Don't let the innocent faces fool you; I'm fairly certain a few cherry bombs had just been lit in the bathroom.

I recently discovered a cache of photographs dating from the mid eighties. They are of me and friends or family, and because film still had the aspect of being finite, the settings are limited to special occasions—weddings, birthdays, graduations. I was an active young boy; things like tablets having not yet been invented, I instead played in the woods and grappled with friends. Dressing for special occasions did not prevent me from these pursuits, however, and I recall a persistent tension between being in good clothes and wanting to, say, organize a bonfire. Precisely because of that tension these photographs are a source of inspiration, and in studying three in particular, an enviable authenticity reveals itself.

The first photograph finds me and a friend on a boat in the Hudson River. It is a wedding and I am appropriate in a navy suit. A red and gold foulard is snugly cinched into the collar of a white shirt, but otherwise left askew and flapping. A lapel folds and hair is anything but smoothed. My friend, a more adventurous spirit than me, stares into the camera, challenging the viewer to say something about his choice of odd jacket and navy trousers for so formal an occasion. That the jacket is double breasted and carries a jaunty check reinforces his cocktail-wielding swagger. The lesson couldn’t be plainer: actual dishevelment is superior to artful dishevelment. Only the most tedious dresser would intentionally cause a tie to flap or permit a little thing like propriety to ruin his evening.

I am maybe a year older in the second photo, and, perhaps influenced by the Welsh countryside that is the setting, more casually turned out. My cousin and I are on our way to an outdoor school function—an ideal setting to this day for the dependable navy blazer and tan trouser combinations we both have chosen. A closer inspection reveals rich detail. My jacket is a low-slung four-on-one double breasted, a style named after the man who popularized it—The Duke of Kent. I wear it brazenly unbuttoned. My cousin tucks his tie into his pants. My boutonniere is set at a rakish angle. A penny-loafered foot juts out beneath rumpled chinos revealing white socks. Refusing to fuss over one’s clothes takes real restraint, or, as is the case when eleven, truly not giving a whiff. Sadly, today I do care; I actively resist smoothing lapels and adjusting ties. If I could only have retained the nonchalance of my youth.

The third and last photograph is the most causal look, and I will begin with the obvious lesson therein: active wear should be made of rougher materials and with durability in mind, but no less coordinated than more formal clothes. Casualness is not an opportunity for slovenliness, or, as is often the case, colorblindness. To wit: blue-on-ivory check flannel shirt, navy cable-knit sweater vest, regimental ribbon belt, pale blue needle cords. Ideal clothes for whatever mischief the weekend promises.

To be truly inspirational, the confluence of dress and activity must be genuine. I see too many kids parading around in carefully conceived “outfits” today, playing the part but ultimately too concerned with scuffing their special edition athletic shoes. Ask yourself—what’s cooler: a kid dressed as a skater skating, or that same kid, following some event, hitting a rail in chinos, blazer, tie and penny loafers? This is, of course, well understood in cinema. The same principle has Cary Grant in a suit dodging a crop duster, or any number of Bonds actively ruining a dinner jacket. There is style in treating one’s clothes as clothes rather than rare possessions, but we adults can only hope to do it with the abandon of a child.