When it comes to shoes, you don't really need more than a few pairs of wing tips or oxfords. They're classics. And I wear only black shoes in the city. Brown ones are for the country.
Seersucker and khaki suits are the key to looking put-together in the summer. I also wear shorts year-round. And I would never say never, but I don't wear sandals. With shorts, it's wing tips and tennis socks.