Definitely get him a good, warm coat. There are lots of places that make them. You can always check out Mike's photos (Alaskayorkie) of Eddie and Jack. They have cute coats and boots on all the time for the Alaska snow and love being outside.
I have a few different coats for Sissy, some lighter, some heavier. She wouldn't wear boots last year but she was still a young pup, so I might try them again. I don't like winter myself, so I didn't try walking her last year. She only went outside to potty and came right back in.
I can also tell you that when we had snow on the ground (which was much of the winter), I kept a portion of the grass shoveled for her to go on, cause she didin't like the snow.
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