I have some that are summer only, some that are winter only, and some that are year round. The boots are winter weekends and the boat shoes are summer weekends.
On the non-boot / boat shoes, I never wear the same pair in a week and rarely wear that same pair in a month. Some days it's 2 pair - one to work and one out after work. Some do not get a lot of wear now - the black Park Avenues have been worn maybe 1-2 times in the past year as I don't wear suits to work any more.
I had a couple of pair that did not fit well (I was trying some different lasts). We recently hired a guy out of college and I found out he wears the same size as I do. He was wearing less expensive shoes the typical recent college graduate wears. These 2 pair fit him perfectly, so he got a jump start on his AE collection with 2 relatively new pairs of shoes.