While the very nature and name of this viral denim style might indicate that the best shoes to wear with bootcut jeans be the footwear shape featured in its moniker, let me be the first to admit that this cut is actually misleading. That’s not to say that boots aren’t a suitable pairing for bootcut jeans. On the contrary, this fit is so harmonious that the entire denim category is titled after it. However, I feel that this epithet can be considerably deceptive and trick people into believing that boots are the only thing that works with them. Quite the opposite is true, in fact.
The fit-and-flare structure of bootcut jeans is already something that makes them such a hero in any well-edited wardrobe. But this slight broadening from the knee to ankle is also what makes them versatile enough to work with an array of shoe styles, going beyond the humble kitten-heel knee-high (Saint Laurent’s slinky Francoise) or square-toe contemporary classic (Khaite’s Nevada).
(Image credit: Getty Images)
Christian Dior once said, “You can never take too much care over the choice of your shoes”, which is an apt adage I’m committing to heart when it comes to bootcut jeans and shoe pairings. You see, the slightly frustrating part about wearing bootcut jeans with the wrong shoe, per se, is that you might end up looking like Marissa Cooper from The O.C.
While Mischa Barton’s character is so beloved with her arsenal of Chanel handbags and coterie of flouncy boho dresses, one wrong step and you could be wearing an ensemble that feels slightly like it’s stuck in 2005. Of course, with the Y2K renaissance still in progress, this isn’t necessarily an issue. Still, there are certain shoes that help bootcut jeans feel more contemporary and chic. (And fitting for 2025.)
(Image credit: Everett Collection)
Interestingly, bootcut jeans have also emerged from the slumber of early 2000s fashion trends and are swiftly becoming one of the most in-demand silhouettes for the autumn/winter period. No longer slung low on our hips and paired with shearling-lined Uggs, the bootcut jeans of now are modern, polished and a little flirty—so shouldn’t the shoes we wear with them reflect this mode?
So, whether you’re looking for a little lengthening or more effortless pieces that lean into the languid tones of yore, it truly is becoming more imperative than ever to know the best shoes to wear with bootcut jeans. Without further ado, scroll on below for the pre-eminent styles that will make your denim outfits feel far fresher this season.
The 6 Best Shoes to Wear With Bootcut Jeans
1. Ankle Boots
Style Notes: Obvious? Yes. Derivative? Never. Putting the boots in bootcut jeans, it would be remiss of me to begin this edit without calling out the shoe style this denim is actually inspired by. Unlike straight-leg or super skinny jeans, bootcuts are designed to be spacious enough to accommodate any length, however, I particularly enjoy wearing them with ankle-grazing styles. There’s almost something tantalising about the way only you know that the end of your shoe just kisses the bottom of your leg while the rest of the world thinks you’re polished and put together enough to wear something that could even extend above your calf.
Shop the Shoe:
MANGO
Pointed Heel Ankle Boot
Inspired by the quite minimalism of Toteme, these razor-sharp Mango style will have you feeling your best stealth wealth self.
Brown suede and blue bootcut jeans might’ve been a hallmark of the ’70s, but thanks to brands like Rixo and Valentino, the look is certainly chic again.
KHAITE
Nevada Suede Ankle Boots
The sock-like finish and contrasting toe accent has made this Khaite pair truly the standout of the season.
2. Ballet Flats
Style Notes: While those with a stronger moral backbone might always take the high road, the same can’t be said for the sophisticated dressers wearing bootcut jeans. A heel never goes astray at the best of times, but I can’t in good conscience omit all the flat options that look equally good. Ballet flats might seem like an unruly combination, but the mixture of an ultra-prim and feminine shoe with a relaxed and masculine trouser achieves that chic décontracté (or casual chic, for those of us who don’t speak French) that Parisians are internationally revered for.
Shop the Shoe:
COS
Suede Heeled Ballerinas
I personally love a ballet bump, and if the virality of styles from Dear Frances and Repetto are testament to anything, I’m in the majority here.
