There are a lot of ways you could go, but you should certainly branch out some. Since you are not about to go out and buy a closet full of all the possibilities from dress blacks, wingtips, bucks, deck shoes, sandals, tux shoes, and a variety of loafers, I thought about the most versatile pair of shoes I own. Actually I have them in both brown and black. The brown go with shorts (believe it or not), jeans, and any color of slacks. In a pinch you can even wear them with black. You can go hiking in these things because of the soles. The nubbins on the soles can be a little slick on wet surfaces like tile or stone. I often go out of town with nothing but these. I wear them to work most days. They are more comfortable than tennis shoes to me. They slip on, but stay more secure than any other loafer. They are from Timberland and are less than $100. The brown ones really are not as shiny as this picture.
