The Evolution of Style - Part 2

The Art of Being Well Dressed

The Art of Being Well Dressed

The Well Dressed Man


Ok, here’s where it gets challenging. Understanding that there is more to getting dressed than simply covering your body, that there is something about your choice of clothing that adds to your "person," and that it is neither vanity nor any weakness, but simply a celebration of just being a real, live man: these are the inner qualities that separate the men from the boys in appearance. We may not notice these qualities until we arrive at the type of venue which I've designated as Level 3. For it is not until we move a bit beyond sportswear that we begin to notice elegance.    

I became aware of the unsung awesomeness of The Well Dressed Man in what was a sort of personal epiphany. Having dinner in the Tap Room of the NYAC, I noticed a fellow, at a table across the room, who was wearing a patterned sport jacket, slacks, shirt and tie. Not much to it at first glance, but as I looked I realized that it all worked together. There was a harmony to the elements he’d chosen, a theme. The jacket was a dark, rusty-grey plaid; the trousers the right shade of dark brown flannel; the shirt had a little pattern to it, and a spread collar. He wore a dark silk knit tie and a patterned silk pocket square. An Ah-Ha! moment, there in the dim light of the bar. I realized in that instant that most guys would have no idea how to put that together; that the possibilities for costly error were so great that very few men would be willing to risk; and that to be willing and able to try to look like that took training, pride and guts. This guy, a total stranger, looked just great; a regular guy who had studied the art of looking good. Now this same guy, had he been in a perfectly tailored suit, custom-made shirt and expensive tie, would not have attracted my attention. The various elements of his coordinated outfit had been put together carefully. It showed real personal style. This guy was, obviously, more than the average man in a suit. He was a Well Dressed Man.







It’s not brain surgery. You may be color-blind or otherwise clueless, or just too concerned with the rest of your life to ever learn it yourself, but you could do worse than to have one of the great ones teach you. It’s better than going through life looking bad. In this do Alan Flusser’s books succeed. They are good guides – a bit dated now perhaps – to the right places to go to get your own style, whether a tutorial or a tune up.

A place like that is the quintessential Level 3 venue. A bit formal, but relaxed; dignified but not stuffy; a place where you might expect to meet a Well Dressed Man. In New York, particularly in restaurants and clubs, some in major cities, some in smaller ones, too, like Charleston, or Edinburgh, or Como. These are places that have Dress Codes, some written-out and specific, some just understood. There is no rule against wearing a graphic tee or a baseball cap at, say, Harry's Bar in Venice, but you'll definitely stand out if you do. And not in a good way.

Dressing at Level 3 is the next plateau, the sartorial bridge between average day-to-day and the more formal occasion which calls for a suit. This involves a lot of choices: maybe dress trousers, maybe chinos, maybe jeans; maybe a suit with just the right sport shirt (no tie); maybe a blazer; maybe a pattern jacket; maybe loafers, sneakers, oxfords. In short, Level 3 is where a man can be creative - or be lost. The possibilities for error are multiplied geometrically, and it takes some thought and some care, not typical characteristics of the hurried modern male.

“What?” you ask. “Better dressed in a sport coat and slacks than in my suit?”

That’s right. Better dressed because it’s harder, the way that climbing the face of El Capitan is harder than ascending Everest, because it demands more pure skill. And the ones who take the time and put in the effort to learn this skill are the ones who deserve – and get – the highest honors.

The difficulty most men will have with this Level 3 concept of dressing is getting the elements of it that work together, and the only advice I know to give men – besides telling them exactly what to wear with what, of course – is to tell them to go to stores they can trust. That’s all there is to it. Go into a store and look at the people who work there, and if you want to look like them, if you think the people working there have good style, shop there.