Aaron P. Bernstein / Reuters

Recently, a Facebook ad tried to sell me a monocle. The ad probably appeared because I had visited too many over-specialized menswear websites. It showed an earnest young man with a full beard, waxed mustache, period clothing, and the anachronistic piece of eyewear. He looked ridiculous.

Why would anyone want this? I’ll admit to owning a tweed blazer (or seven), but when it comes to retro men’s fashion accessories, monocles are on another level of affectedness. They look strange, too. One eye is magnified and obscured, while the other looks naked. A monocle perches on the face, precariously unsupported, requiring effort and practice just to keep it in place.

In the present day, a monocle is almost always part of a costume. It’s a visual shorthand for a stock character: a wealthy gentleman with the air of a Gilded Age aristocrat ready for a black-tie gala or a night at the opera. He peers through its single lens to project a critical gaze at a work of art or perhaps a raffish orphan given into his care. It drops from his eye to mark astonishment at a breach of manners or an abrupt revelation. Or else, the monocle-wearer is a sinister European gentleman. Aristocratic, yes, but cold and calculating, filled with menace.

Joseph Chamberlain wore one. So did Woodrow Wilson and Otto von Bismarck. Joseph Conrad had one, as did Yeats and Auden. The villainous Penguin fights the Batman wearing a monocle. The Monopoly Man, Rich Uncle Pennybags, ought to have one but doesn’t. But the plutocratic legume Mr. Peanut is never seen without his, nor is Eustace Tilley, The New Yorker’s cartoon mascot.

This little glass disk designed as corrective eyewear wound up as a comic prop, a universal metonym for wealth and snobbery. Monocles were briefly stylish at first. But they were never cool.

The magnifying properties of glass have been in use for millennia, and wearable since at least the Middle Ages. The first spectacles appeared in Europe in the late 13th century. By the early 17th, Galileo had his telescope. The sextant sailors used in the 18th century for celestial navigation had a telescopic attachment (which gave Popeye the Sailor his characteristic squint). Around the same time, a single lens on a little stick appeared, called a quizzing-glass.

The monocle followed. It was fixed in the eye socket and held in place hands-free, wedged behind the loose skin around the eye thanks to the orbicularis oculi, the muscle that closes the eyelid. Its advent is usually associated with Philipp von Stosch, an 18th-century German baron, who in his time was better known for writing the definitive work on carved gemstones and living an active, open life as a homosexual. Notwithstanding, popularizing the monocle became his lasting legacy. By the end of the century, it was in use all over German-speaking countries. It jumped to London around the turn of the 19th century, where it took hold among the aristocracy.

This period, the Regency era, was ground zero for British dandyism. Men cared how they dressed. Attire became a language of status. Older aristocrats wore monocles; younger and poorer men copied them. They were explosively popular, and why not? In its brief heyday the monocle was an attractive little object, round or octagonal, rimmed with silver or gold or horn, fixed to one’s coat by a silken ribbon. It was even useful for looking at things.

But by the middle of the century, monocles had already become a comic staple. Cartoons of the period show caricatures of self-regarding young fops posing and preening with their monocles on full display. In Little Dorrit, Charles Dickens lampooned a character unable to hold one, because he “had such flat orbits to his eyes and such limp little eyelids that it wouldn’t stick in when he put it up, but kept tumbling out against his waistcoat buttons.”

By the start of the 20th century, the monocle gag was already tired. In 1925, The New Yorker put a monocle on its mascot—the guy in the high collar looking at a butterfly, created for the magazine’s inaugural cover. The joke (which doesn’t land as well today as it used to) is that the overrefined urbanite preens in curious contemplation of the butterfly, his affectation thrown into relief by nature’s unpretentious beauty. New Yorker readers were supposed to see that this guy is a poser, making them feel like the real sophisticates.

Monocles were the sign of a man hoping to appear to be what he was not: the young hoping to seem mature; the vulgar hoping to seem tasteful; the petty longing for higher status. But that implies the monocle had a moment when it did look cool, leading so many people put their faith in it. If so, that brief instant of Peak Monocle has been lost to history.

