Standard Athletic shoes: Get a human from Runner's World to talk about athletic shoes, fit, and standard materials. Look into getting your foot machine checked for balance, arch height, pressure points if you're serious about running. Also the strange sideline of vintage collectible shoes NIB Air Jordans going for hundreds on ebay.

Boots: Work, Hiking. Look for someone from redwing, wesco, justin all American made (not that it matters much) to go over care, fit etc. Hiking: REI

Sandals: First, is it cool for a guy to wear open toe sandals? Not everyone likes seeing less than well groomed toenails and hairy toes sticking out. Second, places ok and not so OK to wear sandals?

Dress Shoes: Wingtips? Two-Tones? Spit polish blacks? What kinds go with what outfits?

Around the house: Most comfortable run to the mailbox type shoes

Bonus: Hunting and fishing boots/shoes. Thermal ratings, gore-tex, neoprene. Cabelas is a good source for both lines.