9 Back to School Shoes for Tots to Tweens

By Dawn Van Osdell

There’s a collective groan heard across the country as parents peel their kids away from the pool and prepare to send them back to school. A new pair of shoes should make the return to class a little easier on everyone. We’ve rounded up nine super cool pairs that are sure to put some pep in the step of even the most discriminating kids—from toddlers to tweens, and even an irresistible splurge for the tiniest of toes. 

Personalized Toms exclusively for Chasing Fireflies are just right for a get-up-and- go approach to the new school year, especially when it still feels like summer outside. Monogram the light, canvas slip-ons with your child’s name and a favorite icon—like a bow, heart or flower ($48, chasing-fireflies.com).


Thank you, Stride Rite, for your Made2Play line! It features perfectly rugged, playful kicks for both girls and boys, and their “Grip & Go” straps (think: modern-day Velcro) make them just right for busy mornings. Did we mention they are also machine-washable? ($46, stride rite.com)

When the chill of fall arrives—and only the best will do for your new bundle of joy—keep his or her toes toasty in some super-soft booties. These traditional suede moccasins in muted newborn-y colors are from quintessentially French label Tartine et Chocolat, and definitely cute enough to be worth the splurge ($63, available at Bizi Children's Boutique and Little Pillow, both located in Brooklyn, NY).

You likely won’t mind if your preschooler prances out in these spunky Catimini wellies— even on the sunniest of days. Who could blame her for not wanting to save them for rainy weather? Their bold, ethnic print is fun and fresh, and the waterproof rubber just what she needs to stay dry on the walk to school…or to and from the car ($55.00, shopcatimini.com).

Sprout scours the Earth to find cute kid’s gear that is free from harmful toxins and chock full of style and comfort. Their Veyja sneakers are a fantastic find with global appeal, made with organic cotton grown by small-scale farmers in Brazil and rubber from trees in the Amazon. The design is inspired by grown-up hipsters’ favorite trainer, and is sure to be just as big a hit with both boys and girls ($60, sproutsanfrancisco.com.

Classic flats go with nearly everything in her closet—from leggings to dressy dresses. Cool colors, like Winterberry and Deep Sea Blue, from trusty Stride Rite, make them fresh and modern ($40, available September 15 from stride rite.com).

Forget about using a Sharpie to make their sneaks unique. These Chuck Taylors created exclusively for Chasing Fireflies are available as low-tops or high-tops, come in six colors, and can be customized with a name and one of 19 symbols, including a cool lightning bolt or a glittery heart ($42, chasing-fireflies.com).


Florsheim Kids brings big style—now more than ever, thanks to new collections created in collaboration with Appaman, the hip brand known for blending Brooklyn vibes with European style. Your tween will gladly forego his favorite flip-flops for a new pair of Varsity High Top Jr.s ($55, florsheim.com).

For a little (or big) tough guy who doesn’t like a lot of fuss, check out Umi’s Mica chukka ankle boots. Neutral. Comfortable. No fuss. They fit his bill, and yours, too ($65-$70, umishoes.com