Depending on where you live, shorts have a truly short life span.
Like Madras pieces, shorts are being stored deep within many closets until Spring arrives, soon to be replaced by an arsenal of hearty pants and trousers to accommodate the cold. Most people enjoy the shift from summer to fall as it gives them the opportunity to bring out tweeds and corduroy and other heavy woolens, and many more simply prefer the cooler seasons because of the plethora of sartorial choices now available as one can layer and bring out a variety of different pieces since the conditions are more temperate and comfortable.
Though, I personally prefer the warm weather, and more specifically, I love warm weather clothing. I obsess over summer fabrics: all of the various cotton weaves from seersucker, madras, and batik, to linens and silks, and even tropical and lightweight worsted wool for when things get formal. Being a lifelong Southerner – spending all of my years in Florida and Virginia – these clothes have become part of me. Hurricanes and a lack of seasons notwithstanding, I prefer what this climate affords me to wear, and a huge part of this is shorts.
This may be somewhat antithetic to my post on menswear becoming casual and comfortable as shorts are associated with the slovenly, the young, and the underachievers of the world who refuse to grow up and dress up. Surely most professional, adult men wouldn’t be caught in them unless the occasion warranted – be it for athletics or lounging. But shorts aren’t always bad, nor are they too casual. They can be both appropriate and cool, especially when you know when, how, and where to wear them.
If you look at the pictures above you’ll notice something: shorts have historically been a younger man’s game (and as I mentioned, are even today considered so). Still, don’t let that deter you. A young guy myself, I wear proper shorts somewhat frequently – often cotton and in various shades of khaki or gray – always with a button down, both short-sleeve and long (below is a typical get-up from me featuring a ’50s Brooks’ green/white uni stripe OCBD, no-name vintage khaki shorts, and Tretorn sneakers). Now, I certainly wouldn’t wear them to work, a formal dinner, or a first date, but like with everything else, there is a time and place. If you can wear sneakers to an occasion, surely shorts are not off limits. And it ultimately comes down to weather: as long it’s above room temperature outside, shorts can be standard kit if you do it correctly.
The old adage “keep it simple, stupid,” is perfect when it comes to clothes, and with shorts it’s no different. Cotton or cotton blends in any shade of khaki, gray, olive, or white work well with any and everything. I like to think of a good pair of shorts as miniature chinos, and as such, they’re just as versatile – you can wear them with a tucked in OCBD and penny loafers, or eschew any formality and simply go with a plain white T and canvas sneakers. Seersucker and madras fabrics, along with striped and plaid patterns, are also perfectly acceptable and work very nicely if worn with a subdued shirt. Regarding the dimensions, they should NEVER reach past the knee; depending on one’s height, any inseam length from 5″ to 9″ is suitable for virtually everyone and a higher rise is also immensely useful if you plan on tucking in your shirts.
To get the best idea what proper shorts are, look no further than the Japanese style book “Take Ivy.” It’s the perfect template with its classic and timeless pictures that capture the essence of “Ivy League” clothing at its height in the 1960’s. These young college students wore their shorts with EVERYTHING, even tweed sport coats, exemplifying how shorts – when worn correctly – are both youthful and proper.
It is hard to mimic ’60s cool of the dudes in these old pictures, but great shorts really aren’t that hard to find nor are they expensive. I’d recommend shorts from Lands’ End, Chubbies, and American Apparel. Some of the selections from each might be a tad ostentatious, but sort through that stuff and you’ll discover staples that’ll fit the bill. And to those who lament putting your shorts away: if you live in such an area that there are still warm days ahead, cherish such days and be sure to stave off doing so until you must.