Happy nearly new decade – and welcome to this unusual edition of MR PORTER’s On The Town column. Why unusual? Well, because we’re looking at a whole decade, the customary “Who wore it best?” question doesn’t quite fit. What fits better is something more like “Who wore it most?” By that, we mean this: as with cars, hairstyles, architecture and art, clothes come with an inbuilt time-stamp, which becomes even more apparent as the years pass. So, say, the first time the world saw Mr James Dean in Rebel Without A Cause, The Beatles on the cover of Sgt Pepper’s Lonely Hearts Club Band, Mr David Frost interviewing President Richard Nixon, or Mr Eddie Murphy in Delirious, they all appeared utterly modern, contemporaneous and cool. But just look at those looks now. They scream 1955, 1967, 1977 and 1983 respectively because they were among the most archetypally defining outfits worn by the most archetypally defining men of their time. So, who will history remember as the most-defining men (and looks) of the decade we’re about to depart? Here are our best guesses.

Avatar was on general release. Mr David Cameron seemed like a good idea. Fauxhawks were still a thing, for goodness’ sake. Seen through the rear-view mirror of today, 2010 suddenly seems a very distant dot. One of the most powerful contrasts between then and now is illustrated by our nominated best-dressed commander-in-chief for 2010, President Barack Obama. His 2009 inauguration as the first African-American president in US history was seismic, and by 2010, he was exhibiting total mastery of the role. Not least impressive was his deft deployment of unfussy precision-cut Italian suiting – he is a big Canali fan – in a silhouette almost as harmoniously balanced as the world then seemed to be. Happy days.

It was the broodingly meaningful silence of Mr Ryan Gosling in Drive – not to mention his finely put together satin-jacketed style – that made 2011 this Mickey Mouse Club alum’s breakout year as an international masculine cipher. Part of the reason for his ubiquity that year was a rare ability to dress louchely down (a piped silk pyjama shirt at a Cannes Film Festival photocall) just as convincingly as he adorned himself in more conventional (though, actually, not all that conventional) movie-star tailoring – the blue tuxedo above being a standout. He also caught the mood of a moment. So potent was his allure, in fact, that when Mr Bradley Cooper was that year named “sexiest man alive”, Mr Gosling’s fans – a few of them, at least – took to the streets in protest.

Sure, he wore a muzzle and sounded like Sir Ian McKellen with a throat infection as Bane in that (arguably) best-ever Batman flick, The Dark Knight Rises. But 2012 was also notable for Mr Tom Hardy as he grew into character as a bit of rough who could look extremely smooth, as exemplified here. This contradiction nicely prefigured a sartorial schism that would soon boil over. For 2012 was perhaps the peak moment of what I fondly remember as “the pocket-square years”, a period of unironic dandyism (itself arguably a reaction to sub-prime), exemplified by the double-monk-strapped peacocks of Pitti and popularised in no small part thanks to a fledgling online menswear retailer called… MR PORTER.

All hail Mr Kanye West, the single most influential man in early 21st-century menswear. His unswerving conviction that he is the greatest musical artist in the world might be a little de trop, but the impact of his collaborations with Louis Vuitton, then Nike, then adidas – plus the fact that he was the agent that first brought Mr Virgil Abloh to Paris – cannot be overestimated. This was the year in which Mr West put the calamity of his 2012 Paris runway debut behind him (never forget) and found his destiny – and perfect spousal complement to his fashion powers – in Ms Kim Kardashian. In what would prove to be Mr West’s decade, this was his year. And given that so much of what Mr West says is going to happen actually happens, it’s perfectly feasible that whoever collates this list for the 2020s might be doing it in the era of President West…

There was a lot going on in 2014, but nothing was going on much as Mr Pharrell Williams’ headlining headwear. Beginning at the Grammys in January, and then ricocheting back and forth down the year, Mr Williams’ titanic titfers were the key accessory of the year. Interestingly, this hat was, in fact, ancient – an archive piece from Ms Vivienne Westwood and Mr Malcolm McLaren’s very first runway show in 1983. Like Excalibur, though, it was clearly a magic item that had long been waiting for a man worthy of it to unleash it upon the world. Mr Williams’ hat not only provided us with one of the earliest fashion memes, but also suggested – as all supersized clothing trends do – the pendulum of fashion was about to swing in a new direction.

