For the last several summers I've done the same dance - go to store, buy shorts I don't really like, wear them one summer, repeat. It's a comfortable dance except for two things: I never get shorts I like, and it's expensive.
Normally the advice parceled out by GQ verges on the mundane, but a recent article grabbed my attention, sat on it, and refused to let it up until I did what it asked. Why buy ill-fitting, expensive shorts, when you can make your own?
The most compelling reason is fit. Most shorts for men are cut as though you're going to hide small mammals in the leg holes. More tailored shorts charge for the benefit of actually fitting. Pants, on the other hand, fit the way your lower garments should - close to the leg, with a proper amount of space for your...er...important part.
From left to right: Club Monaco, Zara, Enjoi.
I bought the Club Monaco pants with the specific idea that I would hem them into shorts. Pants (or for the Brits, trousers) of a lighter fabric probably won't take well to a simple cut. Get a tailor to hem them about an inch above the knee - this might be shorter than you're comfortable with, but hemmed shorts need to be a little neater.
The middle pair I wore as pants for a few years before taking a rolling blade to them. I cut these right at the knee (anything longer, unless you're going surfing, just cuts your leg at an awkward place.)
A little faux-seersucker for the summer. I opted for a narrower hem with this fabric. Ask your tailor.
One final note - those oddly coloured remainders hanging on the sale rack might not work as pants, but will work surprisingly well as shorts. Club Monaco regularly has weird ones for $9.