I always wear shoes because I'm girly and like to make sure my mayor is wearing a complete outfit. Of course, this is usually while I'm playing the game in my PJs, lol.
Hahaha what a good question to ask and I had fun reading all the answers.
I wear my shoes most of the time for all my characters. I play as my mayor character the most though and she currently wears the tropical island-ish looking flip flop.
The only time I take it off is when I go diving and when I want to run around my town on the paths when it rains in my town : ]
I always wear my shoes. I never even knew you could take them off till a month ago. I don't understand why people don't wear them. Plus my inventories always filled so I'm to lazy to take them off.
I haven't decided on my characters' seasonal outfits, but they always wear shoes. Though this thread has made me think about making one of them go barefooted during the summer...
First day with no snow the shoes come off and all my players run around barefoot until September. Sometimes I put flip flops on them. Sneakers for awhile and than I switch to shearling boots for winter.
During the summertime when I get the tan I wear aloha shirt and shorts and no shoes but I will wear the cool boots that look like sneakers during any other season