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The 9 best-dressed businessmen of all time

These entrepreneurs and CEOs know how to dress the business

Gerry McGovern - Chief Design Officer at Land Rover

Whilst the label businessman may evoke images of characterless city suits with dark socks, muted ties and too low trouser hems, a small handful however, have soared high in the realms of gentlemanly style (a quality which no doubt mirrors the businesses these men have lead, too).

The unavoidable truth is that success in the boardroom is matched with adroit sartorial skills – because what man in their right mind will take you seriously if your choice of clothing doesn’t punch as hard as your business plan?

And so, gentlemen, these are the businessmen we believe are worth taking both entrepreneurial and wardrobe advice from…

Gianni Agnelli

The 9 best-dressed businessmen of all time
Fiat magnate and style icon, Gianni Agnelli

Gianni Agnelli or L’Avvocato (‘The Lawyer’), as he was nicknamed, was an esteemed Italian industrialist, society playboy and, at the height of his powers, the richest man in Italy. He was however, known as much for his idiosyncratic approach to style as his unrivalled business prowess.

From embodying the ideals of sprezzatura – artful dishevelment – with sharp suits contrasted with skewed ties to the quirks such as a propensity for wearing his watch on the outside of his cuff; he reportedly didn’t have time to adjust his sleeve to check the time. Agnelli has always been a source of inspiration when it comes to both business and rakish styling.

Ralph Lauren

Ralph Lauren shot by Alexi Lubomirski for Harper's Bazaar

The billionaire started his eponymous empire with humble beginnings – selling ties to small New York shops – and the rest, as idiom dictates, is history. The man who has brought preppy style to the masses represents his brands’ mantra better than anyone.

Outside of clothes, he’s become increasingly known for his insane car collection that is easily one of the best in the world, proving himself a real man of style.

Lapo Elkann

Lapo Elkann by Fulvio Maiani for Forbes

The grandson of Gianni Agnelli, Elkann has inherited more than just a position in the company and the bank balance, but his grandfather’s way with the wardrobe also. A modern street style superstar, known for his bold suits, big lapels and distinctive glasses, Elkann established design and lifestyle company Italia Independent in 2007 to market his creativity and style.

Paul Newman

The 9 best-dressed businessmen of all time

Paul Newman is up there with Steve McQueen when it comes to cool (yes, two style icons that will forever rival for first place). Not only did Newman cultivate a killer career as a movie star, but he also took a turn as a professional racing driver – finishing second in Le Mans no less, donating hundreds of millions of dollars to charity and possessing icon worthy sartorial skills.

Newman, with writer, A. E. Hotchner, founded Newman’s Own, a line of food products, in 1982 and the company as policy, donates 100% of the after-tax profits from the sale of its products to charity.

Luca Cordero di Montezemolo

The 9 best-dressed businessmen of all time
The man who saved Ferrari, Luca Cordero di Montezemolo

The man who saved Ferrari, Agnelli appointed Montezemolo as president of the Prancing Horse in 1991, the marque had been struggling since founder Enzo Ferrari’s death. Montezemolo turned fortunes around and carved out a long successful career in motorsport, forging a formidable reputation in business in the process.

Unlike Agnelli and Elkann, Montezemolo’s style is rooted in the traditional – forming a seriously sharp wardrobe from timeless essentials and attention to detail. His flowing, majestic mane helped his cause, too.

David Lauren

The 9 best-dressed businessmen of all time
Ralph Lauren's youngest son is a success in his own right

The youngest son of aforementioned Ralph, David Lauren has taken more than a few pages of his father’s sartorial playbook over the years. Classic Americana and sharp suits run through his signature style.

Currently Executive Vice President, Global Advertising, Marketing and Communications at Ralph Lauren Corporation, David has been key in establishing the company digitally since the turn of the millennia.

Aristotle Onassis

The 9 best-dressed businessmen of all time

Known to his friends as Ari, Onassis amassed the world’s largest privately owned shipping fleet and was one of the world’s richest and most famous men of his time – thanks to personal and professional success.

Despite carrying a larger frame, Onassis called on the talents of a great tailor – Caraceni of Milan – for an impeccable fit to his suits cut from world class fabrics. His penchant for double breasted suits is well noted and he remains one of the best wearers of the divisive garment.

Gerry McGovern

Gerry McGovern - Design Director at Land Rover

Land Rover’s Chief Design Officer Gerry McGovern has not only steered the British car brand into record-breaking success (with a record year for Jaguar Land Rover which saw sales up by 24% recently confirmed upon the announcement of the Range Rover Velar), but he also quite simply never puts a foot wrong with his style credibility.

What’s more, he’s also a professor at the Royal College of Art, where he once specialised in automotive design in his student years. And today, he’s arguably the best-dressed car designer out there, gents.

Christopher Bailey

The 9 best-dressed businessmen of all time
Burberry's chief creative and soon to be president, Chris Bailey

Up until recently, Bailey was CEO as well as chief creative at Burberry, running everything from collections to marketing decisions and architecture. The fashion designer by trade has led Burberry into the digital era and will transition to the role of company president (as well as chief creative) in 2017.

Bailey relies and pulls of with aplomb, a sleek, stripped back wardrobe. Slim cut suits and a plain shirt – no tie – have become his go-to uniform. Unyieldingly classic and consistently sharp, Bailey’s found his uniform and stuck to it, an applaudable feat in the fickle world of fashion.

Further Reading