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The most stylish businessmen of all time


These entrepreneurs and CEOs know how to dress the business

The most stylish businessmen of all time
Ralph Lauren's youngest son is a success in his own right Jeremy Liebman
The Gentleman

Whilst the label businessman may evoke images of characterless city suits with dark socks, muted ties and too low trouser hems. Yet for a small handful, success in the boardroom is matched with adroit sartorial skills, these are the businessmen who worth taking both entrepreneurial and wardrobe advice from.

Gianni Agnelli

The most stylish businessmen of all time
Fiat magnate and style icon, Gianni Agnelli Photo by Getty

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

The most stylish businessmen of all time
Ralph Lauren stepped down as CEO of his company late last year Photo by Indigital

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

The most stylish businessmen of all time
Gianni Agnelli's grandson and businessman Lapo Elkann Photo by Margherita Chiarva

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 most stylish businessmen of all time
Paul Newman during a trip to Venice, 1963 Photo by Cameraphoto

Paul Newman is up there with Steve McQueen when it comes to cool. Not only did he 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 was also a successful entrepreneur.

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 most stylish businessmen of all time
The man who saved Ferrari, Luca Cordero di Montezemolo Photo by Carofei Imago Economica

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 traditional, forming a seriously sharp wardrobe from timeless basics and attention to detail – the flowing, majestic mane helped his cause also.

David Lauren

The most stylish businessmen of all time
Ralph Lauren's youngest son is a success in his own right Photo by Jeremy Liebman

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 running 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 most stylish businessmen of all time
Greek shipping magnate and noted playboy, Ari Mr Aristotle Onassis, 1966 in 1966. Photo by Bettmann/Corbis

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.

Christopher Bailey

The most stylish businessmen of all time
Burberry's chief creative and soon to be president, Chris Bailey Photo by Getty

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.

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