Posted on: December 17, 2023 Posted by: Comments: 0

Leggings have always been one of fashion’s most controversial dividers. Comfort has never been the point of contention here—we can all agree that they’re just about the most enjoyable garment to wear. However, as for their style credentials? They’re often brought into question.

I blame this on the ’80s, where leggings were neon, cropped and usually accompanied by clashing leg warmers. However, over recent years, leggings have made what some would call a comeback—now forming the basis of many a chic minimalist outfit and looking a little different than their ’80s heyday.

Now, classic black or neutral leggings are pretty much the only way forward if you intend to wear them out of the gym. And in weighted fabrics, they look and feel significantly more premium than their retro counterparts. However, one thing even us fashion editors still struggle with is deciding which footwear goes with them.

Your choice of footwear will determine how your legging look is perceived. If you intend on going casual, a pair of trainers will do the trick, but you’ll probably want to steer clear of plimsolls as they’ll look too P.E.-like. After dark, courts might seem like a strong option, but really, they’ll make them look dated.

Instead, I’ve whittled down the six pairs of shoes to wear with leggings that will actually look chic. Keep scrolling and you’ll never have to second guess stepping out in leggings again. 

Style Notes: Leggings started out life as ballerina attire, and now the look has come full circle. Now, fashion types are donning their leggings with ballet flats (on milder days) for a very pretty, very French vibe. This duo works particularly well when a chic stirrup or split-hem legging is involved. 

A favourite amongst fashion people. 

The square toe adds to the expensive feel of this pair. 

This pair comes in so many classic hues. 

M&S’s shoe collection is so strong right now. 

The concealed zips allow you to adjust the shape. 

Style Notes: Chunky boots are a year-round staple, and the good news is they’re probably the easiest shoe to wear with leggings. Whether you opt for an ankle or knee-high, slip-on or lace-up, slip on a pair as you’re running out the door to ensure your leggings ensemble always looks polished. 

A timeless pair you’re wear over and over again. 

These continue to be a much-loved style. 

Pair your favourite cowboy boots with simple leggings. 

A more subtle take on the cowboy trend. 

The zip-hem is a great way to show off the shoe. 

Style Notes: Yes, you can wear leggings on a night out. As we’ve already discussed, courts can make leggings look pretty dated, which is why we instead suggest styling them with some modern pointed-toe slingbacks for an elevated vibe. 

How beautiful are these?

These immediately went on my wish list. 

A chic way to take on the mesh shoe trend. 


These are seriously soft. 

Style Notes: Much like boots, trainers are also a no-brainer when it comes to leggings outfits. And although basically all trainers ‘go’ with leggings, the coolest way to wear the pairing right now is with a sporty ankle sock and a chunky ‘Dad’ trainer. Preferably from New Balance, but any technical-looking number will do the trick. Throw an oversized sweatshirt and a maxi coat (or blazer in spring) in the mix and you’ve got my favourite off-duty ensemble.

An iconic pair. 

A minimalist, retro style. 

These will go with everything. 

H&M offers a cool, affordable version. 

The hero of our outfit builds. 

Style Notes: With the power to make any outfit look instantly glossy, it’s little wonder that we constantly see so many influencers styling their leggings with knee-high-boots. From chunky flat styles to high-heeled, they look elegant either way. 

This chestnut hue is just as versatile as classic black. 

I can’t stop thinking about this pair. 

You’ll wear these with everything until spring. 

This pair also comes in timeless black and an elegant camel. 

So many of our editors rate these leggings. 

Style Notes: Leggings come into their own in the cooler months as a cosy yet comfortable option for every day. But once spring rolls around, fashion people are proving that leggings are just as relevant in warm weather too with the simple addition of sandals.  

You’ll find this modern flip flop on every editor’s wish list. 

This pair is selling fast. 

Yes, you can style your favourite Birkenstocks with leggings. 

These look so expensive. 

H&M always has affordable basics. 

This story was published at an earlier time and has since been updated.

Up Next, 8 Chic Yet Easy Outfits That Are Perfect for Wearing to the Pub This Winter

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