7 best shoes to wear with leggings this season

Working out what shoes to wear with leggings is no easy task and we all know the right pair of shoes can make or break an outfit. Traditionally seen as gym wear, leggings can be tricky to accessorize, but once you've nailed this aesthetic, you'll be able to wear leggings for a host of occasions.

Suffering a bit of a bad wrap over the years, learning what shoes to wear with leggings is no easy sartorial task and creating chic leggings outfits that give runway vibes over 'just off for a run' feels takes some practice. The fitted silhouette is favored by many for its contouring ability and now thanks to modern fabrics and different styles, such as stirrup and split hem leggings, leggings are once again in the fashion spotlight. And while they're enjoying being top of the style game once more, there’s no denying how comfortable they are too.

Obviously, your choice of footwear will depend on what look you’re going for and your activity for the day and while trainers and ballet pumps are for more casual outings, a mid-heel mule or a high-heeled ankle boot will look super chic for evening drinks.  

THE BEST SHOES TO WEAR WITH LEGGINGS - INSPIRATION FROM A FASHION EDITOR

Such a wardrobe staple, you might be wondering why deciphering what shoes to wear with leggings is so tricky. After all, there seems to be less struggle with other basics, such as jeans. 

Fashion stylist and presenter Emma Lightbown, believes the gym connection can make it tricky for people to work out what shoes to wear with leggings.

“Because of the sport and activewear origins of leggings, many people struggle to know what shoes to wear with them other than trainers. However, leggings work with almost all shoes – it’s just about creating the right balance for the rest of your outfit.”

1. How to style trainers with leggings

When you think about what shoes to wear with leggings, trainers are pretty much the first choice. However, if you’re looking to wear this ensemble outside of your workout, there are a few things to consider.

Go simple and choose either black or white trainers to team with plain black leggings. The best white trainers for this look are oversized and chunky, giving a nod to the 'Dad trainer' shoe trend 2022. The oversized trainer works because it balances out the tight fit of the legging and gives a much more contemporary.

While full-out athleisure wear such as your best hoodie and quilted jacket work with these shoes, sharp accessories will keep it looking less chilled out and more styled - such as adding your best designer tote bag to give a more polished feel. 

Style tip: This doesn’t have to be a sporty look, according to Emma.

“Consider teaming your trainers and leggings with a chunky knit and a crossbody bag or finishing off a simple t-shirt, leggings and trainer combo with a smart trench coat,” she says.

2. How to style high heels with leggings

If you get it wrong, heels with leggings can look like you’ve just walked off the set of an '80s movie. The key to this look is to keep it simple when it comes to choosing the style of your high heel.

“I love a classic court shoe with leggings,” says Emma.

“You don’t want anything too fussy as it can look cluttered next to the slim fit of leggings, so avoid ankle straps, Mary Janes, and anything overly strappy. Keeping it simple with a chic court shoe will help elongate your legs rather than shorten them.”

Popular among the fashion set, courts look chic when worn with a stirrup or split hem leggings. It makes them look much more considered and less like you’ve put a pair of heels on with your gym gear.

Style tip: Black leggings and black heels are super chic, however, if you're nervous about bright color clothing but really want to add a flash of color to your outfit, teaming black leggings with bright heels works really well.

3. How to style chunky boots with leggings

Probably one of the easiest shoes to wear with leggings are a pair of chunky boots. Whether you choose hiking, biker or DMs, they will add a touch of contemporary cool to any legging outfit. Prefer a flatter Chelsea boot? While they will work, the best Chelsea boots are those that have had a 2022 upgrade in the form of a platform or lug sole. 

The chunkiness of this style of boot balances out the slimness of the leggings and also makes sure they are winterproof in an instant - just add your warmest leggings. This is a look that can work for a night down the pub or a walk in the country - a quilted coat is the best coat trend to finish off this look this season.

Style tip: Looking for easy Christmas party outfit ideas? Try an embellished biker boot with added sparkles and team with pleather leggings for a look that’s comfortable and stylish.

4. How to style ballet flats with leggings

One of the big fall winter shoe trends 2022 has to offer is the ballet pump. That's right, the footwear beloved in the mid-Noughties by Amy Winehouse and Kate Moss is back. And what's more, it's one shoe style that works really well with leggings.

When teamed with leggings, this combo definitely has a French clothing brand, retro vibe to it, which is probably why fashionistas are wearing them once more. The minimalist look of a ballet pump is great for those more streamlined outfits such as an oversized blazer teamed with leggings.  

While ballet pumps look their best with bare feet, style icons like Alexa Chung have shown that pumps and socks can work with leggings - just stick to neutral shades in both the shoes and socks. 

Style tip: To give your look a more modern edge, choose ballet pumps with square or pointed toes or with a strap going across. 

5. How to style knee high boots with leggings

The beauty of leggings is their super slim fit, which means they're ideal for learning how to wear knee-high boots and really show this boot style off. Great for pairing with this season's must-have footwear style, the best cowboy boots for fall are packed with intricate detailing. Just add a blazer and tee and you’re good to go. 

Alternatively, if you want to keep your look more traditional and less trend-led, opt for a monochrome color palette and match your boots to your leggings for super leg-lengthening properties. 

Style tip: Want to be a bit more daring? Emma suggests teaming your leggings with this season's on-trend thigh-high boots.

"Wearing them with leggings is an easy way to try out this trend and can look super stylish paired with a white shirt and tailored blazer," she advises.

6. How to style loafers with leggings

You can never go wrong with flats when you’re working out what shoes to wear with leggings. In particular, leggings are great if you’re wondering how to style loafers - they're a natural partner for these pared-down trousers.

Emma suggests tapping into the preppy vibe - as seen in Paris Fashion Week street style snaps, if you’re going down this route.

“Think preppy. A stylish knit draped over your shoulders paired with an oversized shirt, a longline blazer with a simple t-shirt underneath or teamed with a tailored coat,” she says.

Style tip: Like with trainers, chunky loafers will work much better with leggings than a slim-line loafer. Choose a thicker, ponte legging to make this look more office appropriate.

7. How to style mid heels with leggings

Mid heels have previously never quite looked right with leggings, perhaps thanks to the gap between the bottom of the leggings and the top of the shoes. However, thanks to the new split-hem legging, this heel height now works really well.

The best mid-heel shoes to wear with leggings? Well, it all depends on what you want to dress for. A block heel works well with a blazer for a more office-appropriate look, whereas a kitten heel mule looks directions with leggings and a corset top and blazer on top.

Style tip: When it comes to split hem leggings, longer always looks better - and then wear with a higher heel or a chunky trainer so that they’re not dragging on the floor.