How To Choose The Best Winter Boots For New Walkers

Winter comes around every year whether you love it or not. And as predictable as the turning of the seasons, your little one’s boots from last year aren’t going to fit this year. Buying winter boots doesn’t have to be a big ordeal. We’ve got some tips and tricks to help you choose the best winter boots for new walkers now!

What To Consider When Choosing The Best Winter Boots For Your Toddler


Winter isn’t the same everywhere. Are you looking at a California winter or an Alberta winter? Choosing the right amount of warmth for your little one’s feet is important to make sure they’re not running too hot or too cold. 

Some brands may have temperature ratings available so that can help, especially if you’re looking for really cold-weather wear. Other things to look for are if the boots are insulated, what type of material they’re made out of, if they have a liner, and how they are secured. 

Think about what type of warmth you need for your boots in the winter and use that as a base gauge as to how lightweight or extreme your toddler’s boots need to be. 

And remember, how a boot fits and what’s worn with it can affect the warmth. If boots are too tight or if heavy socks are worn without enough room, it can actually make your child’s feet colder as there’s no room for air to circulate. Roomier boots are better, especially if you want to wear wool socks. 


Being a new walker is hard enough without having the ground slip out from under you. If your toddler is heading out on icy surfaces, a boot with a heavier tread can help them keep their footing. There is a trade-off here, though, as if boots are too heavy it can cause your toddler to fall over themselves even without the ice. 

Think about the environments your little one will be out in and the type of activities they’ll be doing. If it’s going to be a lot of time in the stroller or being held, something more lightweight with less tread will do just fine. If this is a full afternoon of sledding or snowman building, something a little more heavy-duty is probably a good call. 


Nothing is fun if your boots are rubbing on your feet and giving you blisters. Making sure your child’s boots are comfortable on their feet is key to them enjoying themselves this winter. 

Comfortable boots are made out of materials that don’t rub or irritate their feet. Boots with soft linings help keep feet warm and comfortable. 

Getting boots on and off with ease also increases comfort as their little feet don’t have to be continuously shoved into and pulled out of tight boot tops. Look for boots that have wide openings so they can step in and out of them easily without scraping the sides of their feet. 

And laces are usually a drag. They hinder independence for little ones, can’t be adjusted or fixed without taking off gloves and freezing your fingers, and can be a pain to remove in a hurry if there’s a potty emergency. Boots with velcro, drawstrings, or hook-and-loop fasteners are a toddler’s best friend. 


Getting the right fit for toddler boots is very important! Ill-fitting boots lead to cold feet, snow-filled boots, heel slips, and falls. 

Boot Sizes are Deceiving

Winter boots can be deceiving, especially those with thick soles and rubber lowers. The amount of room inside the boot can be a lot less than you think from the outside. For heavy boots, don’t try to hold your child’s foot against the outside of the boot to check for fit. That will most likely lead to squished toes in too-small boots. 

If the boot you’re looking at has a liner, pull that out and use that as a gauge for fit instead of the boot itself. It will give you a better picture of the real amount of room inside the boot. 

Along with that, trying to gauge fit by pressing on the toe of the boot with your child’s foot inside won’t give you accurate information either. Heavy boots are too thick for you to properly gauge where in the boot their toes reach. 

Getting an Accurate Measurement

The best way to ensure a proper fit is to measure your child’s feet and compare that measurement with the boot’s sizing guide. To do that, have your toddler stand on a piece of paper and draw around their foot. Now measure from the heel to the longest section of the toe. You now have their foot measurement! 

For more detail on how to take proper foot measurements, we have a whole page including a video on getting measurements for Jack and Lily boots and shoes. Have a look here for more support.  

Should You Size Up In Toddler Boots?

Once you have a proper measurement of your child’s feet, we need to connect that measurement to a boot size. Some things to remember: 

  • Little feet grow fast. You don’t want to order boots that are exactly the right size now because, in 3 weeks, they won’t be anymore. 
  • What will your child wear with their boots? Normal socks? Thick wool socks? If you’re planning on pairing thick socks inside their boots, you need to make sure you’ve sized appropriately to make room for that. 
  • Tight boots = cold feet. If you want a pair of boots that will last them all winter, then you need the boots you buy in October to still be roomy in March. 

That all being said, if you plan on having just one pair of boots for a season and want to layer thicker socks inside them, we recommend going up 2 sizes from your child’s initial measurement. 

If you live somewhere with a short winter and don’t plan on layering thick socks, or if you’re open to buying boots again mid-season, you could probably get away with going up 1 size. 

Shop Snow Boots For New Walkers Now

At Jack and Lily, little feet are a big deal. And as a Canadian company, we know better than most the trials of keeping little ones active, warm, and safe in the winter months. We have footwear for every style and need, with warm, cozy moccasins perfect for a winter wonderland stroller ride, to durable walking boots that will stand up to their first steps. 

Have a look at our boot collection for toddler girls and toddler boys now and find the perfect pair for your little one!