Five men’s fashion tips from Gianni Agnelli – the iconoclast who did things his way

They say that in order to break the rules, you must first know them.

Having grown up as the privileged scion of one of Europe’s most prominent establishment clans – the proprietors of automotive giant Fiat, intermarried with aristocracy and considered the “Kennedys of Italy” – Gianni Agnelli certainly understood the strictures of decorum in behaviour and dress. Nevertheless, this iconoclast chose to flout convention and do things his own way.

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A famous playboy of the Dolce Vita era and prolific serial philanderer who was known as “The Rake of the Riviera”, Agnelli was also a one-of-a-kind style icon, living and dressing entirely as he pleased, bourgeois conservatism be damned. Agnelli, a new documentary premiering on HBO tonight, celebrates Agnelli’s life and style – including these trademark rebellious menswear moves.

1. All the right buttons?

A tailor will tell you, when wearing a double-breasted suit coat, the interior “jigger” button should be fastened, and generally only the uppermost exterior button done up. Certainly, never let a double-breasted jacket hang haphazardly unbuttoned, they will gravely admonish.

A confirmed enthusiast of double-breasted suiting, Agnelli utterly disregarded the jigger, often left his jackets hanging open, and when he did deign to do them up, normally used the lower button. So wrong, yet so right. He also habitually left the collars of his Brooks Brothers oxford cotton button-down shirts flapping in the wind – raising questions as to why he bought button-down collar shirts at all.

2. Off the cuff

Agnelli was well known for wearing his watches over his shirt cuff. He explained that the metal of his timepieces irritated his skin, and besides, being busy running a multibillion lire conglomerate (at one point, the Fiat group accounted for almost five per cent of Italy’s GDP and employed three per cent of its workforce), he simply didn’t have the time to peel back his sleeve to check the hour.

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3. Shoe business

It’s common enough today, but in Agnelli’s mid- to late-20th century prime, wearing moccasins with a suit was an audacious move. Sporting driving shoes not only hinted at the owner of Alfa Romeo, Maserati, Ferrari and Fiat’s passion for automobiles, but also his power, acting as a potent symbol that much of Agnelli’s life was spent quickly skipping between the cockpit of a supercar and a plush padded carpet. No pounding the pavement for this cosseted tycoon.

Conversely, he also pioneered wearing hiking boots with suits, contrasting the smoothest of Italian bespoke tailoring – most of it crafted by A. Caraceni of Milan – with the most rugged of footwear.

4. Double or nothing

If wearing double denim is a fashion crime, Agnelli was guilty as charged, a remorseless repeat offender. Spending many of his casual moments clad in head-to-toe in denim, coupling western shirts with soft-washed “dad jeans”, never has this supposed faux-pas looked so effortlessly stylish as when channelled by Agnelli.

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5. Hanging loose

Wearing his ties artfully askew, the back blade free from the constraints of the rear “keeper loop”, Agnelli evinced the sense of studied nonchalance that the Italians refer to as sprezzatura. During the winter months, he would often let his tie drape over the top of a V-neck jumper. And this wasn’t the only area where he would let it all hang out.

Frequently skinny-dipping from his 95-foot yacht, Sincerity, Agnelli was captured repeatedly by the paparazzi leaping nude from the sloop. The vast inheritance he received from his father wasn’t the only large endowment Agnelli was gifted with.

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His predilection for brazen nudity notwithstanding, as a menswear icon, his influence has been huge.