In case you haven’t noticed, children’s footwear has come a long way in recent years. Forget cartoon characters and light-up runners (although they will always have juvenile fans). The coolest new styles are fashionable and surprisingly sleek. From retro-inspired sneakers to swish leather flats, the best kids’ shoes these days look like they could be miniatures from your own wardrobe! 

Kids’ feet do grow pretty quickly, but the reality is that comfortable, well-made shoes are always a worthwhile investment. Whether they’re barely in daycare or already a seasoned grade schooler, here are the styles you’ll want the kids to try on for size next time they’re at Square One!

We’re loving the classic styling of The Children’s Place’s cool desert boots. Perfect for fall hikes or just walks to daycare.

The Children's Place

Boat shoes are an iconic summer staple, but would look just as cute for back-to-school with a pair of rolled khakis! These Gymboree ones come in four equally cute hues.


Available in both toddler and preschool sizes, consider Nike Air Force 1 Mid sneakers from Kids Foot Locker super comfy collectibles (with shock absorption and a solid rubber outsole). 

Kids Foot Locker

These well-priced metallic Converse Chuck Taylor hi-tops, available at Sport Chek, might just be the perfect school-to-party sneaks!

Sport Chek

Leopard-print is the fashion lover’s neutral; these slip-ons from Gap Kids are fun enough to be paired with a dress, but casual enough for jeans, too.

Gap Kids

Chelsea boots look great with both leggings and jeans, and can easily be dressed up or down. This black pair from H&M is sure to be a fall wardrobe staple!

If your kid loves denim, you’ll want to grab these charming Old Navy sneakers in an unexpected chambray fabric.

Channel Charlotte Olympia’s cat shoes with these adorable espadrilles from Gap Kids. They can wear them with bare legs now, and paired with tights in a few months.


Justice’s perforated boots are perfect for transitional weather-dressing and the perfect way to get a head start on fall’s Americana runway trend!


Truc Nguyen

Truc Nguyen is a Toronto-based freelance stylist, fashion editor, and writer. She’s worked as a style editor at Flare, Teen Vogue, Vogue Living, and StyleCaster​.com​​, and is a co-founder of Editors Inc​.