Steve Jobs was the towering genius of consumer technology, the visionary behind what is still the most valuable company in the world. He was also the second-worst thing that ever happened to the turtleneck. 

He took an item closely associated with the greatest era of men’s fashion – the mid-20th century – and dragged it to Silicon Valley, which would, in style terms, be better known as Death Valley. Jobs’ uniform, Issey Miyake, in black, linked a proud piece of clothing with the idiotic tech-industry notion that appearance is a distraction from the things that really matter, namely (in ascending order) brains, money and power. Simplicity, casualness, fleece vests and normcore sneakers. Oh, the horror.

The turtleneck might have rebounded from Jobs’ influence were it not for his imitator Elizabeth Holmes, of the faketech company Theranos, who is first among the turtleneck’s abusers. She took Jobs’ core notion (the black turtleneck as an anti-decorative fashion statement) and associated it with her own core attributes. Now I suspect any wearer of being a wild-eyed megalomaniacal fraud.

Let us retake the turtleneck, then, starting with a roll-call of its great proponents. It is hard to think of any of the great dressers of, in round numbers, 50 or 60 years ago without thinking of their turtleneck moments. 

Jil Sander by Lucie and Luke Meier merino wool turtleneck, £620. Paul Smith light cashmere turtleneck (just seen), £400
Jil Sander by Lucie and Luke Meier merino wool turtleneck, £620. Paul Smith light cashmere turtleneck (just seen), £400 © Leon Mark

Miles Davis, cooler than ice in blues and browns. Samuel Beckett, looking austere in sweaters that emphasised his thinness. Richard Roundtree – yes, I’m talking about Shaft – managed to make a checked, possibly acrylic sport coat look dangerous by pairing it with a dark-brown rollneck and threatening sideburns. James Dean, in a dark turtleneck, pea coat and slept-in hair, radiated sex and, in retrospect, doom. 

Along with his red beanie, I think of Jacques Cousteau as a turtleneck man, and don’t we all dream of being Jacques Cousteau? He and Captain Haddock (what a perfect shade of blue!) have forever linked the turtleneck with adventures at sea. The young Bob Dylan made the connection to Greenwich Village coffee shops. Alain Delon made the turtleneck dreamy, sophisticated and Nouvelle Vague.

Berluti leather jacket, £5,750. Paul Smith cotton jacket, £450, and cashmere turtleneck, £215. Tod’s cashmere turtleneck (just seen), £450. Port Tanger acetate Ayreen sunglasses, £250
Berluti leather jacket, £5,750. Paul Smith cotton jacket, £450, and cashmere turtleneck, £215. Tod’s cashmere turtleneck (just seen), £450. Port Tanger acetate Ayreen sunglasses, £250 © Leon Mark

The absolute king of the turtleneck is the star of 1968’s Bullitt, Steve McQueen – still the man I want to be when I grow up. If I can’t have the Mustang, I’ll take the jumper. Derek Blasberg, a fellow turtleneck fan, agrees: “No one looked better in a high neckline than McQueen. Except maybe Michael Caine in Alfie. Or Paul Newman.”

All that history is a little intimidating. What is right for the contemporary mortal man? I think, with a few exceptions, one should avoid black. It is too fraught, and not just by Jobs and Holmes. There is a corny bohemian side to it too, redolent of hep-cats with bongos and berets. Finally and most dangerously, there is the tough-guy tactical-ops look, which is why we so often find James Bond in a black turtleneck. One of the hard rules of men’s style: always remember that you are absolutely nothing like James Bond. 

Jil Sander by Lucie and Luke Meier wool gabardine shirt, £640, wool trousers, £690, and sterling-silver heirloom necklace, £540. Berluti cashmere turtleneck, £760
Jil Sander by Lucie and Luke Meier wool gabardine shirt, £640, wool trousers, £690, and sterling-silver heirloom necklace, £540. Berluti cashmere turtleneck, £760 © Leon Mark

Men such as myself who are dealing with the serial humiliations of middle age will favour the turtleneck for concealing excess flesh around the neck. “Practically speaking, I love a turtleneck because it frames the jawline, which I’ve had a harder time finding while in lockdown,” adds Blasberg. But be careful: if a jowl overflows the top of your turtleneck, the result is not flattering (Gene Hackman, I’m sorry to say, had a bit of this problem with his otherwise on-point and off-white turtleneck in 1972’s The Poseidon Adventure). 

Turtleneck with a sports jacket or suit? Yes, just make sure the jacket has some texture to match the informality of the top. 

Where to shop? Major fashion houses are putting some muscle around turtlenecks for autumn, in a lot of nice colours. How about a dark-blue knit from Paul Smith? Miles would have approved. A mustardy, loose-fitting Hermès gets the 1970’s reference just right. And Prada has a pale-blue rollneck, if you have the complexion for it. 

Personally, I will be looking in vintage stores for excellent-condition woollen turtlenecks this season. A good sweater never really goes out of style anyway – as our list of icons proves. 

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