6 Shoe Styles That Make Bootcut Jeans Feel Chic and Modern, Instead of Stuck In 2005

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).

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.)

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.

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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.

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3. Pointed-Toe Mules

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.

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4. Heeled Flip-Flops

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.)

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5. Loafers

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.

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6. Low-Profile Trainers

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…

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