Fashions come and go, but style persists – these have been some of our favourite well-dressed men over the years.

During the five years since MR PORTER launched, we’ve put together a long list of style icons. To achieve this, we’ve comprehensively discussed and recorded who’s worn what, how they wore it and whether it worked. For The Journal, we’ve distilled that list down to an essential 10 men whose individual approaches to dressing give them permanent relevance. Their sartorial reputations have less to do with their clothes and more to do with their very being. Fashion normally works by offering men garments that make them look hip, but these icons run things in the opposite direction. They made the clothes cool. In their different ways, they embody the sentiment first expressed by the Greek Stoic philosopher Epictetus (55–135AD), who wrote, “Know first who you are, and then adorn yourself accordingly.”

Now that the late French designer’s brand is under the direction of Mr Hedi Slimane, and going from strength to strength in a quite different guise, it’s easier to judge Mr Yves Saint Laurent’s enviable personal style. It’s also intriguing, given that our era is dominated by Italian influences, to look back to a time when France was the last word in relaxed elegance. The enduring influence of Mr Saint Laurent, who died in 2008, is such that his rumpled cotton double-breasted suit, with its patch hip pockets and wide lapels, would wow the street-style photographers at the Pitti Uomo fashion fair this summer, and any summer.

What does it say about the peerless elegance of the 1930s that baseball player Mr Leroy “Satchel” Paige looks more like a hip jazz musician than an athlete? The spear-point collar on his shirt and the loosely cut sleeves on the suit might mark Mr Paige out as a follower of fashion, but the appeal of his clothes has endured even longer than his 40-year career as a pitcher. He was famously cocky and charismatic – qualities that his outfit seems eloquently to project. A man’s clothes should tell his story, and be relatively honest about it.

Given their visual acumen, it’s unsurprising that many painters are snappy dressers. Mr Lucien Freud, one of the greatest British artists of the past 60 years, was no exception. In later years, he wore a grey scarf so frequently it become something of a trademark, and he’s also said to have had a penchant for extraordinarily expensive leather jackets from French luxury brand Zilli. This shot from the 1950s speaks more directly to modern tastes, not least because of the way photographer Mr Cecil Beaton faithfully recorded the peeling paint on the wall in the background. Mr Freud’s slim sweater and the sporty stripe on his trousers lend his outfit a contemporary air. While his style is worth emulating, his intensity is surely unattainable.

The idea that a chat show host could offer sartorial inspiration seems outlandish in 2016, but US television legend Mr Johnny Carson knew how to dress, and showed this over the 30 years he anchored The Tonight Show. Nearly half a century after he made a habit of wearing odd jackets with dark trousers, it once again looks very relevant. Here, Mr Carson is sporting a natty double-breasted blazer (one of the most versatile garments you can own, by the way) and slacks, which lend him an air of authority yet approachability. We’re awarding him extra style points for his monochrome colour palette and the sliver of white shirt cuff poking out from his jacket sleeves. A masterclass in contemporary elegance.

The late French singer was a man who seemed to personify the notion of roguish Gallic charm. His good living – he smoked, drank and behaved with reckless abandon – was legendary, and his sense of style correspondingly louche. He set a fine example for men who want to make tailoring their own, as he demonstrates here in a three-piece pinstripe suit worn without a tie or socks, but with his favourite white Repetto dancing shoes.

One of the foremost fashion photographers of the second half of the 20th century, Mr Richard Avedon, a New Yorker, enjoyed prodigious success under the mentorship of legendary art director Mr Alexey Brodovitch. As an expert in the image business, Mr Avedon knew that simplicity in dress was often the best option, particularly on formal occasions.

It’s testament to Lord Byron’s 19th-century Romantic poetry that, despite his extraordinary life, he is best known for his literary talents. Although described in 1812 by Lady Caroline Lamb as “mad, bad, and dangerous to know”, we retain a guilty admiration for his romantic exploits, as well as for the claret shade of his velvet robes.

The much mourned sartorial chameleon Mr David Bowie could easily be five different style icons, but, to our eyes, his best-dressed era was the late 1970s and early 1980s, when he mined a seam of fashionable tailoring that proves it’s possible to wear the traditional elements of menswear but make them entirely your own. While few men could carry off his more outlandish looks – Ziggy Stardust leotard, anyone? – this school tie, tweed blazer and overcoat combination provides a lesson in style from which we can all benefit.

His Imperial Majesty Haile Selassie was the emperor of Ethiopia from 1930 to 1974. His full title was His Imperial Majesty Haile Selassie I, King of Kings, Lord of Lords, Conquering Lion of the Tribe of Judah, and Elect of God. He was also, at the time of his reign, the most be-medalled ruler in the world. As befitted someone who could trace his ancestry back to King Solomon and the Queen of Sheba, he could certainly rock a regal look or two.

Mr Colin Tennant, Third Baron Glenconner, was famous for having fun. And who can criticise a guy for that? In 1958, he bought the West Indian island of Mustique – most of us make do with just booking a hotel – and transformed it into a multi-millionaire’s playground in the late 1960s. A gregarious host, and close friend of Princess Margaret, Lord Glenconner dressed like the quintessential tropical patriarch, peppering his wardrobe with bright colours, tunics and wide-brimmed hats. And somehow it worked.