I recently received a message from a grandmother looking for shoes for her grandson and thought I’d share my favorite toddler boy shoes here as well! If only because I’m sure I’ll be ordering alternate sizes of everything for Peter in a few months since our boys were born at opposite times of year. 😂


toddler boy shoes - suede chelsea boots

Starting with shoes for the current season, these suede chelsea boots are easily Teddy’s most worn pair of shoes for two winters running. I recommend ordering one size up since there’s no zipper. So you’ll need to pull them on and off! It looks like the brown may be sold out right now but they also come in navy blue.


Teddy often gravitates towards the bright color of these Hunter rain boots that have seen a lot of year-round wear in our house. And run on the roomier side so they’ll last more than a few months. I’ve also heard good things about this more affordable pair that comes in a bunch of cute colors.

Sperry snow boots - SHOES FOR TODDLER BOYS

I got these Sperry snow boots for Teddy this year and I love that they look like a mini version of my L.L. Bean boots which don’t come in toddler sizes. Definitely order one size up in these!

toddler boy shoes

Teddy has dubbed this pair his “cozy boots” and for good reason — I have the women’s version and they are my go-to pair for lounging around the house. The toddler pair runs true to size. And has a zipper so they’re easy to get on and off!

toddler boy shoes - Elephantito

These Elephantito driving loafers kill me!

I first ordered a pair when Teddy was a baby and I will say that the toddler size has gotten a bit more scuffed up since he’s constantly on the move. So they’re probably a better choice for dressier occasions rather than trips to the park. 😉 Smaller sizes are listed here and larger sizes here. Order a size up in these as well!

toddler boy shoes - L.L. Bean slippers

These L.L. Bean slippers are the best! I just ordered new pairs for both boys for Christmas and was pleasantly surprised that the smallest size fits on Peter’s fit at almost 9 months.

toddler boy shoes - Superga sneakers

When it’s warmer out, I love putting Teddy in these Superga sneakers.

The velcro makes them easy to get on and off (especially if you order one size up… clearly a recurring theme in my process!) But they still look more classic to me than most other velcro sneakers for kids. We have them in white and navy and just throw them in the wash when they need a refresh!

toddler boy shoes - Native shoes

These Native shoes are my favorite for easy on and off all summer, especially at the beach. True to size!

toddler boy shoes - Sperry toddler boat shoes

I’m a sucker for dressing the boys in anything that’s a mini version of something my husband wears. So these Sperry toddler boat shoes were basically irresistible. This velcro baby pair is equally precious if you’re due this spring or summer!

Any other favorite toddler shoes you swear by? Do tell!

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  1. Have to add See Kai Run to the list! They are so durable and perfect for new walkers. Some of the designs are obnoxious but they have some really sweet plain colors that have been in heavy rotation for us every season.

  2. My older son is on his fourth pair of Adidas Grand Courts – they’re Velcro, so easy to get on and off, but the black and white is classic and goes with pretty much anything. We also love our Hunter boots! The style we have has little handles and he can get them
    on and off on his own, which is awesome!

  3. We are more of a sneaker family! The Converse Chuck Taylor velcros and the toddler Puma velcros are our favorites! Super cute and last well. 🙂