These Are the Only Shoes I'd Even Consider Wearing With Leggings This Season

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.

Shoes to Wear with Leggings: @modedamour

Photo:

@modedamour

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. 

1. BALLET FLATS

Shoes to Wear with Leggings: @anoukyve

Photo:

@anoukyve

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. 

SHOP THE LOOK:

A favourite amongst fashion people. 

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

This pair comes in so many classic hues. 

The concealed zips allow you to adjust the shape. 

2. CHUNKY BOOTS

Shoes to Wear with Leggings: @hannahlewisstylist

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. 

SHOP THE LOOK:

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. 

3. SLINGBACK HEELS

Shoes to Wear with Leggings: @nlmarilyn

Photo:

@nlmarilyn
Shoes to Wear with Leggings: @nlmarilyn

Photo:

@nlmarilyn

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. 

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.

H&M offers a cool, affordable version. 

5. KNEE-HIGH BOOTS

Shoes to Wear with Leggings: @nlmarilyn

Photo:

@nlmarilyn
Shoes to Wear with Leggings: @modedamour

Photo:

@modedamour

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. 

SHOP THE LOOK:

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. 

6. SANDALS

Shoes to Wear with Leggings: @femmeblk

Photo:

@femmeblk
Shoes to Wear with Leggings: @smythsisters

Photo:

@smythsisters

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.  

SHOP THE LOOK:

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

Yes, you can style your favourite Birkenstocks with leggings. 

H&M always has affordable basics. 

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

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