These Are the Only Shoes I'd Ever Consider Wearing With Leggings

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.


(Image credit: @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. 

The Best Shoes to Wear With Leggings:



(Image credit: @honeybelleworld)


(Image credit: @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 Ballet Flats:


Lois sterling influencer

(Image credit: _loissterling)


(Image credit: @msrachelstevens)

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 Chunky Boots:



(Image credit: @nlmarilyn)


(Image credit: @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. 

Shop Slingback Heels:



(Image credit: @honeybelleworld)


(Image credit: @kingharriett52)

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.

Shop Trainers:



(Image credit: @nlmarilyn)


(Image credit: @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 Knee-High Boots:



(Image credit: @femmeblk)


(Image credit: @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 Sandals:

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

Emily Dawes
Affiliate Editor

Emily Dawes is the very definition of a fashion multi hyphenate. An editor, stylist and writer with over eleven years’ worth of experience in the industry, Emily is known for her impeccable taste, elegant outfit choices and being able to spot the next big thing in fashion from a mile off. Our readers loyally trust her advice and shopping suggestions; so much so she began her own column documenting the most expensive-looking pieces on the high street, which has become a top-performing piece of content for the Who What Wear brand.

Emily has worked for Who What Wear UK since 2020 in a myriad as roles, spanning from contributing editor and branded content editor. Now, she holds the position of affiliate editor and is responsible for the brand’s overall affiliate strategy, ideation and content execution. Working closely with Who What Wear UK’s affiliate manager, Emily has been instrumental in securing and nourishing brand partnerships, surpassing her goals as standard. Leading the team in tentpole shopping moments including Black Friday and Peak Trading, with Emily’s guidance and leadership, team Who What Wear is in a stronger affiliate position than ever before.

Prior to joining the Who What Wear team, Emily served as YOU Magazine’s acting fashion editor where she managed the fashion team and oversaw all fashion content output for the fast-paced weekly title. Emily is a stylist in her own right, having worked with a slew of VIP clients including writer and television personality, Elizabeth Day, as well as styling and art directing several celebrity cover shoots for glossy print publication, Grazia. Her adept fashion knowledge means brands regularly sought out to work with her as a consultant: previously she has developed marketing and content plans for brands for Cocoon and Edge of Ember. Before entering the industry, Emily obtained a Bachelor of Arts in English and American Studies with International Study from Nottingham University. Fun fact: Emily spent a year studying in America which saw her join a sorority during her time there.

When she’s not working or tracking down the chicest, new-in items to share with our audience, you’ll find Emily bestowing her East London home with her stylish flair, reading everything from the classics to cowboy romance novels and escaping to the country with husband, baby boy and dog, Roo, whenever she can.

Emily is currently on maternity leave.