How To Wear Sneakers With Everything In Your Closet

When it comes to fail-proof footwear, sneakers easily take the top spot. They check every box—they're always in style, comfortable with no painful breaking-in period and utterly practical (find us another shoe you can easily get 20,000 steps in.) 

Ready to make them part of your regular rotation? Read on for our comprehensive guide on how to wear sneakers with everything, from bold suiting and matching sets to shorts and long skirts.  

How to style sneakers with everything in your closet

The best sneakers to wear with jeans

Love your denim? Though any sneaker looks great with a pair of jeans, Converse are the perfect shoe for an easy, casual look that feels intentional.

High-tops may seem like an intimidating shape to pull off when it comes to sneakers for women, but with the right balance (an ankle-length pair of jeans and a white tee, for example), it’s a weekend look you’ll reach for time and time again.

Converse Chuck Taylor All-Star Move High-Top Sneakers, $85

The best sneakers to wear with a dress

We love a classic dress-and-sandals combo, but there’s something to be said for the cool contrast between a feminine frock and a sporty sneaker. You can play it safe with a white pair of shoes, or lean into bold styling with vibrant colours.

Adidas Gazelle sneakers are the darlings of spring and summer, and we love this platform style with its fresh yellow and pink pairing. To take the look to the next level, throw on a pair of athletic crew socks. It will give an extra layer of comfort to this excursion-primed pairing. 

Adidas Gazelle Bold Sneakers, $160

The best sneakers to wear with a midi skirt 

A long skirt is practically begging to be paired up with trendy ballet flats, but we actually prefer a timeless white tennis shoe. It’s better for your feet and much more versatile.

Style your white sneakers with an oversized tee, micro-pleated skirt and a silk scarf to elevate them from casual to polished.

Everlane The Day Sneaker, $183

The best sneakers to wear with shorts 

Nearly every pair of shorts in your closet can be paired with sneakers, from denim cut-offs to tailored styles. To embrace the sporty aesthetic, pair mesh sneakers with a roomy short silhouette made from high-performance fabric. You're ready for anything, from school drop-off to a hike.

New Balance 530 Sneakers, $130

The best sneakers to wear with a matching set

When you’re styling a matching set, sneaker options are endless. A classic silhouette work here, but it’s the perfect opportunity to inject some colour into your look.

Our advice: Follow stylist Allison Borstein’s “wrong shoe theory”; that is, do something a little unexpected on the bottom, like a pastel-hued sneaker with vibrant monochrome look.

Puma Palermo Sneakers, $120

The best sneakers to wear with a suit 

Sneakers and smart suiting? We get your hesitancy. Here, it’s all about proportion—stick to a suit with a wider leg, which can accommodate a chunkier shoe, and don’t be afraid to embrace colour to really amp up the unexpectedly playful vibe.

If you want to take inspiration from content creator Grece Ghanem’s monochrome red look, opt for a classic pair of Vans in an eye-catching colour.

Vans Old Skool Shoes, $90

The best sneakers to wear with a neutral outfit

This low-key, city-friendly look is chic in its simplicity. Loose, laid-back layers—particularly the rolled-up trouser and minimalist trench—allow for a sportier sneaker. Try something with a similarly monochrome feel for a sophisticated look that’s also incredibly comfy.

Lululemon Strongfeel Training Shoes, $148

The best sneakers to wear with bold patterns

A chunky, so-called “dad” sneaker plays into the spirited nature of a head-to-toe print moment, while still keeping everything grounded. Not sold on the chunkier shape of the shoe? A longer pant will give you a bit more coverage while you get used to the look.

For a dad sneaker that you can wear with everything, opt for neutral colours, like beige, white, black or grey.

Sorel Kinetic Breakthru Tech Lace Shoes, $110