ZARA
Satin Ballet Flats With Bow
Rounded satin styles might’ve reigned supreme after debuting on Miu Miu’s autumn/winter 2025 runway, but pointe-inspired square toes truly are the next iteration of the trend.
GANNI
Leather-Trimmed Canvas-Jacquard Ballet Flats
For those with an aversion to the girlishness of ballet flats, allow me to direct you to this more eclectic Ganni style. With a cloth exterior that reminds me of a 17th Century French tapestry and a belt strap reminiscent of the artwork of Tom of Finland, this truly is the most avant-garde style I’ve come across.
3. Pointed-Toe Mules
(Image credit: @sylviemus_)
Style Notes: Though I hate to sound fickle after waxing lyrical about going sans heels in your next bootcut jeans outfit, consider this effortlessly elegant outfit from French girl muse Sylvie Mus as a testament to the merits a slightly elevated shoe can bring. Timeless for a reason, the pointed toe and backless shape bring a soft tailored effect that enhances even the most elementary looks.
Shop the Shoe:
ZARA
Mule Slingback Shoes
Gucci
Women’s Mule With Horsebit
This Gucci pair has gone to the top of my wishlist.
Topshop
Ivette Croc Patent Close Toe Mule in Black
The amount of time the Olsen Twins have stepped out wearing croc-effect heels and bootcut jeans almost feels immeasurable, so you know this is a chic fail-safe combination you can rely on.
4. Heeled Flip-Flops
(Image credit: @salome.mory)
Style Notes: One to bank for hotter temperatures, but I can’t think of a slinkier look than combining a sensual heeled flip-flop with a bootcut jean. Throw on a white button-down shirt that’s knotted at your belly button for a look that will have you channelling Jane Birkin in her prime. (Because who doesn’t want to feel like they’ve just returned from a sojourn in Saint-Tropez.)
Shop the Shoe:
Alaïa
Velvet Thong Sandals
Talk about a head turner! This padded Alaïa pair has begun cropping up in the wardrobes of so many refined dressers—Devon Lee Carlson, Kylie Jenner, you know the drill—and I really can’t think of a cooler style to invest in next.
Toteme – INT
Croco-Embossed Heeled Flip Flops Black
Steve Madden
Tracie-J Sandal Smoke
A chic continuation of the jelly sandal trend that reigned supreme all summer.
5. Loafers
(Image credit: @nlmarilyn)
Style Notes: It feels counterintuitive to call loafers a trending item, considering they were invented nearly a century ago. In that time, though, it feels like they’ve traded up from the floors of Wall Street and corporate attire to become a cool girl staple endorsed by the likes of Zoë Kravitz and Kendall Jenner. Indeed, there are really no limitations when it comes to what you can team loafers with, and I personally find the pairing of a floor-skimming bootcut jean and a moccasin-esque pair particularly tasteful.
Shop the Shoe:
6. Low-Profile Trainers
(Image credit: @fakerstrom)
Style Notes: Jeans innately lend themselves to a more undone disposition, so why not embrace those qualities by opting for a pair of trainers? When you know you can walk upwards of 10,000 steps comfortably and still look like you’ve just stepped off of Celine’s runway, I can’t think of a reason not to try them. The only caveat is to avoid anything too chunky. Sticking to retro styles and low profiles will help bring cleaner lines to a look that can otherwise veer on the boxy side. Dries Van Noten, COS and Zara are doing this shape exceptionally well at the moment, proving to be the true definition of putting your best foot forward…
Shop the Shoe:
COS
Minimal Leather Trainers
Whenever I coveting a stranger’s outfit while out and about in London, nine times out of ten they’re wearing this style.
ZARA
Contrast Running Sneakers
Khaki is one of the biggest colour trends of 2025, and this nylon and suede style feels like a particularly apt way to inject the trend into your outfits.
DRIES VAN NOTEN
Leather-Trimmed Shell Sneakers
The Dries pair that won’t stop haunting me…
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