I was discussing the history of style with Alan Flusser in his office on East 48th Street in Manhattan, a convivial nook that shares the floor with his showroom and workroom. I turned to a topic about which I knew, from Mr. Flusser’s informative writings, that he had much to say: how it is that the typical American businessman or professional man used to look so natty and how is it that his descendants came to look—rather as they now do.

“First of all,” Mr. Flusser told me, “in between the wars, you had a situation in which a lot of people couldn’t afford clothes. It was the Depression. On the other side of it, there were still a lot of wealthy people. And there was also Hollywood, and in Hollywood at the time, when moviemaking was at its zenith of popularity, you had great male leading actors whose job it was to project Hollywood glamour, not just on screen but in their social lives.”

Anyone so young as to wonder if celebrity worship started with iPhone apps and social media should read a good history of American popular culture to know what Mr. Flusser means. My mother, a spiritual child of the Golden Age of Hollywood, grew up hoping to copy every button and bow on her favorite stars and still sees actors as transcendent personalities. For men, however, as Mr. Flusser went on to note, the catalyst was a “confluence of male sartorial role models,” from British aristocrats, politicians and businessmen to those movie stars. Men were taking an interest in dressing well, in part due to those examples, which were regularly offered in the new media of film, picture magazines and, later, television.

“In Hollywood at the time,” continued Mr. Flusser,” you had about twenty men who individually set their own kind of style” and thereby marked the path for those millions interested in following. He noted in particular Cary Grant and Fred Astaire. “In terms of learning how to dress, there developed between the two world wars the kind of clothing that we wear today, soft clothing that you could move in comfortably—lounge clothing, it was called—not stiff and Victorian.” Indeed, although the modern business suit’s origins can be traced back to nineteenth-century military uniforms, it was the resulting lounge suit of British gentlemen that evolved into the contemporary international business suit. (If you do not believe that, put on a suit of the London cut, turn up the collar and pull the lapels toward each other. You will look just a bit like the Duke of Wellington.)

That is all well and good, but who in the public eye right now would a young man seek to emulate? Attention, Millennials, this one is for you: “I would be hard-pressed to come up with a single person,” said Mr. Flusser, a note of frustration overtaking what had been an assertive tone. He suggested George Clooney, who is not in his first youth, of course, but did not feel comfortable naming anyone else in entertainment.

As I now knew was his method, Mr. Flusser offered history: “In the 1960s, you had the Peacock Revolution. There was a rebellion against ‘the Establishment’ and the more traditional dress that people associated with their parents. From about 1968 until the 1980s, there was a void of good guidance on how men should dress. If you take the generation after that, you get pretty close to where we are today, and you find two complete generations of men who never had the benefit of having any kind of solid information on the elements of stylish dressing. By then, you had had a complete inversion. Instead of style being handed down from above, it bubbled up from below—from the street.” And street wear, as we know, makes its mark by aspirating toward a state of cool—a hard state to reach and an even harder one to maintain.

Where does that leave us now? “It’s a very confusing period of time in terms of trying to learn how to dress and come to terms with what you know about how to present yourself,” concluded Mr. Flusser. True enough, but at least, because of our conversation, I had come to understand why that is so.

Credit:  Alan Behr

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