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Fear of Fashion | The Point Magazine

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On the internet today, discussions about men’s fashion flourish in every digital corner about practically every imaginable aesthetic: from subreddits echoing with conversations about 1960s Ivy Style to forums deconstructing the complexities of Rick Owens and the Japanese avant-garde. In private Discord and Slack channels, men discuss how to create the perfect outfit, while TikTok and Instagram accounts buzz with fashion-forward videos and outfit showcases. Even in unrelated territories, such as the tech-centric realms of Hacker News and number-crunching circles of accounting Facebook groups, people opine about how to dress for the office.

I first became acquainted with this world in 2007, when a woman for whom I long harbored a secret crush invited me to be her plus-one to a wedding. Having built the day up in my mind, I felt I needed to find the perfect suit to make an indelible impression. So, like any diligent researcher, I went online. In my search, I stumbled upon Styleforum, the largest and longest running online forum for menswear enthusiasts. My fascination with tailoring wasn’t new—I was already drawn to the sleek aesthetics of mid-century jazz musicians and the modish cool of French New Wave cinema. But it was on Styleforum where my early taste for trim suits, drainpipe trousers and skinny black ties found new depths. It was here that I learnt the technical tailoring intricacies that would later enable me to write about clothing for a living and amass an audience of over half a million followers on X, the social media site formerly known as Twitter. On Styleforum, there were posts about 1930s drape cuts, Milanese buttonholes, pad stitching, extended front darts and the contrasts between Savile Row and Neapolitan tailoring. In threads titled WAYWT (What Are You Wearing Today), members posted photos of their daily outfits (colloquially known as “fit pics”). No matter what style they sported, the photos had one thing in common: they all blurred, cropped or blocked out their face, giving the poster a curious veil of anonymity.

Nearly sixty years ago, Tom Wolfe laid bare a fundamental truth about men’s relationship to clothing that still holds today: talking too much or too deeply about clothes is taboo. “It’s the secret vice!” he exclaimed in a 1966 essay published in the New York Herald Tribune. Wealthy and powerful men, he observed, were obsessed with functional buttonholes on the sleeves of suit jackets and sport coats—a detail that, at the time, suggested the garment was handmade and likely bespoke. With “marginal differences” like these, as Wolfe called them, wearers could telegraph to a small subset of people that they had a keen eye for detail while allowing their interest to remain nearly invisible to the general public. In the world of high-end men’s tailoring, everything is coded: a shirt with a flapped breast pocket (J. Press) versus a shirt with an open breast pocket (Brooks Brothers), a lapel finished by machined edge stitching (American) versus a lapel finished with handmade pick stitching (British, Italian), a soft shoulder line (Naples) versus a structured one (London), and so on and so forth.

Such details were a wink and a nod at the cognoscenti, but they were not an invitation for conversation. “At Yale and Harvard, boys think nothing of going over and picking up a copy of Leer, Poke, Feel, Prod, Tickle, Hot Whips, Modern Mammaries, and other such magazines, and reading them right out in the open,” Wolfe wrote. “Sex is not taboo. But when the catalogue comes from Brooks Brothers or J. Press, that’s something they whip out only in private.” Even men gripped with a mania for bespoke tailoring were too embarrassed to discuss their interests with others.

Although everyone participates in fashion, men shirk from being too closely associated with it. But why? One reason, perhaps, is that taking a strong interest in clothing has been historically coded as frivolous and feminine. To be sure, all men are conscious of fashion to some degree—if given a choice between pink and blue jeans, they will have a preference based on what they think each color telegraphs—but they fear being seen as too clothing-conscious, possibly because they believe it will diminish their masculinity. This is the trap that has defined male style for the better part of two hundred years: for a man to look good, he must not look too much like he wants to look good. Indeed, the Italian term sprezzatura, or “studied carelessness”—which originally appeared in Baldassare Castiglione’s 1528 The Book of the Courtier, where it was used to discuss political etiquette—constantly pops up in menswear writing. The art of style, it seems, is about looking as though you accidentally fell into an outfit, straight from bed or the gym.