Unlike most Hollywood movie stars Mr Shia LaBeouf (very) apparently does not retain a stylist. But if in fact he does, well, this stylist is a genius. For Mr LaBeouf is a paragon of got-dressed-in-the-dark spontaneity that produces car-crash clothing combinations, which, in 2015, just so happened to foreshadow the shifting hive mind of masculine taste with uncanny accuracy. His pink leggings aside (Google these, please), this is Mr LaBeouf’s ne plus ultra ensemble of the decade because it effortlessly presages the lurch to normcore/gorpcore/dadcore that would soon grip the wider world. If Mr Demna Gvasalia was the god of this particular trend (and he was), then Mr LaBeouf was its Cassandra.

The second half of the 2010s belonged to Gucci, after Mr Alessandro Michele took the helm of the house in 2015. And no man has epitomised the chin-rubbing, post-modern maximalism of the Italian house under his stewardship more than Mr Jared Leto. You could argue that Mr Michele’s particular vision of masculinity is to Mr Leto what a musclebound killing machine was to Mr Arnold Schwarzenegger: that is, the role he was born to play. Mr Leto has reprised his Gucciness over and over again in a myriad of Mr Michele’s episodically extravagant full-look flourishes (also, that green coat meme), but none was quite as Mr-Leto-in-Gucci as this Mr-Leto-in-Gucci. It is a look that will resound down the ages as being precisely of its time.

Ah, streetwear. The luxurification of sportswear into a full-scale fashion category began with Lanvin in the mid-2000s, but reached its peak with 2017’s Mr Kim Jones-overseen collaboration between Louis Vuitton and Supreme. This was the moment when two undisputed masters of enforced scarcity merged their aesthetics and demographics, and the world went crazy. Although pretty much anyone who’s anyone posted some LV x Supreme merch that year – it was a badge of cultural relevance – it fell to Mr Justin Bieber to act as the perfect embodiment of a youth-driven fashion uprising that has since prompted many traditional purveyors of “luxury” to change everything about the way they do business.

A$AP Rocky is a promiscuous inhabitant of the fashion world, with a knack not only for following it, but leading it, too. Although invested in the production of clothing himself, he remixes his own public image with a free-flowing disregard for label or genre and clashes tailoring against sportswear with iconoclastic glee. Though it’s hard to single out one particular high point in his recent sartorial journey, 2018 was a doozy thanks to his personal endorsement of a runway trend – the granny look – which rapidly colonised the internet, and even the streets. A$AP Rocky reputedly first adopted his babushka-style headscarf for practical purposes – apparently, he had acquired a livid scratch on his face that he wished to obscure from the waiting paparazzi. To be able to create a worldwide trend – and then parlay it into musical material – on the basis of a scooter accident after a badly landed “pop-up wheelie” is the sign of a bona fide style titan.

For this final defining man slot, it is highly tempting to include one Mr Timothée Chalamet, who, thanks to the tutelage of Mr Haider Ackermann and his own natural fashion curiosity, has emerged as a protean menswear superstar. But the transition of one decade to another is a time to reflect not just on what has changed, but also what remains certain. And in menswear, nothing has remained as unswervingly sure for so long as the enduring coolness of Mr Brad Pitt. After a relatively quiet few years, this century’s Mr Steve McQueen returned in 2019 to the cultural fore thanks to the release of Once Upon A Time In Hollywood and looked perfectly himself (both neutral and impactful) at the Mexican premiere of Mr Quentin Tarantino’s excellent movie. Mr Pitt is the iPhone of men: very well put together in the first place, but apparently also subject to never-ending upgrades.

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