As tweed is reimagined by designers from Saint Laurent in Paris to Tokyo’s Beams Plus, MR PORTER looks to the men who have worn it best.

For years tweed was tainted by its associations with the idler elements of the British aristocracy. As a result fashion designers neglected this venerable and masculine cloth, and the only tweed clothes available were old-fashioned and shapeless.

All that has changed, and there is a new world of contemporary tweed available, in cuts and textures that reflect our times. The image we aspire to is more downtown than Downton, as our weekends are more likely to include gallery visits than grouse moors. For key examples look to the elegant brown suit by designer Christophe Lemaire, or the details on a quilted Junya Watanabe field jacket.

For additional inspiration MR PORTER has drawn up a list of 10 tweed icons, each of whom has something different to teach us. From an early 20th-century architect to a 21st-century street style star, via rock’n’roll royalty, Hollywood royalty and real royalty, the icons are a varied bunch, but between them they offer a masterclass in how to wear tweed.

The visionary architect is elaborately dressed in this shot, adding a shirt with double cuffs to his spectacular three-piece suit. However, his charisma, the nature of the fabric and the cut of the jacket defuse any potentially off-putting formality. The heavily textured cloth, which is rich with rustic appeal, chimes with the soft shoulders and drape in the chest to give a relaxed, informal look. Three-piece suits will always make an impression, but worn like this the mood is dandyish, rather than stiff and self-conscious. Country-inspired clothes look their best during the day, so such an outfit could work well for a winter wedding, or a weekend lunch in a good restaurant. Wear it with polished brown brogues and a classic gold watch.

This Los Angeles-based designer has a determinedly casual West Coast image, which informs his Elder Statesman line of cashmere knitwear. As such Mr Chait brings a fresh approach to tweed and makes this soft Prince of Wales-check jacket serve his style by rolling up the sleeves, popping the collar and wearing it with a black T-shirt and dark chinos. Despite tweed’s rural history, and the fact that the Prince of Wales check has its 19th-century origins on the Seafield family’s shooting estate in the north of Scotland, Mr Chait demonstrates that its monochrome colour palette and its texture make it highly appropriate for informal city wear. Note that this jacket doubles as a coat, thanks to the buttons that run right up to the collar, and that it looks contemporary partly because it’s so short in the body.

The Rolling Stones singer reminds us that tweed jackets can just work as well on younger guys as they do on more mature men. The key, as Sir Mick knows, is to dress your age, which he achieves here by wearing his jacket with a simple black crew-neck sweater, rather than a shirt and tie. As such he avoids any formal associations while still looking presentable, and does so in a way that would today be particularly appropriate for a date. The jacket’s natural shoulders are soft and the flecked material conspicuous enough to ensure that no one thinks Sir Mick is on his way to the office. For such a casual style we recommend a man goes for a slim contemporary cut, a classic crew-neck sweater, a candle-lit bistro, a bottle of good red wine (Gigondas perhaps?), and that when his date arrives he remembers to stand up.

Photographed here in character in the 1975 conspiracy thriller Three Days of the Condor, Mr Robert Redford is more than just a great advert for losing touch with one’s barber. The bold salt-and-pepper herringbone weave on his jacket is masculine and timeless, and seems to owe at least as much to workwear as it does to professorial Ivy style. Worn with a sweater underneath it’s also substantial enough to serve as a coat, a versatility that’s as useful today as it was in the 1970s. Of course, it helps that Mr Redford wears it with an enviable chambray shirt, and the sort of woollen tie that’s both low-key and defiantly ill-suited to the office environment. Should you still be worried that tweed lacks raw appeal we can reassure you that, in the film, Ms Faye Dunaway seems to find it irresistible.

The French actor Mr Alain Delon looks remarkably serious for a man making a film (The Girl on a Motorcycle) with 1960s starlet Ms Marianne Faithfull; perhaps he was worried about the rights and wrongs of her wearing fur. Regardless of his mood, he provides us with a blueprint for how to dress up a tweed jacket. The grey colour makes the jacket right for town wear, while the structured shoulders give it a sharp look that’s business appropriate. Worn with an unpatterned pale shirt, a simple dark tie and a cashmere scarf, the look is sophisticated and grown-up. Mr Delon also demonstrates the ideal hairstyle for men who are past the age of hipsterdom but still have their hair, and the ideal relationship between shirt cuffs and jacket sleeves. It’s worth taking notice of both these things.

The film director Mr Wes Anderson is almost unanimously admired for his unique aesthetic, which is based on a modern interpretation of historic influences. Much the same can be said of his dress sense, which mainly consists of softly tailored clothes made from rustic fabrics. However, the effect, far from seeming precious, always looks appealingly relaxed. He’s photographed here on the set of The Grand Budapest Hotel, which was released earlier this year, and we note that he eschews a tie but wears eye-catching red socks and suede chukka boots. Mr Jude Law, pictured here in costume for the film, is in a far more mannered outfit, which consists of a sort of Norfolk jacket with elaborate breast pockets, a beige shirt and a pink tie. Much better, we think, to follow Mr Anderson’s off-screen example.

HRH Prince Philip, the Queen’s husband, here wears his sports jacket (the name reveals the garment’s informal past) in a way that is very specific to the British aristocracy. He was photographed at the 1968 Badminton Horse Trials, and is perched atop a bottle-green Land Rover Defender in a structured hound’s-tooth jacket, with a crisp pocket square, blue shirt, dark tie, pressed grey flannel trousers, long grey socks and, crucially, black leather shoes. It’s one of the near-unique quirks of the Duke’s wardrobe that he wears black shoes in the country, the one place where the vast majority of men agree brown is acceptable. The result is reminiscent of Mr Alain Delon’s urbane take on the tweed jacket, and in 2014 it seems more relevant for lunching in fancy restaurants than for watching live sports.

Famously dressed by Mr Giorgio Armani for the 1980 film American Gigolo, the actor Mr Richard Gere looks remarkably contemporary given how much else has changed in the intervening 34 years. By forgetting his tie, leaving his shirt collar open and adding an unexpected layer in the form of a faded pink zip-neck sweatshirt, Mr Gere sports a smart-casual look that would today attract the attention of the street-style photographers were he to turn up at Pitti Uomo. Mr Gere looks comfortable and at ease, everything he’s wearing looks soft and relaxed, and there are no jarringly formal or fussy details to distract from the whole ensemble. The jacket’s rough texture (the deployment of texture was one of Mr Armani’s great skills in his heyday) contributes to a vibe that seems creative, carefree and approachable.

In 1967’s The Graduate actor Mr Dustin Hoffman did almost as much for the image of the herringbone jacket as Ms Anne Bancroft did for the image of the older woman. At the time the jacket telegraphed the immaturity of Benjamin Braddock (Mr Hoffman’s character), in that he was still too young to adopt the suits that were then the uniform of grown men. However, the simple outfit Mr Hoffman puts together with the jacket – a blue Oxford cloth shirt and a dark knitted tie – now looks adult in a way that makes sense in all but the stiffest professional environments. Just add a pair of slim cotton chinos and brown Derby shoes, and keep a look out for any modern-day Mrs Robinsons as you go about your work.

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