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.
Shop the Shoes:
Sock boots are one of the biggest footwear trends this season.
Block heels can sometimes feel dated, but when paired with another slightly polarising trend, they balance out and result in something considerably premium.
A razor-sharp heel and a square toe is such a sophisticated pairing.
If money were no object, Khaite's Nevada boots, now with a contrasting patent toe, would be one of my first dream purchases.
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 Derby shoes.
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Thanks to Celine's incumbent creative director Michael Rider, Derby shoes are back on the sartorial agenda.
Another French option for you to covet.
This ankle-high Mango style is putting the "boot" in bootcut leggings.
Lace-up flats have been reigning since the summer.
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 bottoms. They're universality also makes them the most versatile choice on this list, as really any trainer works with this shape.
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Asics have swiftly overtaken as the stylish sneaker du jour.
A chicer alternative to Sambas.
Arguably the hottest designer trainer of the year.
The textured finish is really what makes these extra special.
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 bootcut leggings, as the protruding outline is aptly offset by a softer shoe choice.
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The definition of walking on clouds.
Perfect for the beaches of Majorca and the streets of Chelsea alike.
Still as luxurious, just slightly more subtle.
Textured heaven.
5. Flip-Flops
Style Notes: Whilst this is something you certainly would’ve seen on-screen in The O.C., trust SoCal cool girl Kendall Jenner to update this pairing for a new decade. Taking the look for a spin whilst out in Paris, the supermodel and mogul rejuvenated the trusted outfit formula with a pair of minimal leather flip-flops, latte-hued matching set and mocha-coloured suede bag. As the French say, très chic.
Shop the Shoes:
Such a great pair for those who want to transition out of rubber styles.
Arket does elevated essentials so well.
I've seen Kendall Jenner wear this exact look, right down to the cream satin trousers and black leather flip-flops.
The cushioned insole and cable-like straps are design elements that give this pair an extra level of consideration and thought.
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