I most often don’t condone men over the age of 23 to wear shorts at any time unless an event specifically calls for it (swimming, etc). Most of you will go against this recommendation and wear shorts anyway. So, at least, may I say, if you are going to wear shorts, don’t wear stupidly huge cargo shorts. How much stuff do you really have to carry around that you can’t fit in a few pockets anyway?! Don’t let the pockets get crinkly and don’t leave them unbuttoned. Don’t let them hang below the knee. Don’t let the edges fray or, worse, buy them with frayed edges. Mostly just don’t.

Some examples of awful cargo shorts at the always amazing tourist trap Navy Pier today:

Blue Man Group

Mess.

Furthermore, if you must wear shorts, do not wear them with white socks and running sneakers–unless you are actually running. The reason you may wear shorts is because it’s hot. So, wear something that indicates the same for your feat. Consider a flip-flop (see my post on manicures/pedicures before though), a nice boat loafer, or classy slip-ons depending on your taste and look…without breaking the bank.

Piperlime Flip Flops $12.50

Globe The Don Slipper: $35-50

Slip Ons from Urban Outfitters: $24