Who Wears Short Shorts?

An old middle school buddy of mine named Matt offered up a suggestion a while back by saying, "You should do a post on what shorts to wear. Also, tell dudes to stop wearing those giant cargo shorts from the early 2000's." Ask and ye shall receive, sir. First things first, here's a primer for what makes for a good pair of shorts.

As I've discussed before, the most important aspect of looking good is how your clothes fit. You can spend $30 on a well-fitted t-shirt and jeans outfit and look great, and you can just as easily spend $2,000 on an ill-fitting suit and look like hell (well, maybe not just as easily). Shorts, like bathing suits, are not exempt from this rule. They should fit snugly but not tightly around your waist and the inseam should end about 2"-5" above your kneecap (shorter inseam for smaller guys, longer inseam for bigger guys). An important rule that's often ignored is that the circumference of the leg opening should be relatively slim as well. If the circumference of your thigh is eighteen inches, then the short's legs should be, well, not much more than eighteen inches.

Material for shorts should generally be limited to linen or cotton, oftentimes khaki or chambray. Denim shorts are for children. As far as color and pattern is concerned, I suggest that you have a couple of basics like dark blue and tan, but branch out as far as you're comfortable. White, light blue, yellow, or mauve shorts? Hell yes. Crazy Bermuda and patchwork madras shorts? Indeed; so long as they're paired with a solid shirt, you're in business. Sockless feet tend to look better with shorts, and you can buy socks that are more or less invisible from Banana Republic and H&M.

Second things second, I'd like to accommodate Matt's other request and type it for all to see:

Dudes, stop wearing those giant cargo shorts from the early 2000's. If you have that much stuff to carry, get a messenger bag.

Finally, when I was in Greece there was a guy who had drawstrings at the hem of his shorts. He'd pull the legs up high and tighten the drawstrings to the max. I have no idea how the physics of this worked out, but doing so caused the shorts' legs to shamelessly place his junk front and center for all to see. If you have to ask how or why this is poor form, I'm not sure anyone will ever be able to help you.