This idea is rooted in a long-standing bias against fashion. As the fashion scholar Rhonda Garelick noted in the New York Times, Western philosophers derided fashion for millennia, using it as a “symbol for every manner of human weakness: duplicity, depravity, narcissism, frivolity, greed—attributes also ascribed traditionally to women.” In his Discourse on the Arts and Sciences, Jean-Jacques Rousseau inveighed against clothing that rose to any level above pure utility, arguing that gilded finery stoked covetousness and sapped virtue from ethical men. “The good man is an Athlete who delights in fighting naked,” he asserted. “He despises all those vile ornaments that would hinder his use of his strength, and most of which were invented only to conceal some deformity.” Some went so far as to assert that fashion is antithetical to good taste: Kant argued in his Critique of Judgment that our views of beauty should never change as long as we have common sense.

Within this tradition, men were to live a life of the mind or a life of action, with little concern for frippery. Yet there have been periods when men took great interest in clothes and wore bright colors, elaborate shapes and sumptuous materials. After Napoleon took power, members of the French court ditched their more casual English attire and revived the elaborate habit à la française of Louis XVI’s reign. Aristocratic men wore a version of the three-piece suit: a long silk coat decorated with exquisite floral embroidery, which they paired with a light-colored waistcoat (also elaborately decorated) and dark knee-length breeches. At the other end of the social spectrum, Charles Baudelaire wore velvet-collared coats and giant bow ties. For this French poet, fashion was more than a frivolity; it was a form of art that captured modern life’s ever-changing spirit. In those transitional periods when the aristocracy had been weakened but democracy had not yet become hegemonic, the dandy represented a new kind of aristocrat, marked not by birth but by taste. Baudelaire described dandyism as the “last flicker of heroism in decadent ages.”

Most notable among these dressers was Beau Brummell, a British arriviste widely considered to be the first dandy, who wriggled his way into high-society circles in the Regency era using nothing but his discerning sense of taste. Brummell’s approach to fashion was revolutionary in its simplicity and refinement at a time when European men’s clothing was characterized by extravagant colors, rich fabrics and intricate embroidery. With his uniform—a dark coat worn with full-length trousers and a meticulously tied neckcloth—he championed the idea of understated elegance, a concept grounded in fit over flash, sobriety in color and cleanliness in grooming. This was epitomized by what he called the “dandy’s pose,” which paired an eye for detail and an elevated sense of taste with a seeming detachment toward all things, suggesting to the viewer that the dandy’s sense of aesthetics was innate and effortless. “If John Bull turns around to look at you, you are not well dressed; but either too stiff, too tight, or too fashionable,” he famously said. Brummell’s no-frills approach to clothing, though iconoclastic in its time and demanding scrupulous attention to one’s wardrobe, set in motion a new kind of sobriety that would define modern male attire (where Brummell wore a dark coat with white breeches, a similar look today can be found in the modern business uniform consisting of the navy blazer with pearl gray or tan trousers).

If Brummell gave us a new sober template for male fashion, Oscar Wilde gave us our stereotypes. The Irish playwright was more than your average clotheshorse—his fascination with the emotive impact of personal appearances breathed new life into the dandy’s pose. Where Brummell’s formulation of the dandy emphasized the virtues of restraint over foppish excess, Wilde’s version was all about flamboyance that shined out from one’s inner character. In his college days at Oxford, Wilde dedicated himself to sartorial spectacle, donning loudly checked suits and bowler hats against a backdrop of august lecture halls and horse-racing tracks. Soon he was flaunting long hair, velvet suits that whispered of Renaissance grandeur and cravats tied with a poet’s nonchalance. His distinctive look caught the eye of caricaturists, earning him a reputation as the “Professor of Aesthetics” in satirical magazines like Punch. Like a Victorian-era Kim Kardashian, Wilde was a master at spinning controversy into gold. During his promotional tour for the operetta Patience, he dialed up his attire, sporting breeches, stockings, elegant pumps, fur-lined overcoats, billowing cloaks and colorful cravats, which would prove to be an ingenious marketing strategy. His every appearance was a headline.

