What makes certain men more stylish

I always curious when I read lists announcing “the most stylish men in the world”.

It makes me wonder how you quantify the stylishness of an individual.

I’m often asked who I think are the most stylish men and who has inspired me and my style. I often mention Paul Newman and Steve McQueen; I can’t believe there is a man alive today that wouldn’t have wanted to be either of these inspirational men Paul and Shark Shorts for sale.

For me, those two individuals were and still are the definition of a man. They were incredible actors, but they were also outspoken individuals who weren afraid to speak their minds. They also loved racing cars and bikes, weren afraid to have a few drinks and did a tremendous amount for charity. But first and foremost they were always themselves. Paul Newman once said: me a man without enemies and I will show you a man without character.”

But would I call them my style inspirations? No. This may sound confusing, but the more you read about them, the more you learn that they were not actually very interested in style. Apparently Paul Newman once burnt every bit of clothing he had apart from a pair of trousers and a shirt, as he said that this was all he needed. If you delve into the outfits that these guys wore, they were sometimes comical, style-wise, but because of the people they were, with their confidence and inherent coolness, their powerful characters made whatever they wore instantly stylish.

They didn’t have stylists, of course, they were utilitarian dressers first and foremost. They dressed themselves in what was required for that specific occasion. When riding a motorcycle or racing a car, they wore a T-shirt and Belstaff or Barbour jacket, as these were the best products at the time. These they matched with racing watches and sunglasses – not because this was a trend, but because these items were the most appropriate for the job. It’s only subsequently, and thanks to the association of people like McQueen and Newman, that Belstaff and Barbour jackets, Tag and Rolex watches and Persol sunglasses became style “essentials” for aspirational men.

When it comes to my most stylish men, there are a few criteria that appeal to me.

Firstly, I always wonder whether they are naturally stylish or if they have been styled by someone else. Famous guys obviously have a huge choice of brands and designer clothing available to them and they also have the choice of some of the top stylists in the world if they like to employ their services. Sometimes the two go hand in hand: a well-known man might choose to style himself with the help of a stylist who will source the clothes on his behalf. But for those who go from having awful dress-sense to being style personified overnight, this isn style in my book. It doesn make a person stylish, it simply the work of a great stylist.

Buying expensive clothing isn a shortcut to being stylish either. A stylish man can put a £10 pound T-shirt together with more expensive items if he has a good eye. His entire outfit might be made up of non-designer clothes, and he will still look sharper than a guy wearing an outfit five times the price if he has his own well defined sense of style.

It often the small details that can make a huge difference and set the men apart from the boys, from the colour of a watch strap to a man’s shoes. Being individual and not caring about what other people think is important to me when thinking about personal style, rather than following trends or the crowd.

Perhaps style is in the eye of the beholder, but for me it’s a blend of knowing how to dress to suit your own shape and personality, individualism, confidence and character. On that basis, here (in no particular order) are my top five most stylish men.

Lapo Elkann

Lapo Elkann (Photo: Rex Features)

Elkann is the grandson of former Fiat chairman Gianna Agnelli (a style icon in his own right). He is an entrepreneur and has worked with Fiat and Ferrari, and although often named as one of the most stylish men in the world, I’m sure most men probably won’t know of him. Lapo’s style is always based around Italian tailoring and flair. He is never underdressed for any occasion, he doesn’t follow trends or ‘styling rules he goes against the grain and puts together textures, patterns and colours that basically shouldn work, but they do. Everything is carefully thought through; the width of the lapel, the socks, the shoes, the eyewear. It certainly isn’t conservative, but I think that the brilliance of his style. He clearly doesn’t care about what other people think, he dresses for himself, he’s an individual. I had the pleasure of meeting him in Milan last year. We talked about cars, not fashion, and he was a true gentlemen. Compared to him, I felt rather underdressed.

Harold Tillman

Harold Tillman pictured with Samantha Cameron in 2012 (Photo: AP)

Harold Tillamn is an English entrepreneur and investor and until September 2012 he was also the Chair of the British Fashion Council. For me, Harold is the definition of a true British gentleman. If you want to know how to make tailoring work for any occasion then Harold is the man you should research. I cannot imagine there is a man in the world that wears or styles a suit better than him; not even Prince Charles (who is another style icon of mine). Again, it the detail that matters to him; the right tie with the right collar; the right shoes for the suit. I met Harold many times and there isn one occasion that I have seen him wearing anything out of place. He wears British tailoring like no other man can. He also has a great car collection!

Ryan Gosling

Evan Rachel Wood and Ryan Gosling in The Ides of March

Ryan Gosling may work with a stylist, I don know, but he has that old-school Hollywood look, charm, talent and charisma that is often missing from today world and it this that gives him individualism. His effortlessness in how he dresses makes anything he wears instantly stylish, just like McQueen and Newman. He looks great in suits and often he’s quite daring with them, but actually it his casual style that I admire the most. It looks effortlessly strung together, but if you look closely, he knows what works for him – T shirts are always low crew necks, his sunglasses and shoes are always impeccably stylish, everything is thought through and he is always well groomed.

James Dean

James Dean (Photo: EPA)

You might ask how I can have James Dean on here when I not included Paul Newman, McQueen or Cary Grant. Well, James Dean was around for so little time before his tragic death, but in that short time gave us so many iconic images and styles that I think if he was around today, he would surely be known as the most stylish man ever. Maybe I’m wrong, but I think James Dean cared and thought about his style, from the deep V-necks and his driving gloves, to the sunglasses and full length coats in that iconic Dennis Stock shot of him in NYC in 1955. Of course, he also loved driving, owned a car collection, and loved racing his Porsche. Maybe I biased – there seems to be a pattern emerging here!

Andreas Kronthaler

Andreas Kronthaler with his wife Vivienne Westwood (Photos: Rex Features/AP)

Andreas is Design Director and husband of Vivienne Westwood. I interviewed him for my Style App and I have to say out of all the people I have met, he has been my biggest inspiration. He doesn’t hold back with his opinions and is brave to state his thoughts honestly; probably held by many, but perhaps spoken by few. He told me once that when he goes on holiday or on a business trip he carries a few outfits, just in case anyone is wearing anything similar to him. I suppose you can’t get any more individual than that! But apart from being a true individual with his style, he ticks many other boxes. He takes a lot of creativity from tailoring, often separating suits, mixing with T shirts or with denim. His attention to detail is impressive; he mixes vintage and contemporary designs better than anyone I know but for me, his biggest appeal is that he is a true gentlemen. He never shouts about his achievements, of which there are many, one being that in style terms he is one of the most forward-thinking men in the world. There just one problem: I don’t think he has a car collection.