This salty sailor knows that attitude is everything-- what a great shot, one of my faves.
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.
The gents at the old Bobbie Brooks label provide a perfect example of how short sleeves can go horribly wrong-- Houston, we have a problem. Not even a notched sleeve can help that guy.
Yikes. See what I mean about the short sleeve & shorts look? This is an extreme case, but definitely makes the point that this can be totally creepy.
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–
James Dean definitely knew how to rock the short sleeve. Most of us are not James Dean material, so be careful-- or you could end up looking like a creepy handyman.
Chet Baker was no style slouch either-- shown here in a short sleeve shirt. And I can tell you right now, he ain't wearin' shorts.
Chet Baker wearing a short sleeve sportshirt in a shot from Bruce Weber's "Let's Get Lost"
Vintage Rockabilly short sleeve style-- Edie Cochran record shopping in the 50s.
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–
I subscribe to Playboy magazine for the great writing...
The Selvedge Yard 
Your two (and a half) rules are spot on.
I think the no short sleeves when wearing shorts rule is the most crucial of them.
The greatness of this post is its relevance to this time of year. When I see most short sleeve shirts I am often waiting for one of two things to happen: 1) the guy shows me his pocket protector 2) I get asked “do you want fries with that?”. ROLL ‘EM UP!
Don’t get me wrong, I do own a few s/s shirts but pull them out sparingly. It’s got to be good!
Starting out with a great shirt goes without saying, right Jimbo?
The most true statement I have heard (read) all night.
Foiled again.Darn.
Is one supposed to wear a long-sleeved shirt with shorts, then?
You can do what you want, but I would. JFK and many other preppy icons were/are known for this classic look. Heck, I have a picture of Ralph Lauren in a cashmere turtleneck & tennis shorts and he looks amazing.
Conjures up images of Al Bundy on the couch with his hand you know where. For the record, Homer Simpson probably did this best.
i started doing the long sleeve shirts and shorts last year and it added a dimension to my summer style that i greatly appreciated. i have this new selvedge chambray short-sleeve shirt that i’m having the damnedest time trying to figure out what kind of pants to wear with it. jeans seem a little cliche so i’ve been thinking about pairing it up with some full-cut linen pants.
Right On!
The only thing you missed was the complete inability for ethnic people to pull off the ss/shorts look without looking either like a tourist who’s lost their camera, or a FOB.
My Pops was a pretty cool cat back in the ’50s, and rocked the white shirt/chinos/slickedback pomp as hard as they came. Plus, he was a car club guy who owned part of a souped-up Cadillac as a teenager in Kamloops.
I do however, remember looking at one photo of him as a teen (when I was a kid in the 70’s) and distinctly remember him saying: “Ugh. I look like an immigrant from Shanghai. Or an off-duty NASA engineer.”
Well, ‘Duh’ Dad, you WERE an immigrant from Shanghai (and also an engineer), but that’s beside the point. Not surprisingly in that photo, he was wearing a white short-sleeved shirt with notched sleeves, a pair of high-waisted shorts, and high dark socks with brogues.
Ever since then, I’ve had a problem wearing shorts and short-sleeved button-down shirts, and NEVER together.
PS
I love this site.
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I actually had a dream I was gifted a chambray shirt I’m planning to purchase…in s/s version. It was borderline nightmarish.
I personally love the picture of Ralph Lauren (featured in the 40th Anniversary book) wearing cut off jean shorts and a black turtleneck sweater walking on the beach. I wish I was cool enough to pull that look off. I think unfortunately I would look less Ralph Lauren, and more Tobias Funke.
Polo shorts and shorts are acceptable – right?
That’s my question too. A lot of the polo shirts out there have arms that are too short and necks that are too big and collars that don’t lie flat. Colors and stripes often make the thing look hideous. Finding a good polo is difficult.
To each his own, of course, but I find this issue to be silly and the rule absurd: don’t wear short sleeve shirts and especially not with shorts. I also don’t agree that “attitude is everything”. This focus on men’s style is superficial at best. I suppose that because apparently JP makes his living in the fashion industry, he is a maven when it come to men’s fashion. Anyway, I’m gay and I find a homoerotic undercurrent on this site. The photos are mostly of men who in the gay scene would be deemed “butch” i.e. uber-masculine. The sailor glaring at the Playboy photo is particularly butch, but so are the bikers etc. Be that as it may, this is my first visit to this website and I think it’s very well designed and the pieces are knowledgeable and well-written.
I have to be honest, your commentary made me smile. Yes, talking about short sleeve shirts is silly in the grand scheme of life. I absolutely agree. And I am no maven.
I’m sure there is plenty of imagery here that one can deem as homoerotic. One man’s masculine is another man’s butch/gay….
To each his own~ as you say.
Thanks for the kind words on the site.
Best,
JP
Hi JP,
Thanks for posting my comments. I was surprised and pleased that you did so. Obviously, you are open to different opinions which is admirable….
I like very much your statement; “One man’s masculine is another man’s butch/gay.” It seems that “masculinity” is a continuum with straight at one end and gay on the other. Every man is unique and falls somewhere on that continuum….
I think that you are a maven, JP, of photography!! You have chosen excellent photos to post on this site to accompany your thoughts, feelings and opinions. So far, my favourites are James Dean lounging about wearing glasses and khakis, the 2 Beat buddies Jack Kerouac and Neil Cassady with their arms around each others’ shoulders and Neil Young and Stephen Stills circa 1970….
There’s much to see and think about on your site and I shall visit again.
Cheers
Lavalon
Ya I can dig me an ol’ short sleeve