Top Male Fashion Icons

From the Italian Renaissance to the streets of Atlanta, we’ve compiled our picks for eight icons who have redefined elegance through the ages and made menswear what it is today.

1. Baldassare Castiglione

If we had a dollar for every time we heard the term sprezzatura being misused, we’d be able to purchase for ourselves a palm-sized Renaissance courtier, replete with silk breeches and a brocaded robe, to give us advice as we dressed in the morning. Castiglione, the humanist thinker who started it all, is a monumental figure in fashion history for having established that single, eternal, universal principle of menswear: elegance is not an aesthetic, but an attitude. We have him and his eloquent arguments about the importance of studied carelessness – aka sprezzatura – to thank for iteration after iteration of graceful, effortless Pitti peacocks. So the next time you see a man wearing his watch over his cuff, or his tie with the skinny end peeking out, know that he probably took inspiration from the words of this Italian genius.

2. Oscar Wilde

An unwavering commitment to witty and eloquent prose is something few writers dare dream of, let alone achieve. Oscar Wilde did just then, and then matched it with an equal level of extravagance in his dressing. Flâneur of the highest order, the Victorian writer was precisely the sort of urbane, sophisticated aesthete Baudelaire wrote about in Les Fleurs du Mal: he reportedly walked around London in a billowing fur coat and cravat, gaily tapping his way along the streets of Mayfair with his gold-headed ivory cane and soaking in the city’s richest splendors. His unblushing subversiveness in conduct and dress led, of course, to his eventual downfall, and we truly do regret being unable to say a little party never killed nobody… but man, he sure wore the hell out of that great blooming lapel buttonhole.

3. Duke of Windsor

If Oscar Wilde was an exercise in luxurious ornamentation, then the erstwhile King Edward VIII was an exercise in luxurious understatement. Known as much for his scandalizing abdication of the British throne as for his immaculate wardrobe, the Duke of Windsor married an American divorcée socialite, left his country, and became a pioneering vision of post-monarchical sartorial splendor, one double-breasted suit at a time. Perhaps most importantly, he introduced to the world the crafty maverick that was Frederick Scholte – a Dutch-born tailor we now know as the inventor of the Savile Row drape cut. With its soft, generous chest and waspish waist, each jacket gave a majestically masculine stature to an otherwise physically unimpressive man: a man who, nevertheless, wore every last suit with appropriate devil-may-care aplomb. Besides, what could be more stylish than lounging about in the Caribbean as Governor of the Bahamas, wearing a lightweight wool suit and a smoking pipe in hand.

4. John F. Kennedy

From British monarchy to American aristocracy: throughout the second half of the 20th century the Kennedys were without a doubt the United States’ royal family, both in the political and style departments. Before JFK, the Ivy prep aesthetic was just a conservative wardrobe worn by a wealthy but tiny subculture of the American East Coast. In his less than three years in the White House, however, Kennedy managed to propel seersucker suits, repp ties, and madras trousers into the international spotlight, prompting generations of men to ditch their fine Italian tailoring in favour of more casual stateside styles. Whether navigating the Cuban Missile Crisis in a Brooks Brothers jacket or yachting off of Nantucket Bay in a J. Press Shetland sweater, the 35th president of the United States of America never once looked anything but at home.

5. Marcello Mastroianni

As stylistically groundbreaking as it was, Italian neorealist cinema will always remain memorable to us for one thing alone – the sheer magic of maestro Mastroianni roaming Italy in his suit. Which, by the way, invariably remained the simplest of ensembles: black or charcoal single-breasted suit, white poplin shirt, and slim black tie, like the continental predecessor of London’s mod mobs (with none of the uncouth brashness). Slinking about on the silver screens, the breathtakingly cool Roman showed the world what Italian style, stripped of its stereotypical extravagance, really meant – a Mediterranean nonchalance, equally unflappable as an impoverished Sicilian aristocrat plotting the end of his loveless marriage in Divorzio all’italiana, as a listless journalist amidst bourgeois Roman debauchery in La Dolce Vita. More than anything else, of course, he taught us that the best accessory to complement any outfit is an abundantly buxom Italian bombshell – preferably one named Sophia Loren.

6. Hamish Bowles

We’ll say it right off the bat: no man in history has swanned forth with such a bold sense of personal style as one Mr. Bowles. Contemporary dandy par excellence, the European editor-at-large of Vogue has been pushing the boundaries of menswear for decades, drawing on his private collection of haute couture – one of the largest in the world, stored in various undisclosed warehouses across America – for inspiration. He blurs the boundaries between menswear and womenswear in the genteel manner only an upper-middle class Englishman can: never one to fall pretty to understatement, he takes the classic tailoring format and festoons it with macro-checks, boating stripes, and everything in between. With such unwavering panache and infectious sartorial festiveness, the proof is in the Hamish pudding that a gentleman’s best friend is his confidence. No wonder, then, that he is the still most powerful man in fashion.

7. André 3000

In the hip hop industry there are two major artistic periods: pre-Outkast and post-Outkast. Whereas rappers previously only had socially acceptable access to the hyper-ostentatious conspicuous consumption of bling bling, oversized monograms, and oversized bling bling-ed monograms, André 3000 stepped forth from the mean streets of Atlanta with a revolutionary proposition: that one could don an ivory shawl collared dinner jacket and still be a well-respected, Grammy Award-winning hip hop giant. And while his style is as entertainingly eclectic as his music, few other artists have been able to translate their aesthetic vision from one medium to another with the playful touch that he somehow possesses. It might be difficult to wrap our heads around this now, but the ripples created by his fearless fashion experimentation has paved the way in the rap landscape for such hip hop sartorial superstars as Pharrell, Tinie Tempah, and – bizarre Twitter feuds or not – Kanye West.

8. Alan See

If showing up to a black tie dinner in monochrome traditional Chinese silk robes doesn’t immediately grant you the status of style icon, then we don’t know what else will. The Malaysian-born, Hong Kong-based impresario behind the wildly successful haberdasher The Armoury bespeaks something of a maverick streak in his sartorial imagination, that makes him a refreshingly original counterpoint to all the other dandies out there. Underlying all of this, surely, is a remarkably keen eye and profound understanding of how patterns and colours work together, particularly against the Asian complexion and silhouette. His alchemy of sober tones and lively prints ensures he is a latter-day Fellini. Cutting a striking figure as the image of contemporary Asian elegance, See’s singular aesthetic vision has redefined – for all of us – what it means to be a stylish man in the 21st century.

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Published April 9, 2016
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