5 of the best dressed men in business

Take note from some of the world's most successful - and stylish - gentlemen

To be sartorially on point throughout all aspects of life – not just on the weekend – is important. Dressing well shows a sense of self and proper ambition. You’d never catch the CEO of a global cooperation in jeans and a t-shirt on Monday to Friday, would you? So, when it comes to office dressing, these are the gentlemen worth looking up to. They are consistent, sharp and never seen without so much as a pocket square out of place. These, gentlemen, are some of the best dressed men in business.

Tom Ford

His directorial debut in A Single Man was one of the most stylish films of the 21st century; his fashion empire is one of the most successful in the business and he’s the type of man that, no matter how much effort you’ve put into your outfit, will always make you feel automatically scruffy. Enter Tom Ford, gentlemen, the man who’s rarely seen without a slick black suit and his trademark white shirt, whose weekend wear is nicer than most of our everyday wear and who always, always makes the most sartorially sound decisions.

Christopher Bailey

Before Bailey came onboard at Burberry, the company had little credibility. But with a strong sense of the industry and a firmly screwed-on business head, Bailey climbed to the top of the fashion world – where he still firmly sits. Not only has he become one of the most respected gentlemen in fashion, but also one of the best dressed. Obviously, Bailey tends to wear Burberry most of the time – and as expected, he wears it well.

Lapo Elkann

You’d be forgiven for recognising Elkann as a street style star rather than one of the most successful men in business – he is, after all, Gianni Agnelli‘s grandson. But his day job at the helm of Fiat means that fashion only comes second to his work. Known for breaking the boundaries when it comes to personal style and taking it almost as seriously as his 9-to-5, Elkann is undoubtedly one of the most stylish gentlemen in business. Klkann has cited some of his favourite pieces as a tuxedo he with collaborated with Gucci on, as well as a pair black alligator and corduroy boots – “versatile enough to wear with a suit, jeans and chinos, and on my motorcycle.”

Luca di Montezemolo

During his time at the helm of Ferrari, di Montezemolo was seen as one of the best dressed men in the world. And now, years on, he still runs the show both sartorially and throughout his entire business. Rarely seen without his suit and tie, di Montezemolo’s Italian style represents stylish businessmen the world over. He’s cited Tod’s as his favourite shoes, for both work and for play; for his timepiece he either heads to Patek Philippe or a Hublot and his suits are made by a bespoke tailor with a Northern Italian Silhouette.

Stephan Winkelmann

We see a pattern occurring here – most of the best dressed businessmen work with cars – and Stephan Winkelmann (the president of Lamborghini) is absolutely no exception. Always smart, but with an edge that is often hard to come by in a business sense, Winkelman stands out from a rather populated crowd and does so with serious style. Winkelmann wears dark or striped business suits, and prefers a keyhole buttonhole in his lapel. He normally goes for a white shirt and white tie and is never seen without a big, bold watch.

Further Reading