Monocles returned to use in the early 20th century as a must-have accessory among the military officers of World War I. Although the eyepieces were worn by soldiers on both sides, the German High Command played the biggest part in reviving them. Members of the Prussian nobility, a German state with a long military tradition, seem to have been completely unaware of the monocle’s history as a comic prop, occupied as they were with their irony-free lifestyle of horsemanship, saber duels, and gymnastics.

In their official portraits, members of the German High Command make monocles seem quite frightening. Wartime propaganda picked up on the signature accessory, deploying it in caricatures of an archetypical German baddie. That image became the progenitor for all the monocle-wearing villains of the 20th century, from Colonel Klink in Hogan’s Heroes to the Marvel Comics scoundrel Wolfgang von Strucker. The vampire muppet Count von Count wore one, and it added to the menacing look of Star Trek’s militant metaspecies the Borg.

The monocle’s first two lives, as foppish accessory and evildoer’s adornment, have persisted into the present. But the apparatus’s last serious vogue, in the early 20th century, is almost entirely forgotten.

As a rule, monocles were a male accessory: If in need of an aid to vision, a woman would use spectacles or a lorgnette, a pair of glasses on a handle. Because the monocle was so strongly gendered, it became a low-key mode of cross-dressing. Trend pieces of the period treated it as a fad—What have those flappers done now?—but it was also taken up by the lesbian community in Montmartre, Paris. In the center of a 1930 photograph of a Parisian nightclub crowd, a woman in tuxedo and cigarette holder flashes her monocle directly at the camera. The gesture seems to carry both a foppish sophistication and a Prussian coldness. This is high fashion, but it is also daring defiance.

Worn in a woman’s eye, the monocle makes an unexpectedly forceful statement of transgression. For once, it isn’t funny in the least. A man in a monocle is putting on airs: He wants to be taken seriously, elevated to a status that he might not hold, but that someone of his sex could. A woman in a monocle doesn’t aspire to be what she isn’t; rather, she takes what she shouldn’t.

An echo of the Montmartre monocle reverberates in Madonna’s 1989 “Express Yourself” music video. Directed by the then-27-year-old David Fincher, it was at the time the most expensive music video ever made. For the first two minutes, Fincher plays things relatively straight—in a Fritz Lang noir world, men wear monocles and Madonna wears glamour couture. Two minutes in, Madonna reappears wearing a double-breasted suit and monocle, advancing straight toward the camera. The 1930s are eerily resurrected, in form and content. Madonna reminds the viewer that you don’t have to accept what you’re given: Don’t go for second best, baby.

That was probably the last time a monocle was at all cool, maybe the last time it ever will be. I could get one now for about $70, in gold or black or silver, and wear it in the hopes of seeming rakishly authentic to an old-world elegance unjustly forgotten. I’d probably look like a twee jerk instead. Even riding an electric scooter or wearing Google Glass eyewear would seem more stylish.

The monocle evokes not just wealth but a nostalgia for an imaginary Gilded Age. It longs for the airy sophistication of a genteel upper class, who were the harmless if easily exasperated bearers of elegance and high culture. By contrast, today’s extremely wealthy are almost aggressively banal in their self-presentation. The billionaires in Silicon Valley (or at Sun Valley) wear jeans, polo shirts, and fleece vests. They listen to rock bands, not string quartets. Perhaps being that wealthy requires a certain lack of imagination. Perhaps any hint of an inherited aristocracy might interfere with the myth that today’s superrich rose from the ranks of the commoners through talent and plain hard work.

Maybe it’s better this way. Imagining the very rich as overbred aesthetes who can be undone by hearing a rock-and-roll song or being served an inferior Montrachet makes them seem too refined and unworldly ever to have done the things necessary to make all that money in the first place. To imagine the monocle as a symbol of upper-class sophistication just makes the device seem charming and innocent, which risks erasing the frequently un-charming, if not actively bloody, history of where great fortunes actually come from.

So maybe this is the real joke: When the monocle falls from the eye in astonishment, it’s really a wink at the open secret of where wealth actually comes from. If monocles were never all that cool, maybe it’s because rich people weren’t either.

This post appears courtesy of Object Lessons.

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