These are the most stylish Scotsmen in history

From fashion designers to racing car drivers, these are the men who set the pace when it comes to Scottish style…

Over the years, Scotland has produced some particularly impressive individuals. From John Logie Baird to Alexander Graham Bell, we owe the country everything from our televisions to our telephones. But what about our wardrobes? The inventors and innovators of Scotland may still influence our daily lives, but what about its style icons?

We’re certainly impressed and influenced by the styles of more modern Scotsmen. Whether it’s Richard Madden or Sam Heughan, the country’s latest generation of trend-setters are advocating everything from tartan trousers to the classic kilt. Below, we’ve rounded up six Scots who came before this new wave — men from fashion designers to racing car drivers who helped set the pace when it came to Highland style… 

Sean Connery, Actor

Well, where else would we start? After being cast as the first official cinematic James Bond, Connery soon became a style icon. From his character’s grey Goldfinger three-piece (tailored by Anthony Sinclair) to his personal penchant for tartan or tweed sports jackets, the Edinburgh-born actor wasn’t only renowned for his wardrobe in Scotland — but is widely regarded to be one of the best-dressed men of the entire 20th century.

Our enduring memory of the late actor, and perhaps his finest menswear moment, was when he buttoned up a dinner suit for the first time in Dr No. Cut from midnight blue satin and with a silk shawl collar, it’s a milestone in modern male dressing — and an image men around the world still refer to at every black tie opportunity. But even Connery’s off-duty dressing (lightweight linen shirts, turtleneck jumpers, golfing attire) holds valuable style lessons. 

Jackie Stewart, Racing Driver

There have been moments when Sir Jackie Stewart’s style has veered dangerously off-course (the tartan flat cap is not an accessory most men should be trying on for size). And yet, in his younger, petrol-powered days, the Dunbarton-born racing driver knew how to throw together an ensemble almost as well as he could throw his Tyrrell 003 around a Formula One track. 

The flat cap has always been a mainstay of his look, but it didn’t develop its tartan pattern until somewhere around the turn of the century. Before then, Stewart would pair a pared-back cap with thick-rimmed, chunky aviator-style sunglasses whether he was trackside or enjoying a day off. But his best menswear manoeuvre? A simple suit; shifted into a higher gear with pitch-perfect use of accessories from wristwatches (his first was a yellow-gold Rolex Day-Date) to bold neckties.

David McCallum, Actor

Born in Glasgow, Scottish actor David McCallum is perhaps best know for his work in super-stylish television series The Man from U.N.C.L.E. And it was during this 1960s stint on the show — in which he played suave Russian secret agent Illya Kuryakin — that McCallum exported his Scottish style to the bustling backlots of Hollywood. 

Back then, the British style of suit was more structured than baggier American cuts, and McCallum’s neat lapels and tailored trousers stood him apart from the contemporary American crowd. But it wasn’t just his suits. The actor, often pictured with his then-wife Jill Ireland during the 1960s, also knew how to knock an off-duty outfit together. Whether it was chunky knitwear, casual shirts or even just a simple, plain white T-shirt, he always understood the assignment (top secret or not…).

John Boyd, Milliner

When Scottish milliner John Boyd died in 2018, the world lost a fashion icon. Born in Edinburgh in 1925, Boyd trained in London with the Danish royal hatmaker Aage Thaarup — and went on to design hats professionally for over 75 years. During his career, Boyd created accessories for British royals including Diana, Princess of Wales, Anne, Princess Royal and, more recently, Catherine, Duchess of Cambridge.

But, behind the scenes, he was also something of a snappy dresser. Though his own outfits may have lacked the bombast and interest of his more noteworthy hats, Boyd’s suits often added quirky, idiosyncratic details that laid bare an exceedingly creative mind. From statement shirts and single-button suit cuffs to tartan trousers and off-centre ties (note the double use of his tie as a pin-cushion above), Boyd’s flair for fashion extended way beyond his day job.

Tommy Armour, Golfer

Nicknamed ‘The Silver Scot’, Tommy Armour was born in Edinburgh and went on to have an illustrious golfing career (winning the 1927 U.S. Open, the 1930 PGA, and the 1931 Open Championship). He also coined the term ‘the yips’; referring to a sudden and unexplained loss of skill by a professional athlete. But ‘the yips’ wasn’t Armour’s only contribution to popular culture — he also brought golfing style firmly into mainstream menswear.

It’s a style that has also seen a recent resurgence, but Armour’s initial championing of classic golf attire saw him inspire men both on and off the fairway to pull on their plus fours, doff Baker Boy caps and seek out every piece of patterned knitwear from a V-neck jumper to a sweater vest. Especially noteworthy were Armour’s neckties; whether double-sided and silken or loudly-patterned and practically-pinned, he wouldn’t take to the green without one.

Ronald Paterson, Fashion Designer

And, finally, Ronald Paterson. It’s another name you’ve likely never come across — but you’ve certainly seen his work. Paterson, like John Boyd above, left Scotland early in his life for the style scene of London. By 1947, he had opened his own couture house, and amassed many important, even noble clients. He was even awarded a fashion award from The Sunday Times in 1966.

But his most impressive work was captured on film. Despite being something of a conservative dresser, Paterson acknowledged detail and precision like no-one else. In fact, it’s his almost slavish adherence to suiting rules (not to mention a fun and far-reaching tie collection) that squeezes him onto this list. And that deep knowledge of menswear tradition is what made him the perfect consultant for costume departments. Among the films that called on his suiting expertise? Roger Moore’s 1977 critically-praised The Spy Who Loved Me.

Want more style icons? Here are the best-dressed men of the 20th century…

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