The prolific neo-expressionist of the 1980s was also known to be a singularly stylish individual with eccentric tastes. Seen here at the height of his fame in 1986, Mr Basquiat’s combination of a checked sport coat with a pair of jeans, printed button down and thin tie demonstrates a nonchalant approach tailoring and what is considered “smart clothing”. The jacket thrown on just so, worn like a cardigan or overshirt rather than occasionwear, therefore opening up more interesting wardrobe opportunities than the run of the mill white shirt-and-tie look.

With his popularity increasing from his early work as a graffiti artist on the subways of New York, Mr Keith Haring’s colourful animated drawings and imagery were always politically and socially underpinned. He tackled some of the most pressing issues of the 1980s.

Beyond that, Haring understood the power of self-representation. His style, as seen here at a fashion show in 1988, took cues from early street culture and incorporated elements from sportswear and a mash-up of conflicting graphics. It’s an energising way to add a bit of character to what can otherwise be a sober outfit.

Having a personal uniform that becomes a part of your identity can be surprisingly liberating. By saying no to the boundless options of fashion, you can just get on with life.

Take the artist Mr Joseph Beuys. By establishing a simple working uniform of felt hat, heavy cotton white shirt, fisherman’s vest and dark jeans, his focus was purely on his art. It also gave him an iconography of his own. Beuys’ uniform, while grounded and practical, was distinctive. A believer in shamanism, the felt hat was like a totem, while serving the practical purpose of covering scars from his time as a rear gunner during WWII.

Beuys’ thought-out approach to clothing allowed him to occupy a variety of spaces without ever looking out of place, which ultimately is what you want from something you’re going to wear for the rest of your life.

As the first Black artist to be elected a Royal Academician, Sir Frank Bowling is hailed as one of the greatest living abstract expressionists. In a career that spans more than 60 years, the British-Guyanese painter and sculptor experimented with colour, light and shape, and in doing so asserted that Black artists need not be confined to political or social work because of their race.

Still a natty dresser today at the age of 89, Bowling in his younger days cut a particularly sharp figure. Seen here in his New York studio in 1967, when he embarked on his famous Map Series, the artist’s collarless striped cotton popover makes a case for easy shirting in the warmer months. Especially when worn slightly roomier, to achieve a silhouette that is almost blousy. With its wrinkled hem and rolled-up sleeves, Bowling’s number exudes an enviable relaxed confidence.

Ms Georgia O’Keefe was a keen observer of the natural world. She used colour and abstraction to get to the essence of a plant, the skull of a cow or the desert landscape of her New Mexico Home, yet her personal style was rigorous to the point of severity and almost always rendered in black or white. According to The New Yorker, she once said that her decision to dress so plainly was born out of practicality. If she spent all her time picking out what colours to wear each day, when would she paint? Her emphasis on silhouette is instructive, too – shapes that stand away from the body and create a distinctive line.

Mr Richard Hamilton, a pioneer of pop art whose work often included elements from comic strips and advertising, understood the value of mass media, so it follows that he’d gravitate towards denim, the great equaliser.

Everyone loves and owns a pair of jeans, but wearing denim from head to toe is still regarded with a modicum of suspicion (blame the 2001 American Music Awards). The key to wearing it right, as Hamilton demonstrates, is to embrace the fabric’s utilitarian roots and to keep it simple. Looking at ease in his north London studio in 1970 in patchwork jeans and a well-worn western shirt, his unprecious approach feels entirely modern half a century later.