I wear sandals whenever possible & practical
I wear my "Gym Shoes" (new balance) whenever possible & practical (provided I am not wearing my preferred sandals)
I wear my "dress shoes" when I am at work or at slightly more formal setting (Nunn bush, propet, etc)
I wear my Boots when necessary (12+ inches snow)
As far as pants go
I wear shorts when practical (not at home, under 6 inches of snow, above 10 deg F), and when possible (not at work)
I wear jeans when practical (not at home, over 6 inches of snow, or colder than 10 degrees F) and possible (not at work).
I wear "dress pants" when I am at work. (slacks that are not cargo pants or jeans)