We may have previously only associated leggings with a workout or a sofa day, but now, they’re a fully functioning piece in our everyday wardrobe (no matter the plans.) While we’re big fans of leggings with knee-high boots, it seems as though A-listers have cottoned on to a slightly more surprising pairing and are wearing their leggings with one shoe style in particular: Ankle boots.
Yes, you read correctly—ankle boots (and not just UGGS) have made their way back into celebrities’ legging outfits, many of which are heeled iterations. We’ve seen Rosie Huntington-Whiteley, for example, in her long vest, athletic leggings, and pointed suede ankle boots. And then there’s Rachel Stevens who has worn The Row’s beloved zip boots with leggings and a cosy knit.
Need further proof? Scroll for the celeb-approved legging-and-ankle-boot outfits that may encourage you to follow suit.
Style Notes: Rosie Huntington-Whiteley pairs here Wardrobe NYC leggings with YSL ankle boots and looks so chic doing so. Add oversized layers to help balance our proportions and give the look that cool girl touch.
For everyday comfort.
Style Notes: Jasmine goes down the classic route by opting for Uggs as her ankle boot of choice and I just love it. While there’s something to be said for a heeled boot and legging combo, you can’t go wrong with the classics. Add cosy socks like Jasmine for extra comfort during weekend errand running.
SKIMS is very inclusive with its sizing.
After the huge UGG comeback of 2022, we expect to see them again in the cooler months.
Style Notes: Ok, the whole Who What Wear team have agreed: this is an outfit worth copying, stat. An all-black looking consisting of leggings paired with a sleek black roll-neck and stiletto, sock-style boots is just so stylish.
For workouts, or out and about, you’ll wear these on repeat.
We’re so pleased Topshop is still here for excellent footwear.
Style Notes: I just love Rita’s pairing here. Split hem leggings look so good with a classic heeled ankle boot and this is a duo you can easily dress up or down. Wear with a jumper at the weekend or a silk cami and blazer for a night out.
The split is perfect for showing off a great shoe, too.
This sleek pair will pair seamlessly with leggings.
Style Notes: Kate Moss will forever be one of our style icons. Here she’s paired her leggings with heeled ankle boots before adding a printed top and belted jacket. We love it!
These come in sizes XS-4XL.
The mix of patent and suede leather is really nice.
Style Notes: How good does Hailey look in her legging-boot-bomber trio? I especially love how the boots and leggings seamlessly blend into one another.
These are great if you don’t want a high waisted style.
Simple, yet effective.
Style Notes: Who said your ankle boots had to be black? Make like Emily and wear your leggings with a bright or patterned pair.
The elevated legging.
These will also update even the simplest of jeans.
Style Notes: Now this is a cosy winter look with serious style power. Go for a boot that comes up every so slightly higher on the ankle to give your look extra polish.
These would look so good with a chunky knit and trainers for an autumn stroll.
These have just restocked, so get them while you can.
Style Notes: Leave it to Naomi Campbell to pair her wardrobe heroes together to create an effortlessly sleek look. Combat boots give this outfit an extra trend-led touch.
If The Row’s leggings are as good as everything else the brand makes, we’re already impressed.
To wear on repeat this autumn/winter, and every one after that.
This story was originally published on Who What Wear US and has since been updated.