But his fame took a dark turn in 1895, when he was brought to trial on charges of gross indecency—a severe accusation in an era when the mere rumor of homosexuality was enough to ruin lives. In a dramatic conclusion, Wilde was found guilty and sentenced to two years of hard labor. Historians have written extensively on the supposed connection between homosexuality and a male interest in clothes, but it was the trial of Oscar Wilde that most prominently etched the connection between sexual identity, social class and sartorial flamboyance into the public consciousness. To this day, gay men continue to be cast in the Wildean mold: witty aesthetes and connoisseurs of the arts leaning toward “effeminate” interests like fashion.

This stereotype exerts such a strong influence that even today, straight men can feel a distinct unease about indulging in the Wildean practice of self-styling. The prevailing attitude is that “real men” are too grounded, serious and rational to concern themselves with such trivialities. Indeed, since the suit emerged in the twentieth century as a symbol of conformity, men who diverge in their fashion choices are seen as setting themselves apart. In his book Cultures of Masculinity, sociologist Tim Edwards writes: “Fashionable, image-conscious or simply ‘dressy’ men are often seen to arouse anxieties in gendered as well as sexual terms, being perceived not only as potentially gay or sexually ambiguous but as somehow not fitting in, particularly in terms of rumbling any wider belief in masculinity as a form of profoundly ‘un-self-conscious being-ness’ or in undermining the notion that ‘real’ men just throw things on or just are men.” And yet, the male interest in clothing persisted—just in secret.

Of course, there have been some bright spots over the past hundred years. In the 1920s, a group of young bohemians known as the Bright Young Things—which included luminaries such as Cecil Beaton and Evelyn Waugh—reveled in fashion. They threw fabulous costume parties, gallivanting through nighttime London in Georgian-era attire, sailor outfits and bespoke evening wear while treasure hunting and going to endless afterparties. In the 1960s, young Brits electrified by rock ’n’ roll wore collarless jackets and psychedelic clothes from the famous Kings Road boutique, Granny Takes a Trip. Their American counterparts, the hippies, embraced flared pants, floral shirts and platform shoes. Iconic Savile Row figures Tommy Nutter and Edward Sexton dressed the era’s rock aristocracy, merging traditional craftsmanship with the fashion of the day. Still, the male fear of fashion became ever more entrenched as the twentieth century wore on. With the decline of tailored clothing and the rise of casual comfort, the uniform of the middle-American male, by the turn of the millennium, was nothing flashier than a polo and khakis. The aesthetic bleakness of late-twentieth-century fashion only made it more difficult for men interested in aesthetics to hew to Brummell’s ethos of the well-dressed man. By wearing anything other than a pique polo with flat-front khakis, one risked looking effeminate, gay or simply like a try-hard. Brummell would have never imagined a bar so low—but in his terms, they were spoiling the dandy’s pose of looking effortlessly stylish.

In the early 2000s, however, things started to change. First, self-fashioning men, many based in urban centers, started to take a more explicit interest in grooming, buying hair serums, expensive moisturizers and scented shaving gels. They bought slim-fit clothes, some even raiding the women’s aisle for skinny jeans at a time when such silhouettes were not available for men, and loaded up on fashion magazines. The press, with no little anxiety, popularized the term “metrosexual” to describe this new consumer group. Although Mark Simpson, a gay writer, first coined the term in the 1990s, it was now being used to call into question the sexuality and masculinity of men who were bucking traditional gender norms. In 2003, just as it was starting to gain mainstream traction, Warren St. John wrote in the New York Times: “Along with terms like ‘PoMosexual,’ ‘just gay enough’ and ‘flaming heterosexuals,’ the word metrosexual is now gaining currency among American marketers who are fumbling for a term to describe this new type of feminized man.” An East Village graduate student quoted in the story defended his love for Kiehl’s lotions and Diesel jeans by saying, “It doesn’t bother me at all. Call it homosexual, feminine, hip, not hip—I don’t care. I like drawing from all sorts of sources to create my own persona.”

