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The caption of this November 1936 illustration reads,“This on-the-spot sketch of Riviera resort fashions, quite aside from its obvious decorative ping, has its uses as a check-up on prevailing plage fashions, because our southern resort fashions follow those of the Riviera almost as closely and as constantly as lunch follows breakfast.”

Leafing through the fashion spreads in current issues of Esquire, it seems that the modern, well-dressed man has three things on his mind: the acquisition of vast fortunes, the seduction of slender women and a sense of superiority based on his casual outlook and ability to purchase a whole host of consumer goods.

In these pursuits, though, he is bitterly at odds with the members of his grandfather’s generation, the well-dressed gents of yesteryear, who, as depicted in much older editions of Esquire, wore tweeds with deliberation, silks with panache and didn’t seem so concerned about such contemporary piffle as the exotic surnames of fancy designers.

A look through the Esquire archive proves this point. From its inception in 1933, Esquire presented its readers with lavish illustrations of gentlemen in stripes helping striking ladies out of cherry-red roadsters and offered accompanying texts with reflective reporting that analyzed the latest fashion trends as carefully as one would examine the arenas of politics or ideas. In these early spreads, prices were never mentioned, nor were there any lists of where to purchase the pictured merchandise.

Today, however, a man can expect no such objective depth or pleasure from his fashion magazines. Instead of illustrations suffused with equal parts imagination and just-the-facts journalism, he is assaulted by page after page of slickly composed photographs that aim not to educate him in the ways of the hand-felled collar or the hacking pocket but rather to emphasize price tags, trendy labels and the army of merchants standing at the ready throughout the world, all awaiting his cash.

To be sure, men’s magazines have always had money on their minds; even in that aforementioned golden age, Esquire was stuffed with swanky advertisements and editorial references to exclusive haunts and hunting grounds, from Long Island’s Meadowbrook Country Club to sprawling ancestral estates in England. But in the decades since the Thirties, Forties and Fifties, men’s magazines have undergone an important transformation, abandoning their role as recorders of the tastes and rituals of the lucky few and reinventing themselves as conduits directing anyone with a few spare dollars in his pockets to the nearest outpost of some corporate luxury purveyor. This change was not necessarily the magazines’ fault, for as the readers they served abandoned coded dress for complicated occasions in favor of a more easy, “anything goes” mentality, magazines by and large followed suit in order to stay relevant. Rather than reflecting some ominous alliance of the editorial and advertising departments, this shift had perhaps more to do with the rise of mass-produced, ready-made clothes and the resulting commoditization of taste and style.

There are some who celebrate this and similar upheavals, seeing in the evolution of these once-exclusive magazines the triumph of a democratic revolution in taste begun in the Sixties. Now, they say, fashion comes from the streets, requiring not an educated eye and careful planning but only an impassioned, personal style that is free from the rigid constraints of aesthetics and propriety. Out went the forward pleats, belted backs and dashing homespun plaids, in marched distressed denim, vintage tees and an international look at home nowhere and everywhere at the same time.

The illustrations and captions that follow, culled from the Esquire archives, serve as relics from a bygone age in which Esquire referred to itself with a wink and a smile as the indulgent “Uncle Esky,” and aimed its reporting at readers’ eyes and minds rather than the seats of their lust and ego. We present the old illustrations here not to nostalgically lament the passing of some gentler age—because it was far from gentle—but to remind us of the truly meaningful and pleasurable way in which style was once explored and reported.

“Please pardon the digression,” begs the caption of a November 1934 illustration (titled “A Portrait of Happy Hunting Horse”), “but of the three grins on this page we think that of the horse is much the best.” These three illustrations, all from a single series published in an early issue of Esquire, represent the three main modes of dress at the time: town, country and evening. The three spheres required a complete set of clothes necessary for the well-dressed man’s varied endeavors as well as a proper grasp of the correct tone and spirit appropriate for each.



Nowhere is this more obvious than in the illustration of the party scene, which informs the curious reader not only of the latest trend in tailcoats but also of its equally privileged provenance: the outfit, reads the caption, “seems to have been influenced a great deal by the ideas of the tailor who makes evening clothes for the British royal family.” In an age when fashion filtered from the top down, such regal distinctions implied permission for the American gentleman to dress accordingly.


By the Fifties, Esquire had abandoned the hand-made fashion illustrations of the two previous decades and printed color photo spreads in their places. Still, the Esquire world was ruled by the same logic that had governed it in decades past, with the lush, carefully choreographed tableaux vivants now played out by real-life models. But the Esquire man, unfailingly swathed in the tailored mantle of power, would soon be replaced by a vastly different style icon. As Esquire continued to propagate a vision of men in suits ruling the world and calling the shots, Marlon Brando, James Dean and their ilk dared American males to ditch the suit and don, instead, jeans and t-shirts.

The new style went against everything the magazine had stood for, and in the March 1956 image below (titled “Men at the Top”), the figure most representative of the future of fashion, the denim-clad worker, receives only a single, dismissive line: “The man waiting for the decision wears a hat that is splendid for deflecting rivets.”


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