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AS YOU ARE holding a copy of Esquire in your well-manicured hands, I’m going to assume you understand a thing or two about looking smart and put-together. But what about looking dishevelled and elegant at the same time? Not so easy.

Dishevelled elegance is an advanced sartorial state, a tricky-to-master style involving skew-whiff ties, half-popped collars and rolled trouser legs. To be clear: this isn’t scruffy dressing. It might appear like a wardrobe accident, but it’s all about precision and detail. In the wrong hands, it can look as though you got dressed in the dark; done properly, it’s quietly devastating. Get acquainted – you’re going to see a lot of dishevelled elegance this season.

It all started in June when, six days before his Dior Men’s debut, Jonathan Anderson teased a famous Andy Warhol Polaroid of Jean-Michel Basquiat on the brand’s Instagram grid. Basquiat wears a grey blazer, chambray shirt and striped tie, but what makes the image remarkable is the total disorder of his collar and knot. For Anderson, it perfectly cued his summer 2026 collection of romantic dandies and Etonian fops – but what was Basquiat thinking back in 1982?

Was it a mini act of rebellion, subverting the codes of menswear? A blink-and-you-miss-it middle finger to tradition? Or did he just oversleep? A smarter writer might draw parallels with how Basquiat challenged the stuffy Uptown gallery establishment with his graffiti-influenced paintings – but this isn’t ArtReview. Whatever the motivation, it was a stroke of genius that conveyed an aristocratic attitude to clothes: undone, lived-in, zero-fucks-given. Basquiat is too cool, too busy – or too busy being cool? – to care. Except, of course, he really cares. And that’s the tightrope walk of dishevelled elegance: pulling off nonchalance without looking like you’re trying. Sorry, Italian friends, but this is where so-called sprezzatura – cue no socks and double-strap monk shoes – goes horribly wrong.

Basquiat wasn’t the only artist to get dishevelled elegance right. Warhol always offset his conservative uniform with a haphazard twist: a multi-pocket utility jacket thrown over his cord blazer, Brooks Brothers shirt and tie; or jeans and cowboy boots worn with a dress shirt, bow tie and tuxedo jacket at the 1977 Met Gala. In paparazzi shots, he looks as though he left the Factory in a hurry and got suited and booted in the back of a limo – no time even to straighten his wig – yet he always appears effortless. Peter Beard and Robert Mapplethorpe also dabbled in the straight-from-the-studio aesthetic, though their Hollywood-idol looks did much of the heavy lifting.

Peter Beard
style, men's style
Robert Mapplethorpe

For my money, David Hockney is the ultimate poster boy for dishevelled elegance. Mismatched socks, off-centre ties, tousled hair, crumpled trousers, cock-eyed bow ties, mis-buttoned cardigans, rugby shirts with double-breasted blazers… Hockney has always been fearless, in a Paddington-meets-Gatsby kind of way. With tweed suiting, he even
made yellow Crocs look good.

Francis Bacon and Lucian Freud pioneered a more extreme version of the look that, for my taste, veered into chaotic shambles. Honourable mentions go to Hockney’s friend Patrick Procktor, who perfected what-day-is-it dressing, and to contemporary practitioners Harland Miller, George Rouy and Luke Edward Hall, all of whom look ultra-stylish no matter how paint-splattered.

style, men's style
Avalon

So, this summer, to hell with looking polished. Slick isn’t it. Mess it up — but remember: dishevelled elegance is a fine art, so learn from the masters.

This article first appeared on Esquire UK

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