How to dress like a menswear icon
Elegant, uncomplicated and, best of all, achievable – here’s how to dress like the titans of understated cool
The world of clothing is a place in relentless flux, an ever-evolving universe in which the telegenic move between labels, trends, Savile Row and Supreme with the fluidity of a Ferrari shifting gears. Between June and September, when you’re packing for the long weekend to Sardinia, the citybreak in Oaxaca or the Algarve beach escape, consider cutting through the noise by going back to basics and taking influence from our small selection of evergreen sartorial heroes.
Though this cadre of icons may have seen their burst of fame in the previous century, their legacy – namely the way they taught the world what it means to dress simply but well – belongs to the ages. For those moments when the toes are in the sand and the tan is lusciously deep and, more importantly, the style stakes are high, these are the masters from which to learn.
Steve McQueen
Perhaps the most bankable anti-hero in cinema, Steve McQueen is the closest thing Hollywood has ever got to starshine: powerful, vivid, indescribable. Of course, we could talk with great longing about his masterstroke roles in The Thomas Crown Affair and Le Mans, but we’ll always return to the way he never complicated the basics of dressing – the beauty he gave to a pared-down T-shirt, his penchant for great denim, the way he made Persols an item of pure lust. Pictured is the King of Cool on set, sporting an open collar, a Rolex Submariner 5512 slapped around the wrist, and box-office eyewear.
John F Kennedy
Power and style often go together, like politicians and dirty money, and it’s long been the case that the wardrobe choices of US presidents reflect the type of leadership they wish to project: the breezy cool of Bill Clinton with Wayfarers on his face and a sax around the neck, say, or the breath of fresh air that came with Barack Obama’s tie-less getup. Though John F Kennedy is historically feted for his sharp formalwear that ushered a feeling of youth and vibrancy into the Oval Office, it’s his off-duty trappings that get our vote – such as the configuration of preppy sailing staples he’s pictured in here.
Paul Newman
In the warmer months, playful, loud outfits can often take a man’s fancy, and you’ve likely thought about wearing high-fashion slides by the pool or expressive prints when heading out of town. But, for the risk-averse, we suggest pinning this image of Paul Newman onto your full-length mirror. This beachside getup – a combination of rolled-up jeans with plain sneakers, and an interplay of casual knit with formal shirt – is exactly what you should bear in mind when putting together an August wardrobe.
James Dean
James Dean, thanks to his gold-plated looks, was a linchpin of Hollywood’s glory days, and his skill at exercising raw and complex emotions in his roles made him into a mouthpiece for rebellious 1950s American youths. His knack for wearing menswear basics — V-neck jumpers, pea coats, Breton stripes — and a gravity-defying pompadour created a wildly successful cocktail that cemented him as a permanent fixture in best-dressed lists in the decades following his passing. This understated outfit, which is shown in Rebel Without a Cause, features all the necessities for winter days when the temperatures rise just a little: a fuss-free T-shirt; the iconic Harrington jacket; and great, great denim.
Sydney Poitier
It’s April 1964, and Sidney Poitier is both on top of a cluster of rocks in Central Park (as pictured) and on top of the world, following his Academy Award win for Best Actor — the first in the category awarded to a Black actor — for his role in the comedy-drama Lilies of the Field. “Up to the stage came the most elegant man I had ever seen,” recalled OprahWinfrey about the time when, as a 10-year-old watching TV, she saw the actor collecting the gong in a black tux jacket and white bow tie. Poitier largely drew attention for his understated but well-tailored ensembles — his ability to pull several layering pieces into a coherent whole was also key to his appeal. Which is where we return to the photo at hand, in which both notions come into play: here, we see a stretch of Manhattan apartments providing a backdrop for Poitier to pose against, triumphantly, weeks after his win, in a multi-pieced look where several contrasting details — striped tie against block colours, the light hue of the mac over a dark two-piece suit — provide numerous points of interest.
Carey Grant
The archetypal leading man, the North by Northwest star was blessed with all the graces, feted for his natural, easy style of acting, clean-cut face and hair so beautifully sculpted it appeared to come straight off a potter’s wheel. Throughout his time in front of the camera, he also made a name for wearing great formalwear that was as sharp as his barnet, with tie dimples and monochrome suits being his hallmarks. Here, however, he’s caught in a rare moment of casual dress, with the light hues of his shirt and wristwear (and salt and pepper locks) acting as the perfect foils to bring out the richness of his golden complexion.
Robert Redford
It’s hard to pinpoint what exactly the answer is — perhaps it was the prom-king-style flop of blond hair, or maybe it was the megawatts smile — but whatever Robert Redford wore in his prime years always seemed to have a vibrant, spirited feel to it. There was, of course, the perfectly cropped shearling coat in Downhill Racer, the jean jacket with contrasting cord collar in The Electric Horseman, and the moustachioed, western flare in Butch Cassidy and the Sundance Kid. All statement-making bits of costume design; all forever iconic. What we like in this picture, however, is the pared-down elegance; the ivory-white rows of teeth and the golden hair are indeed still there, but they’re anchored and kept in check by a dark, muted palette of smart-casual items.
Want more style content? We check-in with Kit Butler, the heir apparent to the British modelling throne…
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