The fashion writer Derek Guy -- perhaps best known for his pithy menswear observations and advice, dolled out via X -- talks us through his sartorial favourites, from David Hockney to Njideka Akunyili Crosby

If one were to pinpoint the single most significant theme of 20th-century fashion, it would be the shift in dress influence from individuals with financial capital to those with cultural capital. This switch meant that people no longer only looked to the aristocracy for dress direction; they also drew inspiration from rocker rebels, blue-collar labourers, members of various counter-cultural youth groups, musicians and artists.

This has made style harder to emulate. The dress habits and preferences of the ruling class can be broken down by colour, cuts and fabrics (partly because they all bought their clothes from the same tailors and their dress was governed by time, place and occasion). But with creative types, rule-breaking is the norm. Many artists also have that mysterious quality called "the eye". Still, their style inspires, so writers continue to try to pin down what made their fashion choices so alluring. Here are ten artists whose sense of aesthetics was expressed even through their wardrobe.

Pablo Picasso

Despite being familiar with English tailoring, it was when Pablo Picasso (above) was at home, hidden from the public eye, that the artist looked his best. He was a strong proponent of loose-fitting casualwear to beat the heat in his Mediterranean environs. He wore thick-striped Breton-style pullovers with brown plaid bouclé trousers; cherry-red terrycloth polos and espadrilles; and rumpled white linen shirts with barely there shorts. "Those who attempt to explain a picture are on the wrong track most of the time," he once said. His style is proof that the most important thing you can do in dress is to train your eye, not memorise rules.

Andy Warhol

Classic American tailoring declined after the Second World War because it was too closely associated with the establishment and no one wanted to appear as though they would defend Watergate. Yet Andy Warhol often looked like he had just stepped out of Brooks Brothers. He wore natural shouldered, three-roll-two seersucker suits, navy blazers, red bow ties and rep-striped four-in-hands, Ivy-styled two-button jacket cuffs next to his Cartier Tank watch, and Waspy L. L. Bean barn coats over Oxford-cloth button-down shirts. Perhaps he always looked cool in these clothes because of his talent and persona -- or maybe because his outfits were a little off-kilter.

Duncan Hannah

Sitting in his Brooklyn apartment, Duncan Hannah was once interviewed while wearing a navy Yale appliqué sweater with raw denim jeans and a pair of brown leather camp mocs. "I've basically ignored the avant-garde," he said. Although he was speaking of his paintings, the same can be said of his wardrobe. The boyishly handsome artist didn't dress like your typical, tortured New York painter, but rather like that class of blue-blooded Americans found on pages written by John Cheever or Louis Auchincloss. Despite running in counter-cultural circles, Hannah looked very much like the mid-century American Establishment -- and he did it without an ounce of irony.

Georges Braque

The German art dealer Daniel-Henry Kahnweiler considered Georges Braque to be something of a discreet dandy. "He used to wear very simple blue suits, of a wholly distinctive cut, the like of which I've never seen," he recalled of the artist. Those suits were something of a cross-breed between French workwear and British tailoring. They were constructed from utilitarian materials but there was no structure underneath, so they draped like the bleu de travails that French labourers wore in factories. The work of an artist isn't the same as a labourer's, but Braque purloined some of the pieces and turned something utilitarian into a creative expression.

Georgia O'Keeffe

Georgia O'Keeffe's wardrobe had a streamlined spareness. She wore Turkish trousers, Japanese wrap-style fronts and monastic dresses, almost always in black. She relied on custom tailors such as Kniže in New York for black pantsuits and K.C. Chang in Hong Kong for floor-length overcoats. She even made her own clothes such as a black-and-white dress decorated with streaming ribbons, which she sometimes teamed with her signature wide-brimmed hat. O'Keeffe wanted to dress distinctively but not necessarily to shock people. She did so by stripping away colour and detailing, allowing her to focus on the most important part of an outfit: the silhouette.

David Hockney

Eccentricity in dress works best when you're more interesting than your clothes. This is why David Hockney is able to treat dress rules with such contempt. The artist is just as famous for his chaotic outfits as he is for his paintings. He fearlessly smashed genres together, teaming sweatshirts and sneakers with tailored suits before the combination became a fashion cliché. Beneath his mop of bleached blonde hair often sits a pair of thick-framed glasses, a floppy knitted necktie and colourful socks -- sometimes matched, sometimes not. A Savile Row tailor once asked Hockney how he achieved his wonderfully rumpled look. Hockney answered: "I don't own any hangers."

Alberto Giacometti

Alberto Giacometti was one of the few artists in 1950s Paris who still wore tailored clothing, even when he was elbow deep in clay. He often had some kind of neckwear -- if not a tie then at least a jauntily knotted small scarf. According to his biographer, James Lord, the artist wore "the clothing of male respectability", but the clothes were always loosely cut, beaten up and never too pressed or polished. They had an aged softness that prevented them from looking bourgeois. "Alberto's apparel was so much a part of his personality as to seem almost a state of mind rather than an outfit of clothes," Lord wrote. His deliberately dilapidated style reminded viewers that he was still an artist.

Jean-Michel Basquiat

It's possible that style can be inherited because Jean-Michel Basquiat had it in his blood. His father Gérard was always impeccably dressed, but they had a difficult relationship, which is perhaps why the artist forged his own identity and didn't dress with his father's conservative sensibility. Yet he still couldn't shake that familial sense for style. Jean-Michel wore dramatic knee-length overcoats that swished when he walked, slouchy double-breasted suits that he insouciantly fastened in the wrong position, and floral-patterned pullovers that he paired with red tartan trousers. There was something about his outfits that felt perfect but impermanent, much like his graffiti.

Njideka Akunyili Crosby

Artists often dress in ways that distinguish them from the rule-bound bourgeoisie. By contrast, Njideka Akunyili Crosby's personal aesthetic is not counter-cultural but rather chic. She wears short black shifts, floor-sweeping dresses and patterns reminiscent of her home country, Nigeria. Much like her paintings, there are often layers of multicultural meaning; she once showed up to an interview wearing her husband's t-shirt with a pair of jeans and a silk scarf wrapped around her head in the traditional Nigerian manner. She demonstrates how simple accessories can draw the viewer's eyes up to a person's face, making the wearer the focal point of an outfit.

Frida Kahlo

It should be no surprise that Frida Kahlo was interested in the semiotics of clothes, as she wore a man's three-piece suit and slicked back her hair for a family photo in 1927, making herself look androgynous during a time when it was still controversial. For much of her life, she favoured indigenous items sourced from Mexico and Guatemala: a rebozo (shawl), square-cut huipil blouse and voluminous enagua skirts trimmed with handmade lace to celebrate Mexico's matriarchal Tehuantepec people. Kahlo used clothing to express her identity, reaffirm her politics and beautify her disabilities. Like paint to canvas, she used clothes to create a masterpiece: herself.