Meanwhile, another fashion trend was brewing: the “heritage movement.” Traditional menswear items, such as raw-denim jeans with neatly upturned cuffs, buffalo-check flannel shirts and Horween leather work boots, emerged on the streets of New York City and San Francisco, albeit in slimmer silhouettes. At first, early adherents to this style were still often labeled “metrosexual.” But unlike the more polished designer styles pushed by magazines like Details, these outfits took inspiration from idealized masculine archetypes—the factory worker, the New England hunter, the Northwestern lumberjack, the mid-century New York advertising executive. This thick layer of nostalgia for traditional masculinity gave straight men a protective cover for exploring their interest in clothes. They were not vain; they were investing in timeless classics once worn by their grandfathers. They were not interested in fashion; they were dressing like grown-ups. Upscale boutiques with names like “Unionmade” sold trendy clothes laden with masculine references, such as chambray shirts with runoff stitching and hunting coats with ammunition-ready pockets. When J. Crew debuted their Liquor Store in 2008, they transformed an after-hours watering hole into a menswear-only boutique that evoked a 1960s conception of gender roles. Dimly lit rooms were covered in plush leather chairs, oriental rugs and wood paneling. In the corner of one area, a bookshelf was stacked with Strand-issued classics—Kerouac, Hemingway, Cheever. Thick cashmere cardigans were draped over Globe-Trotter suitcases, striped rep ties rolled into lowball glasses. Once made for loggers, carpenters and longshoremen, the preppy clothier was introducing these blue-collar styles into white-collar offices, often bought by men who wanted a safer entry point into fashion.

At the same time, an online ecosystem emerged that allowed men to experiment with fashion in the privacy of their home. Men’s style blogs such as The Sartorialist, A Continuous Lean and Ivy Style—along with the many Tumblr microblogs that emerged in the late 2000s—gave men endless inspiration for how they could dress. On forums such as Ask Andy, Superfuture and Styleforum, where I got my start, men could talk about clothes and post photos of their outfits without revealing any personal information—or risking having their masculinity called into question. At Styleforum, there’s an ongoing “Should I Buy” thread—essentially the online, anonymous version of pulling something off the rack and asking a friend’s opinion. On WAYWT posts, men upload photos of themselves to get opinions on how they look, typically with their heads cropped out or faces obscured by a black circle.

These digital veils aren’t the only defenses used to guard against the vulnerability of seeking affirmation from other men. A curious new type of language has also emerged in these spaces. Here the act of shopping is recast in man-of-action metaphors, such as “pull the trigger,” “take the plunge” and “investing.” Some men will try to rationalize their clothing choices—a hat is necessary for the weather, a suit is worn for respect, putting on a tie is simply something grown men do. And male interest in fashion often takes the form of “collecting” or connoisseurship (e.g. watches or sneakers) or utility fetishization (e.g. “everyday carry,” or EDC), rather than what might be seen as more feminized forms of self-styling or vanity (horror of horrors!). By framing their choices in these ways, men can argue that their decisions are guided by rational principles, such as practicality and maturity, rather than aesthetics.

Today, the younger generations are coming to fashion with considerable openness and much less of the sexual anxiety that has marked male interest in fashion since Oscar Wilde’s time. Many Gen Zers are aware of brands such as Balenciaga, Saint Laurent and Supreme, and they follow influencers such as Wisdom Kaye (who has more than ten million followers on TikTok). They’ve grown up with celebrities who have made it not only acceptable but cool to take an active interest in clothes, like Lil Nas X, Harry Styles, Kanye West, A$AP Rocky and Timothée Chalamet. And now when young people create fashion content online—such as posting reels on TikTok and Instagram, or chatting in Discord channels—they do so with their faces unobscured. Breaking from Brummell’s concept of the dandy’s pose, many have reframed style as a skill that can be taught and learned, not as an expression of some unfathomable, superior inner character.

In the fabric of mainstream culture, the threads of male apprehension about style are still tightly woven, a reality I confront regularly on X. Yet it’s undeniable that a new narrative is emerging. We may never find an answer for what it means to be—and to dress—masculine, but the taboos and gender norms that previously kept men from developing an interest in fashion exert less of a distorting influence than they once did. One can imagine that if Tom Wolfe wrote “The Secret Vice” today and suggested that men are afraid of reading clothing catalogs in public, he would be openly mocked on X with memes like “Fellas, is it gay to buy a jacket?” And perhaps now a man in search of a suit to impress a female friend at a wedding won’t feel the need to sign up for an anonymous style forum to figure out how to dress—he can ask for advice openly.

Art credit: Christian HeikoopNormcore, 2015. Courtesy of the artist. 

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