For The Boys: The Short-s End of the Stick

My dilemma for the summer: tailored shorts, or denim cutoffs?
As an admittedly preppy guy (my friends have christened me the Preppy Hipster), I have a tendency to lean towards clothing with impeccable construction, but because of the god-awful summer humidity, I cannot bring myself to wearing my tailored trousers. Thankfully, tailored shorts exist, solving my two-fold problem. I love the way a pair of tailored shorts stop right at the knee, and worn with an equally preppy top OR a hipster staple (plaid anyone?), the look is a solution to a common summer style quandary. Avoid looking like a douche and keep the shirt untucked, that is, unless you are in prep school.
Because I am not the standard hipster size (I actually have a profile and don’t disappear when I turn to the side), I have chosen not to try the cutoff-denim-shorts look. Aesthetically, it is a playful, retro way of dressing for summer and far easier/cheaper to get a hold of. Go to thrift store, buy crap jeans, cut new inseam (measure twice, cut once, people!) and wear super shorts! Though, it’s not for everyone. Finish the look with a clever t-shirt (Threadless is a good bet) and canvas shoe with no socks (a high-top is pretty nifty), and you’ll PBR’ing your way to popularity.
For the economically challenged (not unlike myself), H+M has a few offerings in both styles. Try a tailored and denim pair to figure which works best for you. Be warned, though: you can’t be just anybody with either of these choices. As with any fashion decision, you have to own the look, and in the immortal words of Tim Gunn, “make it work.”