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Awww that's too cute! I love his little lumberjack shirt. He looks proud and comfortable in his gear
I live in a colder climate and my boy has a few hoodies and coats and boots too! It started with my elder girl, she would get chilly in the winter, now I think the clothes are just made for mini schnauzers lol. They sport them so well and keeps them warm in very cold weather.
I also found (especially when my boy was young) a tighter fitting hoodie would help him feel safer and often when I tried on his clothes, he would just snuggle up and have a nap.
Where we are the snow is often wet and creates huge snowballs or iceballs all over their legs and belly. So in crazy weather like that I made my boy (altered) a few little nylon jumpsuits to fit him and his long legs. I only have the front legs covered because I need the length for legs on the cheaper gear (I sew the back legs on the front as an extension) or just cut off the back leg sleeves because he's really not a fan of 4 legger suits. But I'll place a winter padded harness on top to take him for a walk like that to keep the snowballs off and I find them very useful. He can play around, roll around and jump in the snow in the back garden without the huge meltdown (which must be very uncomfortable).
These are the little nylon suits we use that I altered