Pronunciation:/ˈtʌɪmlɪs/
adjective
Not affected by the passage of time or changes in fashion.
Oxford English Dictionary
It is the reason why The Kennedys, The Rat Pack and Steve McQueen’s styles are still quietly envied today, long after they are since gone. At the opposite end of the spectrum, it is the same reason why photographs of footballers and today’s other modern “style icons’” clothing often looks clownish and outdated looked back at through the cold lense of a few years, or even just a few months’ distance.
Timeless style. Whilst some men are driven to be at the forefront of fashion, no matter what the trend or indeed whether it even suits them, others are quietly confident in their wardrobes, knowing it does not matter if their clothes were purchased last week or in the last decade.
With this in mind, MilanStyle.co.uk picks its favourite dressers from past and present who have mastered the art of timelessness. In no particular order.

The Kennedys: Collective Entry
Instantly recognisable as ‘American’ in their approach to style, The Kennedy brothers, John F. Kennedy and Bobby Kennedy (and of course, Mrs. Kennedy) modernised The Whitehouse, bringing an air of Hollywood to it for the first time. More on The Kennedy brothers’ style.

Prince Charles dresses in the true British / Savile Row style - double breasted suits, colourful silk handkerchief and double-cuffed shirts.
H.R.H. Prince Charles
Barbour, Burberry, Church’s, Tricker’s, Savile Row – many of these British institutions are often as old as the House of Windsor itself. It is not for nothing that several of these brands hold the Prince’s Royal Warrant, granted for providing him with their uniquely British ‘best in class’, function-first garments. Prince Charles – often topping the likes of GQ’s and Esquire’s famous Best Dressed lists (both American and British editions) has recognised that timeless dressing so often depends on ignoring trends and instead simply sticking to what works for you. He wore double breasted suits when they were not fashionable in the 80s and 90s. He wore skinny knots in his ties before the recent resurgence of the trend. He wore his British benchmade brogues by Tricker’s when the fashion magazines would only feature flashier Italian branded footwear – indeed it has been commented that ‘Prince Charles’ wardrobe never goes out of fashion, because it has never been in fashion’. This is a good thing.

Marvin Gaye
Whether it was simple, pared down suits in the 60s or ‘double denim’ in the 70s ‘What’s Going On’ era , this soul legend showed that true style comes from within, and always with soul.

The Chrysanthemum Throne: Collective Entry
Understanding the importance of continuity, Japan’s monarchy, the oldest in the world, recognise that simple but high quality clothes whether in the Eastern or Western tradition make the wearer seem as timeless as the monarchy itself. With the Japanese people placing a high value on heritage, honour and quiet dignity in their heads of state, the Imperial Household (Emperor, Empress and Crown Princes) realise that sober colours and an understated style add an air of dignity and confidence to their now largely ceremonial roles.

Motown: Collective Entry
Leading the way musically and sartorially in the 60s, Motown groups such as The Four Tops and The Temptations brought soulful style to the world with their slim suits, slim ties, small collars and co-ordinating outfits and showed the world what it meant to be suave.

James Bond
There have been countless in-depth books, magazines and blogs written about 007′s style. So, we leave you to discover and read those in your own time.
We only wish to add 2 points of our own.
1. TAKE NOTE: People who want to be taken seriously, whether they be fictional or real, understand the role that their wardrobes play in the making of their public image. When Bond is required to wear ‘black tie’ he wears traditional black tie. Understand this then. Leave ‘rule breaking’ and ‘your own spin’ at the door if you want to be taken seriously at a black tie or any other formal event. There are times when rules must be obeyed in order to be timeless – Black tie is one such time.
2. TOM FORD: Perhaps the best thing to happen to Mr. Bond’s wardrobe since Savile Row, Ford added an unexpected continental touch to the wardrobe of Britain’s most lethal MI5 Agent. A cautionary note however – not all men will be able to pull off pure white trousers.

Bruce Wayne
Known variously as a ‘billionaire philanthropist’, ‘playboy’ and ‘industrialist’, Bruce Wayne’s wardrobe is second to none. Labels in the last films include Giorgio Armani for formal wear, Belstaff for action wear and Sunspel for casual wear. Take note. You may not have his finances or his success with supermodels and Catwoman, but his style is one thing you can and should emulate.

The Rat Pack
Possibly America’s first mainstream interracial music group, similarly, each member had their own unique style. Today both Sinatra’s evening wear and Sammy Davies Junior’s ‘preppy’ style have stood the test of time and still inspire designers today.

Steve McQueen
An easy and common inclusion in these type of lists, it is with good reason that Steve McQueen still remains a ‘best dressed’ stalwart years after his death. Steve McQueen in his films and offscreen incorporated European menswear looks into his casual ‘American’ workwear wardrobe of brands including Lee and Wrangler alongside brands like Belstaff and Persol and seems to have had some sort of sponsorship arrangement with several European brands. He is also credited with featuring in the most stylish film of all time, The Thomas Crown Affair.
Finally, we leave you with the final words of two great designers…
“Classic, to me, is something that is timeless, enduring. The things that never go out of style. The kinds of clothes I design are the kinds of things I believe in, the kinds of things that last forever. I love things that stay.”
Mr. Ralph Lauren
“Fashion fades, style is eternal”
Mr. Yves Saint Laurent


