Boots with shorts!? NEVER!
That kind of depends on what kind of boots we are talking about. There are those ankle high lace up boots that look that we call "hiking boots" around here It is common to see guys wearing those with shorts -- just not with dress socks of any color. Cowboy boots with shorts? Not so good unless you are a girl. Then it looks pretty sexy.
I only give passing glances before rolling my eyes.