Sadness as an aesthetic has always been much easier conveyed with women’s fashion. From Victorian mourning garb to 80s goths, sadness in womenswear has carried a strain of flamboyance rarely permitted in men’s clothing. Women, for example, can signal their grief with Lana Del Rey-style ostrich feathers the colour of an oil-slick, or a cascade of jet beads, or a netted veil. Men, on the other hand, must make-do with a suit – one that will inevitably be reused for the office or a wedding. But it wasn’t always, and doesn’t have to be, the case. Throughout history, many men have claimed sadness as their signature style, rejecting the idea that men shouldn’t feel, and inspired countless others to do the same. Here are ten of history’s most fashionable sad boys, from Lord Byron to Yung Lean.

YOUNG WERTHER

The OG sad boy style icon didn’t actually exist. In 1774, German author Johann Wolfgang von Goethe wrote a novel called The Sorrows of Young Werther, about an artist tormented by quarter-life angst and his unrequited love for a woman named Charlotte. Werther was the Regina George of Sturm und Drang Germany: he had a fetish for yellow waistcoats and blue frock coats, and soon after publication, every fashionable young man in Europe was wearing yellow waistcoats and blue frock coats. Some wanted so badly to emulate Werther they even aped his suicide method (by pistol, and with a copy of the book in their pockets), thereby dubbing the phenomenon of copycat suicides “the Werther effect.”

LORD BYRON

The greatest trick John Milton ever pulled was convincing the world Satan was a sexy anti-hero. But Lord Byron one-upped him by actually becoming this archetype, to the point that it’s named after him. Eminently fuckable, the Byronic hero is a miserable, cynical, anti-social asshole with a cocktail of neuroses who nevertheless seduces countless men and women. And Byron made no distinctions between the Byronic hero on and off the page, earning the title “mad, bad, and dangerous to know” from one of his lovers. One biographer described his aesthetic as "dressed in black, hellishly pale and poetic, a metropolitan Hamlet who specialised, he soon gave notice, in country matters.” Byron was such a style icon that his legacy lies not in clothing, but in a pose: his infamous “underlook” has been adopted by everyone from James Dean to Marlon Brando to every Kubrick character ever.

FRÉDÉRIC CHOPIN

Another celebrity of the Romantic era, Chopin was famous for his melancholy and poetic treatment of the piano. He was also famous for dying, fashionably, of tuberculosis. Although the 19th century mostly preferred the “consumptive chic” look for women, Chopin made TB a sex symbol. “Chopin coughs with infinite grace,” gushed his lover George Sand to a girlfriend while he spit up blood, and towards his death a friend snarked, “all the grand Parisian ladies considered it de rigueur to faint in his room.” Even without his illness, Chopin’s persona was very in vogue. Like Byron, he knew damn well he was a gloomy fuccboi, once describing himself as a poisonous mushroom while Sand likened their relationship to dying by pinprick. He also took dandyism to hardcore extremes, demanding a new pair of kid gloves every day.

CHARLES BAUDELAIRE

The definition of enfant terrible, Baudelaire was the Keith Richards of 19th-century French poetry. His drug-fueled benders, misanthropy, and obsession with lesbianism may seem very MFA-dudebro today, but back then he was a despondently hedonistic rock star who put even Byron to shame. “I can barely conceive of a type of beauty in which there is no melancholy,” he wrote. He became arguably the most influential French poet ever with The Flowers of Evil, his decadent treatise of sex, death, and ennui. He was a provocateur in fashion as well: his huge amounts of debt, which his mother had to pay after his death, were mostly for clothes. Baudelaire also sneered at other dandies, preferring all-black to their foppish glamour and declaring dandyism not just a fashion statement, but a form of spirituality. Catchphrase: “To live and die before a mirror.”

PETER MURPHY 

The Godfather of Goth, Peter Murphy’s likeness inspired not one, but two other goth icons: the guilt-ridden, suicidal Dream of Neil Gaiman’s The Sandman and the tortured, self-harming super-anti-hero of The Crow. He himself has rejected the gloom-and-doom stereotype cast upon his music, despite the lachrymose lyrics and despairing vocals, stating in one interview that depression was a very small part of his life. But as much as he may resent it, grudgingly giving birth to an entire subculture dedicated to aestheticising melancholy has secured his pop cultural legacy as a sad boy. And although he has distanced himself from the goth subculture and denies his looks as “fashion,” no-one can ignore his style influence on both babybats and haute goths like Rick Owens, Alexander Wang, and Gareth Pugh.

MORRISSEY 

Everyone’s favourite “sad bastard,” Morrissey has been milking the whole mimetically nihilistic thing since 1982. Although his lyrics might indicate otherwise, Morrissey’s fashion is far from the sleek leather, sharp black suits, and softcore bondage gear favored by old-school goths who warble about the same subjects. His sad boy fashion, at its heyday, was a very soft, minimalist version of the New Romantics uniform: a clavicle-baring silky blouse sliding off the shoulders or shapeless knits over baggy pants, plus a James Dean-meets-Eraserhead bouffant.  

SETH COHEN 

Another fictional character, The O.C.’s Seth Cohen was proof that sad boys could express their woe in things besides poet shirts and black cloaks. This neurotic, fast-talking, Death Cab-addicted dork was responsible for the sexual awakenings of many a young misfit in the 2000s, even if today he would undoubtedly be the sort to list “sapiosexual” on his Tinder bio. He’s been described as “emo-lite” and a denizen of the liminal space between “hipster” and “emo,” but style-wise, he was more nerdy and preppy than anything. Honestly, at times even his dad looked more emo than him. You can thank him for the argyle-skinny jeans-converse pandemic of your college years.

GERARD WAY

Although his pet name for emo was “fucking garbage,” My Chemical Romance’s ex-frontman was the mascot for eyeliner-besmirched adolescent angst. Howling vampire metaphors over Mad Max guitar riffs as a way to cope with issues of depression and substance abuse, he provided many of our middle school years with a much-needed catharsis. Way’s sad boy aesthetic went through several phases: shag haircuts and a Johnny Depp-esque affinity for layering, vampire schoolboy chic, peroxide anime military commander, and high-octane post-apocalyptic road racer. His most emulated look, however, has been his skeleton onesie.

DRAKE

Aubrey Graham’s status as a style icon has been the topic of fierce deliberation and spawned countless thinkpieces, but there are two things that are indisputable: 1) He is a sad boy, with sad lyrics in sad songs, immortalised in sad memes. 2) His style is certainly striking, for better or worse. Drake’s clothing brand OVO – a hybrid of Supreme and Jersey Shore souvenir garb – is not worth dwelling on here, but he deserves some credit both for his warm embrace of normcore at its conception and for providing Pinterest fodder for an entire generation of Chicago art hoes.

YUNG LEAN

Bucket-hat apostle, post-internet aesthetic executioner, kerning abuser. Three years ago, the Swedish teen unleashed a new age of sad boy-dom with his aptly named musical collective and unwittingly started a movement. I hold him personally responsible for not only allowing vaporwave to leak IRL, but for encouraging its unholy coupling with streetwear. You know the staples, even if you think you don’t: frowny faces, Japanese and Arabic as accessories, sportswear brands, Arizona iced tea, and the uncanny ability to simultaneously communicate in and be a meme. Delve too deep into Yung Lean’s aesthetic and it develops a slight air of the sinister – from certain angles, it comes across as an AI simulating teenage ennui. Although his look has calmed down somewhat, his reign as this era’s Prince of sadness remains unchallenged.