From a sporting start to a weekend winner – we track the history of one of our favourite (but unfortunately named) wardrobe regulars.

Sweatshirt. Let’s take a moment to say the word out loud. Sweatshirt. Sweat. Shirt. Hardly the most appealing name for a garment, is it? Yet this humble scrap of jersey cotton has managed to outgrow its athletic origins – not to mention its off-putting name – to become an essential part of the modern man’s wardrobe.

The blueprints for the sweatshirt were laid down in the 1920s by the Alabama-based sportswear manufacturer Russell Athletic, which developed it as a lightweight alternative to the itchy woollen football jerseys that were typical at the time. It’s the same quality that made the sweatshirt such a hit on the sports field – namely, comfort – that has eased its transition into the casual wardrobe.

Essential, by the way, is not a word we toss around lightly. In this case, however, we think it’s entirely justified. In the same way that a vinyl collection wouldn’t be considered complete without a couple of albums by The Beatles, so a wardrobe is hardly a wardrobe without a sweatshirt or two. In celebration of this enduring favourite, we’ve picked out one classic example and highlighted a few men who have worn it well.

The sweatshirt has been the subject of numerous high-fashion reinterpretations over the years, many of which can be attributed to Givenchy’s sportswear-loving creative director Mr Riccardo Tisci. For the purposes of this story, we’ve decided to steer clear of rottweiler prints and leather trim. The one we’ve chosen is by Sunspel, a British brand known for its cool simplicity and irresistibly tactile cotton and fabrics. In a light grey marl (a thread spun from two different colours of yarn) and often with that distinctive, spongy V-insert at the neck, it’s the gold standard for a sweatshirt and the very first one you should buy, especially if you’re planning on following in the footsteps of these famous men.

Not monarch material, as it turned out. But what Edward VIII lacked in kingly virtues he more than made up for in personal style. Here he is in 1953 enjoying a round of golf and a cigar while dressed in an outfit that, while it probably wouldn’t have met the exacting sartorial standards expected of a British head of state, certainly satisfies ours. Oh, and if you’re looking to ape the style of the Duke of Windsor – always a good idea – then opt for a soft-collared shirt, as he has. The less stiffness and starch, the better. In fact, you could do worse than wear it with the first of our Essentials, the blue Oxford shirt.

Funny how things come around, isn’t it? Ten years ago, wearing this particular shade of pale blue denim would have earned you an atomic wedgie at school. Now, it’s the toast of the cool kids in Dalston, Williamsburg and Neukölln alike. One thing that never went out of style, though, is the sweatshirt. In this shot from 1984’s Footloose, Mr Kevin Bacon, whom you might recognise from the parlour game Six Degrees of Kevin Bacon, gives us a great example of how to wear it in a slightly more contemporary (by which we mean post-ironic retro fashionable) way.

The rise of modern, breathable, sweat-wicking sportswear has somewhat robbed the sweatshirt of its original purpose. Think about it. When was the last time you saw someone actually sweating in one? Terrible shame, and not just because cotton sounds a lot nicer than polypropylene mesh. Here’s Mr Elvis Presley in 1962 – back when he still worked out – modelling the sweatshirt in its natural habitat and looking fantastic while doing it. Note the diagonal seam of the raglan sleeves, which are stitched from armpit to collar for added flexibility. Could we see a revival of the sweatshirt as gymwear? On the evidence of this photograph, MR PORTER sincerely hopes so.

For anyone experiencing a sudden sense of déjà vu, yes, we did feature Mr Paul Newman in last month’s edition of The Essentials, and yes, it was on the set of the same movie. And no, we’re not sorry. Few men in the 20th century were so consistently well-dressed as Mr Newman, and the effortless off-duty style he’s channelling here was his stock in trade. Blue Oxford shirts, grey sweaters… he could do ’em all. What’s of note in this particular image, then? Apart from the obvious (hello, Heineken), there’s something quite glamorous about the impracticality of dressing entirely in grey and beige, if only because it lends you the air of a man who doesn’t have to concern himself too much with laundry.

Try, if you can, to draw your gaze away from a fresh-faced and very hungry-looking Ms Jane Fonda – in her first film role, by the way – and onto the lanky frame of Mr Anthony Perkins. The year is 1960 and the two young actors are on the set of Tall Story, a romantic comedy in which Mr Perkins plays a college basketball star who is relentlessly pursued by Ms Fonda’s predatory home economics major. As was the case with Mr Presley, this is yet another example of the sweatshirt in its natural habitat. Like the Chuck Taylors Mr Perkins is wearing on his feet, you can see exactly why it became such a crossover hit.