If you haven't already, you should read my 1,000 hours outside post. We know in the midwest with extreme weather, it can be exhausting getting toddlers layered up to go outside.
Here are the items we use.
We typically use a fleece sleeper as a base layer. It keeps him warm, and there's nothing to ride up to expose skin to the elements. If you can get one with a 2 way zipper, this is what I would recommend for easier diaper changes especially if you're going out to a park to sled or to play when it's very cold. Sometimes we put on an extra thin layer under the fleece sleeper, like a long sleeved onesie. We can also fit wool socks on in his footies to keep his toes extra warm.
I got Jay's toddler snow bibs, ski pants, and winter coats all from facebook marketplace for cheap. I would recommend sizing up for layering purpose. We have all fleeced lined coats with hoods. His snow bibs come up to his chest and they are not overly bulky but they do keep him warm.
I will say that boots and mittens are the absolute hardest part for us as far as dressing and functionality. We are currently using these:
*I am not affiliated with Target or Amazon, unfortunately. These links are all items we have bought and used for Jay to play outside in the snow/rain with.*
My favorite hats:
This one is a little big for him at 18m but overall it's still very effective with room to grow. It's especially helpful for really cold days to keep his nose and mouth covered.
Mittens:
They're so difficult to find good ones that allow them to use their hands, and that keep them warm. These sherpa lined ones are water resistant and very warm, you may want to stock up on extras and keep an extra set with you on outings in case they get too wet from snow. We have 3 pairs of these
Boots:
Rain Gear:
I will also say that both pairs of boots, rain and snow, are difficult for my toddler to walk in. The rain boots are a little easier because they're less bulky and lighter.
We cloth diaper so we already have a ton of wet bags on hand, these are smaller travel ones that you could fit base layers in or an everyday outfit from rain. They're also super handy to have in case of a diaper blow out.
If you needed/wanted to put a towel or outer snow/rain layers in a bag to transport home, they do make these bigger ones as well.
Wool socks:
I hope this post and these links are helpful. Layering up to play outside doesn't have to be dreadful!