The picture above is definitely cool for all the obvious, unsaid reasons– and also for fact that it shows a time in menswear before the short sleeve shirt was banished to Land of the Nerds. The difference between looking cool, or looking like a tool in a short sleeve shirt is a very fine line indeed. You might think that the one fool-proof way to an acceptable short sleeve sportshirt is to start with long sleeves and roll ’em up– and you aren’t too far from the truth. I happen to like a short sleeve shirt from time to time, but always under strict observance of my two hard & fast rules–
No neckwear, Never with shorts. First of all, there’s no such thing as a short sleeve dress shirt– never has, never will. It’s just a bad dream that bad people keep forcing on us. And secondly, I’ve never been a big short-wearin’ guy. Full disclosure– I feel like a little boy being sent outside to play in ’em. Growing up I was taught that men don’t wear shorts– it’s a macho thing. I know, I know. But if I was in shorts, I’d wear with a long sleeve sportshirt before I’d throw on a short sleeve. It’s just my way of keeping some self-perceived dignity, masculinity and balance. Ok, maybe there’s a third rule– a cool belt to punctuate the look.
John F. Kennedy (JFK) showing some great East Coast preppy style– the long sleeve oxford b.d. paired with Bermuda length chino shorts.
For cues on the proper wear of denim and short sleeves, there’s no better point of reference than the 1950’s counterculture. Guys had a style & swagger about them. They weren’t afraid to let you feel the weight of who they were. Some of the icons of those days had it too. Like James Dean, Chet Baker and Eddie Cochran–
And by the way– you won’t find any Playboys at our house. With all the kiddies, I’d hate myself if I ever walked in on a scene like this–