If you want your dog to wear boots/shoes, you gotta start when they're a puppy. Both Teddy and Grey started wearing socks as soon as I got them. Then came the boots/shoes. They're both super comfortable walking in shoes - This is beneficial during winter or if you live in the city where the streets tend to be dirty. 

ALSO, as an avid shoe collector, it's fun to purchase shoes for your dogs.  I usually put lined winter boots during the cold season, sporty (waterproof) boots when we go camping and sneakers during the summer months. Combined, Teddy and Grey will so surpase the number of shoes I own!