P.S. I am totally not a dog expert. These are just my first-hand observations.
1) Find appropriate footwear (for the humans). Wish's wardrobe needs (or lack therof) are coming up later, but this is by far my top tip. For us, this meant finding some winter boots for the first time in many years. Even when there wasn't snow, it was so much more comfortable to have tall boots for extra warmth - and when there was snow, boots were essentially mandatory. I picked out this pair of Lands End boots in glacier blue, and they were one of my winter must-haves, even though I learned when the snow turned to slush and puddles that they are more water resistant than water proof. (But either way, still super warm.) Josh got some very serious winter boots for his birthday and I think he would endorse finding a good pair of boots just as firmly.
2) Figure out what your pup needs to be comfortable and safe. I heard a lot about booties for dogs going into the winter, and I harbored little daydreams about Wish wearing adorable little booties as he trotted merrily through the snow. It turned out that wearing booties was not on his wish list (puns on our dog's name are always welcome at Miles and Laurel). I think it would be a two-person job to put the booties on him, since it sure didn't work the one time I tried by myself. Anyway, the booties exist because some dogs are bothered by salt and sand in their paws, but that didn't trouble Wish, so the booties were out. If we were walking through heavy, wet snow, he sometimes got clumps of snow stuck around his paws and would need a break (or help) to remove them.
Also, he basically comes with a big sweater - do you need me to post another picture of him? - so he didn't need a jacket, but some dogs with thinner coats do.
Okay, another picture:
5) Remember to play. If your dog likes to play in the snow, I definitely encourage this, because besides being gloriously fun for him, it really boosted my spirits during a sometimes dreary season to watch him roll, sniff, gallop, and trundle in the snow. There's no doubt we laughed more than usual this winter because of this goofball. I only wish we could let him off-leash to see him really go wild. He reminded us that winter can be very fun.
More seasoned dog owners, what did I miss? Does yours like to play outside or prefer to wait til spring? Does he or she need a jacket or booties? And what's your best tip for taking care of your pup during a cold winter?