Hellobee Boards

Have you tried crocs? They're not the cutest but those are the only ones my son will wear because they're light and flexible.

My son is 2 1/2 and has fat feet and legs and I can't get his feet into most traditional boots. Last year we used Stonz over his regular shoes, but the winter was so mild he only wore them a few times.

For this year I got Merryluks by Merryweather Outdoors (link below). They are similar to Stonz in that they are very flexible and soft-soled, but they do have a stiffer sole and more insulation. I bought thick wool socks for DS to wear with them and they fit well and he didn't have any complaints when we tried them on.

At 19 months, I don't think your son needs to get used to wearing regular boots. That will come naturally as he gets older. For right now I would prioritize whatever fits well, is comfortable for him, and will keep his feet warm and dry.

http://www.merryweatheroutdoors.com/products/

I ended up getting Kamik Icepop for DD. I think they're an older model (that would explain why I got a good deal on them). I expected them to be really heavy, but they're pretty light. They're rated to -25F/-32C, but because the sole itself is thin (if you take out the lining) they're not so heavy.

DD was thrilled to walk around in them. She doesn't like wearing socks and I imagine these are really warm, so I was really surprised! She was walking and running all around the house!

Two things to note: they run small. The lining is a thick felt that's narrow, but since the boot itself is like a little dome, it fits OK. I bought a size up because of the lining. The top mesh part is more pliable than what it looks like in the pictures.

As for Crocs, DD has the rainboot (unlined) and the ankle part is crazy tight! She has a fat foot and it's now impossible to put them on her with thick socks. She runs in them fine, but since they're stiff in the ankle, she's less agile in them. I loved them on her when they were still too big and it was easier to get them on and LOVED how they didn't fall off. But I now I realize they're a summer rain boot and can only be worn with thin socks.

Have you tried Bogs? They looked interesting and comfortable. We liked the look of Kamiks, but ended up getting a good deal on Lazy Ones, so that's what we got this year.

We have air walks for our snowboots, but I bet he wouldn't be too hip to them as they are rather stiff.

I bought a brand called Richter for DS last winter. They open wide and are Gore-Tex, so they are waterproof. Since you are in Canada, I assume you will be dealing with cold and snow for the winter? I would not get regular rain boots, they won't be warm enough. Get waterproof winter boots.

If you are looking for rain boots (in addition to winter boots), we have had good luck with the Aigle brand.

@Sammyfab: looks like the ones I saw were out, but I did find this deal:
http://hipfeet.com/proddetail.asp?n=Bogs+Baby+Boot+Blue+Monkey+Kids%27s&prod=5507