Bootcut Leggings Can Look Strange With the Wrong Shoes, But These 5 Styles Look Chic

To even utter the word leggings is to be confronted with a barrage of thoughts on whether the casual trouser style is appropriate or not. But irrespective of your own personal opinions on them, there’s no denying that they’re certainly in fashion. This season, however, one of the biggest leggings trends to emerge is the return of bootcut leggings.

Despite being someone who grew up in the early 2000s, I’m slightly dissuaded by the shape’s comeback simply because I remember how notoriously tricky they were to style when they were actually, well, stylish. Our tastes have certainly evolved since the days of wearing velour fabrics and bumster lengths, meaning that teaming them with reliable staples like chunky shearling boots are almost outside of the realm of possibility.

In a sense, it’s almost intuitive to think that bootcut leggings should be styled with these types of boots. It’s in the name after all! But limiting ourselves to these gaudy Y2K-inspired styling motifs almost feels derivative and quite reductive to how versatile bootcut leggings can actually be. So, then, what kinds of shoes work with bootcut leggings best? Thankfully, we have chic dressers and members of the celebrity set to turn to for inspiration.

From tastemakers running to Pilates classes in these slightly flared cuts to more sophisticated spins that see bootcut leggings rendered in more structured fabric, which in turn lend themselves to more elevated shoe choices, there really is a knack to piecing together a sophisticated outfit, and it certainly comes down to your footwear options.

And given the fact that bootcut leggings show no signs of slowing down, it’s only right that you familiarise yourself with these leading styles. So, regardless of whether you plan on reviving the silhouette or are just curious to know what contemporary footwear choices complement this cut best, scroll on for the best shoes to wear with bootcut leggings this season and beyond.

5 Shoes to Wear With Bootcut Leggings in 2025

1. Heeled Boots

Style Notes: It should go without saying that boots and bootcut leggings are a match made in heaven. This is the shoe that lends the leggings style its name after all. For this trend to look its best, however, it’s best to veer away from super sporty variants of leggings and reach for something with a bit more rigidity, like a jersey or wool blend, to really enhance the polish and poise of heeled boots, as Parisienne It girl Sabina Socol demonstrates here.

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2. Lace-Up Flats

Style Notes: With a tapered form through the leg and a gradual broadening around the ankle, striking a refined proportion is paramount when wearing bootcut leggings. As a result, opt for something that’s both low-profile and boasts a slight stiffness to balance out the clean, slim lines. Think: Ghillies, brogues or the very on-trend derbies.

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3. Trainers

Style Notes: Just because it’s the most apparent, it doesn’t mean it should forgo a mention. Trainers are an obvious choice to wear with any type of leggings, purely because of the athletic connotations embedded in both the footwear and the trousers. Its universality also makes it the most versatile choice on this list, as really any trainer works with this shape.

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4. Slippers

Style Notes: To wear leggings is to prioritise comfort, so why not embrace this ethos fully with a pair of slippers? As I’ve waxed on about before, slippers are no longer reserved as a house shoe, with über-luxury brands like The Row making a case for this homely item to embrace the outdoors. If there’s any time to try the trend yourself, it’s with this cut of leggings, as the protruding outline is aptly offset by a softer shoe choice.

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5. Flip-Flops

Style Notes: Whilst this is something you certainly would’ve seen on-screen in The OC, trust SoCal cool girl Kendall Jenner to update this pairing for a new decade. Taking the look for a spin while out in Paris, the supermodel and mogul rejuvenated the trusted outfit formula with a pair of minimalistic leather flip-flops, latte-hued set and mocha-coloured suede bag. As the French say, très chic.

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