With the change of seasons, the questions of course arise: For a man of a certain age—dignified, professional, reasonably successful in his career—what is the best hoodie to wear to a business meeting? Is the classic, yet simple, black tee as worn by Mark Zuckerberg or the late Steve Jobs still appropriate after Labor Day, and how soon must we substitute the turtleneck?

It has now been 50 years since John T. Molloy’s insanely influential Dress for Success was published, and it would appear that the instructions therein might no longer apply. Back then, Molloy told readers eager to climb the corporate ladder that a business suit was always a good bet, provided, of course, that’s what their superiors were wearing. Madison Avenue types—“creatives,” we might call them—“would be wise to avoid conservative clothing in favor of more flamboyant, fashionable and ‘with it’ gear.” That might be a sport coat with a pocket square, and loafers instead of wingtips. 

Critics, in Molloy’s own words, charged that he was “encouraging the executive herd-instinct,” and to this he pleaded guilty. In matters of clothing, “conservative, class-conscious conformity is absolutely essential to the individual success of the American business and professional man.” (A couple of years later, aware that there were “doubting Thomasinas” in his readership, he published The Women’s Dress for Success Book.)

Molloy’s advice, however objectionable to those possessed of an overly refined social conscience, was informed, he insisted, on empirical research. He wasn’t just spouting his personal opinions. He was reporting the findings of “wardrobe engineering,” as he called it, using that day’s equivalent of what two decades later were known as “focus groups.” His conclusions were “data-driven.” This was science—you know, like Sir Isaac Newton and Bill Nye.

Such research would reveal something else today, of course. Casual Fridays were an early gate on the slalom-like descent that was to come, propelled farther and faster downhill by Covid, work-from-home arrangements and Zoom meetings. By this time, Silicon Valley entrepreneurs were at the top of the heap, determined to show that they were not the Man in the Grey Flannel Suit, but something bold, informal, edgy. Now everybody seems to follow their lead—except maybe a true rebel who might flaunt convention by daring to show up at a business meeting in a necktie and button-down shirt. Fetch the smelling salts!

Fashions come and go—that, after all, is what fashion means—so this surely cannot go on forever. But how much more casual we can get is worth asking.  “Clothes make the man,” Mark Twain said. “Naked people have very little influence on society.” We might well find out that this is not the case. There are still limits, at least for now. Letting it all hang out did not advance Jeffrey Toobin’s career, though future generations might see him as a trailblazer. Statues in his honor might one day appear near the Lincoln Memorial, around which media executives with their pants around the ankles gather to pay homage.

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And why should any of us care? G.K. Chesterton, by no means a dandy himself, notwithstanding his cape, swordstick, and pince-nez, believed that our clothing choices matter and offered a characteristically thoughtful explanation. Chesterton suggested that it might not be possible to be “completely human without clothes,” as Adam and Eve themselves were to discover. Clothing is “the symbol of purely human things; of dignity, of modesty, of self-ownership, of property, and privacy and honour.” 

Even in the “purely artistic sense,” Chesterton observed, we would “never have become human without [clothes], because the range of self-expression and symbolic decoration would have been hopelessly limited, and there would have been no outlet even for the most primary instinct about colour and form.” 

All of which is true, raising obvious questions: What does a tee shirt, hoodie or sweatpants symbolize, especially in a business environment? And could the creationists be mistaken? Are we really descended from apes, and have now begun to make our way back to mucking about on all fours? Check back in a few years, if you have the stomach for it.