m not in the position to be dropping close to a thousand pounds on denim, if that works for you, I highly implore you to give this pair a chance. You’ll thank us for it.

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7. Frame The Rodeo Bootcut Stretch-Denim Jeans

Style Notes: In case you need proof of just how circular trends truly can be, here’s me recommending a pair of low-rise, slightly flared jeans in 2026. Indeed, these might’ve been all the rage 20 years ago, but with Y2K primed for another comeback, I can’t see a world in which these aren’t sought-after.

I’m not someone who ever wears jeans that sit below my belly button, but I wasn’t entirely put off, simply because of the reputation that precedes t the brand. You see, when you have fans that include Kendall Jenner and Sienna Miller, you know you’re in for something good. And that’s what I got with this style. Comfortable, slouchy but still quite structured, this is a style that suits both going out looks and errand runs. From farmer’s markets to cocktail bars, I can easily see this style complementing any setting it’s in. Just be sure to wear a slightly bigger heel as these jeans do feature quite a long leg. (Tall girls, this one is for you!)

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8. Citizens of Humanity Lilah High-Rise Stretch-Denim Blend Jeans

Style Notes: After reviewing more than a handful of bootcut jeans, I came to the conclusion that the best pairs are the styles that don’t deviate from a traditional silhouette. It’s true, without superfluous details, an excess of accents or anything too flashy, these Citizens of Humanity Lilah jeans certainly promise what they say on the tin. Delivering a pair of exceptional quality denim with a slim fit, hidden zip and slightly whiskering through the leg, I can easily see this pair becoming a go-to style in no time.

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9. Paige Laurel Canyon High-Rise Stretch

Style Notes: With a second-skin finish and slightly exaggerated silhouette, these Paige jeans honestly feel more like a flared legging than anything else. They’re not—they’re definitely a pair of denim—but they truly just fit so comfortably it’s really hard to believe that you’re wearing jeans.

Named after the area of the Hollywood Hills, this silhouette also feels the most vintage-inspired to me, which is perfect for those who are after that ‘70s shape pioneered by someone like Stevie Nicks or immortalised on screen by Riley Keough in Daisy Jones & The Six. I would caveat that these jeans are long, like incredibly long. So, make note that you’ll have to take them to a tailor to adjust them to your proportions or wear extra-high boots with them like the platform styles of David Bowie’s Ziggy Stardust era. Either way, if it's hedonism and SoCal ease you’re after, these deliver in spades.

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How We Tested

Who What Wear UK's SEO Writer, Ava Gilchrist, rigorously tested the best bootcut jeans over the course of a few months. This process began with looking at sales data and viral styles to determine which popular pieces were worth vetting in the first place, in order to see if they would live up to the hype. She also raided her own wardrobe, as any style that finds its way into a fashion editor's wardrobe is one that has already earned a sought-after stamp of approval. From this, she shortlisted styles and road-tested them for several weeks to see how easily they were to move in and how comfortable to live in. Then, we narrowed this wider selection down to just a handful that wholeheartedly vouch for and recommend.

Why Trust Us

At Who What Wear UK, fashion is our speciality. Our editors have years of industry experience, from reporting on seasonal fashion trends seen at international fashion weeks to working with some of the most recognisable names in fashion. Every item we recommend is carefully selected based on current trends, quality and real-world wearability.

We regularly try on pieces ourselves—everything from best-selling jeans to designer shoes—and speak to external experts and fashion insiders, staying closely connected to what our readers are searching for. Our advice is grounded in expertise, and each and every buy we feature has to meet our exceptional taste standards—so you can feel confident in every recommendation.