Best-Dressed Men Of All Time

Posted on 16/03/15

Funnily enough, we’ve reeled off iconic leather jackets and jacket wearers on this blog, but overall looks are a stone we’ve somehow left unturned.

OK so for this next line to have the most impact, you need to adopt your best trailer voice. Maybe even a Clarkson-like reading would be nice – we’ll leave it up to you. Just… Maybe leave your producer out of it…

Any road up, here we go. Eh hem “…a stone we’ve somehow left unturned”.

…Until now.

Joking aside, we wanted to put the spotlight on men who consistently impress when it comes to fashion, whatever the season and whatever the occasion. Here, we’ll list our ten best dressed men of all time, each with their own signature style and sartorial trademarks that anyone can adopt in their own way.


David Beckham, footballer

David Beckham


Despite some suspect fashion choices in his younger years (the less said about the sarong, the better), David Beckham has evolved into one of the most stylish men on the planet. Equally capable of pulling off motorcycle chic and formalwear, he rarely makes a misstep, and leather jackets frequently feature in his ensembles.

He’s worn a number of styles of jacket over the years, whether it’s a classic or asymmetric biker, or a traditional bomber or multipocket jacket. As such, replicating Beckham’s look can become a tad complicated…

Get the look: You can replicate Beckham’s leather looks with either the Hale (our classic biker jacket), the Mottram (our asymmetric biker), the Altrincham (our traditional bomber) or the Knutsford (our multipocket classic).


Edward VIII, former Duke of Windsor & King of England

Edward VIII


The original royal trendsetter was the (brief) King of England, Edward VIII. Although his reign on the throne never really got out of the starting gate, his fashion choices live on. Fond of checked patterns, cufflinks (an inscribed pair of his diamond cufflinks sold at auction for £115,000) and an incredibly high standard of tailoring, we can all learn something from his outfits. Let’s not forget that Eddie 8 (which is probably what his friends called him, right?) is the namesake for the Windsor tie knot as well, which is nice we suppose…

Get the look: Idumenti dark blue and light blue check suit


Tom Wolfe, author

Tom Wolfe


Admittedly, there aren’t many authors known for their sartorial flair, but Tom Wolfe is a striking exception. The author of Bonfire of the Vanities has been donning crisp white suits with matching ties, homburgs and two-tone shoes since 1962. It’s a brave look, one that might be a bit much to pull off all year round, but it’s undoubtedly one that forces you to sit up and take notice.

Get the look: Brooks Brothers white linen suit


John F. Kennedy, former President of the United States

John F Kennedy


While politicians these days aren’t allowed to be tremendously expressive in their fashion (there was uproar when Barack Obama had the nerve to conduct a press conference in a tan suit rather than the typical navy, black or grey affair…), JFK in his heyday was, and still is, the most stylish president of the lot. Brooks Brothers were the main clothing supplier to the White House during his presidency, though his suits were always tailor-made and his casual style was always classically ‘preppy’. His off duty wardrobe comprised chinos, penny loafers – maybe boat shoes if he was out on the Kennedy family yacht – and crew neck jumpers.

Get the look: Orlebar Brown dive blue polo shirt


Jean-Paul Belmondo, actor

Jean-Paul Belmondo


One of the major figures in the French New Wave cinema movement in the 1960s, Jean-Paul Belmondo’s style made him the picture of indifference with respect to fashion. It was Belmondo’s look that hammered home the idea that sometimes it’s not clothes that make the look necessarily, as it is the way one wears their wardrobe. A rumpled suit, a pair of driving moccasins and a cigarette were all that Belmondo needed to fully embody French street style. Would anyone else be able to pull off the same ensemble quite as well? We’re not sure we could, but as shown above, he also knew when to clean up his look with chinos and button-down shirts – something which we’re almost positive we could pull off.

Get the look: Corneliani slim-fit taupe chinos


Miles Davis, jazz musician

Miles Davis


Certain items of clothing become synonymous with certain men. They become signature pieces that work for any occasion and never go out of style. Miles Davis had a lifelong addiction to G.H. Bass & Co. Weejun penny loafers, as well as his trusty trumpet of course, and he invariably teamed them with straightforward slim-cut trousers and an Ivy League-esque upper layer (a blazer or jumper with an oxford shirt). Functional and stylish to a T, his sartorial preferences mirrored his trumpet playing – ahead of its time.

Get the look: G.H. Bass & Co. tan Fenmore Weejuns


Marcello Mastroianni, actor

Marcello Mastroianni


If you thought black suits were for funerals only, let Marcello Mastroianni, the star of La Dolce Vita convince you otherwise. Throughout the film he wears the everloving hell out of a slim fitting black suit, topping it off with a white French-cuffed shirt and a slim black tie. It’s a look that once again demonstrates the importance of a suit’s cut. It mirrors Mastroianni’s body time perfectly, and as such, it looks as though he was born to wear it, as though it was designed specifically with him in mind. Which to be fair, it probably was… Film budgets and all. Nonetheless, it’s a level of fit that all men should aspire to when buying suits, cardigans… Anything, really.

Get the look: Emmett London slim double cuff white shirt


David Bowie, legendary musician

David Bowie


There are very few men who can wear absolutely anything and look incredible in it, but David Bowie is one of those gifted few. From his early days as the androgynous Ziggy Stardust through to the sharp suits that characterised his look in the eighties and beyond, Bowie has never succumbed to style over substance. He looks fantastic, performs even better and has been influencing music and menswear for more than five decades. It would have been a travesty not to include him in this list, frankly.

Get the look(ish): Etro check pattern single-breasted jacket


Steve McQueen, actor

Steve McQueen


Any man looking to wear basic pieces well should take a good long look at Steve McQueen’s style. From t-shirts and aviator sunglasses to shawl-collared cardigans and jeans, McQueen was the master of looking fantastic with simple clothes. Get the silhouette right, along with a mix of textures appropriate for the weather, and it’s extraordinarily easy to replicate his style.

Get the look: J.Lindeberg navy shawl collar cardigan


We’ve only looked at nine men this time, but we could easily revisit this in the future. The same goes for best-dressed women too, we’re not sure where our blogging endeavours will take us next, but to keep up to date with blog posts as soon as they go live, you can follow us on the usual social media offenders (Twitter and Facebook, mostly).

Recent articles