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Gianni Agnelli Style Lessons to Dress Like a Sprezzatura Icon

Gianni Agnelli’s fashion style is always the first topic of discussion in the Old Money style circle of connoisseurs, despite the Italian’s extensive work with fast cars and finest art.

The eldest son of Italian industrialist Edoardo Agnelli and Princess Virginia Bourbon del Monte and named after his grandfather, Giovanni Agnelli, the founder of Fiat, Agnelli had a quick wit, devilish charm, and elusive dressing style.

After taking over Fiat in 1966, Gianni Agnelli, nicknamed ‘L’Avvocato’ (‘The Lawyer’), moved in jet-setting circles and led a glamorous life packed with riotous parties, sleek yachts, fast cars, and luxurious villas.

But the Italian’s impeccable taste and (often eccentric) choices stamped his eternal footprint more in fashion than in business.

Not afraid to break fashion rules and create his signature looks, Agnelli’s style blended classic Italian elegance and flair, which became synonymous with his name.

From wearing his watch over his shirt cuff to leaving his button-down collars unbuttoned, Agnelli’s style was a testament to his confidence and individuality.

One of the most iconic elements of Agnelli’s style was his love for bespoke suits tailored by the renowned Italian tailoring house, A. Caraceni, in Milan.

Agnelli favoured classic double-breasted suits in timeless colours like grey and navy blue but also appreciated blazers and coats in tweed and flannel.

Accessories played a significant role in Agnelli’s style, with ties being a favourite as he wore silk ties with bold patterns, sometimes tucking them under his sweater for a more relaxed look.

His collection of luxury watches was also noteworthy, with brands like Omega being among his favourites.

Agnelli’s love for fast cars was just as renowned as his fashion sense. He owned an extensive collection of luxury vehicles, including Ferraris, Maseratis, and Lancias, which further added to his iconic status.

His close friendship with the Kennedy family, particularly John F. Kennedy, cemented his status as a global fashion icon.

Agnelli even hosted JFK and Jackie at his villa in Italy, a testament to his influence and connections.

Gianni Agnelli’s style continues influencing gentlemen worldwide today, from his winning combination of exquisitely cut classic suits to the distinctive personal touches of ‘sprezzatura.’

While Agnelli’s style was undoubtedly unique, modern gentlemen can incorporate elements of his look into their wardrobes without appearing outdated or overly eccentric.

The key is to balance classic old-money garments and personal stylistic touches to reflect your personality.

Gianni Agnelli’s Style Inspo

With meticulous attention to detail and the ability to make even the most casual looks appear polished and refined, Agnelli’s style blended classic Italian elegance with personal flair.

Here are some key elements of Agnelli’s style and how you can incorporate them into your wardrobe:

Wristwatch Over Shirt Cuff

Agnelli always wore his wristwatch, usually an Omega, on his shirt cuff.

While this became a distinctive style detail associated with him, it’s important to remember that people will think of Agnelli, not you, when you wear your watch this way.

If that’s how you want to be perceived, go for it; otherwise, consider alternative ways to showcase your timepiece, such as wearing it with a barrel cuff shirt.

Wear a sleek, contemporary watch over a crisp, tailored shirt cuff to modernise this iconic Agnelli move.

Opt for a classic watch brand like Rolex or Patek Philippe with a simple, clean face to keep it sophisticated.

Longer Back Blade Tie

In his later years, Agnelli consistently wore the back blade of his tie (the slimmer end) longer than the front blade (the wider end).

Most notably, neither end of the tie would reach beyond his waistband. Instead, he would tuck the long end into his trousers.

If you want to wear the skinny end longer than the wide end, do not extend either end beyond the waistband for a cleaner look.

Off-Center Tie and Tie Dimple

Agnelli wore his tie slightly off-centre, adding to his relaxed, sprezzatura style. Brands like Emma Willis, New & Lingwood, and Drake offer ties in various colours and patterns to help you achieve this look.

Agnelli wore a dimple in his tie, but it was never pronounced or perfectly in the middle. The way you wear your dimple is just another chance for you to create your look.

Unbuttoned Button-Down Collar

Agnelli wore his button-down shirt collar unbuttoned, even when he wore a tie. For him, it worked because he paired it with soft flannel jackets.

To adopt this style today, focus on one or two key elements of Agnelli’s style rather than trying to incorporate all of them at once.

Pair a high-quality Oxford shirt with a well-fitted blazer or sports coat, ensuring the collar has a good structure to maintain its shape.

Unbuttoned Sleeve Cuffs

Agnelli had his suits made by A. Caraceni in Milan and D. Caraceni and wore his sleeve cuffs unbuttoned.

However, with the widespread availability of working sleeve buttonholes today, closing one’s sleeve buttons is more understated and exclusive.

Instead of unbuttoning your sleeve cuffs, consider leaving your barrel shirt cuffs undone for a similar relaxed feel without appearing overly casual.

Slippers and Moccasins with Suits

Agnelli wore casual slippers, loafers, or mocs with a solid grey flannel suit to add a casual note to his ensemble.

When incorporating this style, choose a shoe that complements your suit and doesn’t appear too informal for the occasion.

Cheaney’s ‘Jackie III R’ chukka boots or Edward Green’s ‘Shanklin’ chukka boots are sophisticated options that can work well with a flannel suit while still channelling Agnelli’s style.

Popover Shirts

Agnelli was photographed wearing a white, three-button popover shirt, which Inglese supposedly made from Ginosa in Italy.

Since then, the popover shirt has become associated with Gianni Agnelli.

If you like the look of a popover shirt, it can be a good option for a casual shirt that maintains a polished appearance.

Grey Flannel Suits and Midnight Blue Tuxedos

Grey flannel suits were a staple in Agnelli’s wardrobe, most of them tailored by A. Caraceni in Milan using Vitale Barberis Canonico flannels.

His favourite shade was a mottled medium grey that became so popular that Vitale Barberis Canonico still produces it today.

Agnelli opted for midnight blue tuxedos and dinner jackets for formal occasions, a style that gained popularity among fashion connoisseurs in recent years.

When wearing a midnight blue tuxedo, keep the rest of your look classic and refined to avoid detracting from the impact of the colour.

By selectively incorporating these elements of Agnelli’s style into your wardrobe, focusing on quality materials, well-fitted garments, and a few key accessories, you can channel his iconic look while maintaining your style.

Remember, the key is using Agnelli’s style as inspiration rather than copying it, allowing your personality and character to shine through.

Gianni Agnelli’s Life

If one had to sum up Agnelli’s character traits in a few words, those would be charming, intelligent, curious, and stylish, as someone constantly searching for the perfect one-liner.

Agnelli always tried to brush away everything with a joke, thus shying away from emotional bonds with others.

For example, when JFK died, he said, “He was already screwed anyway,” referring to his troubled back.

He had no relationship with his children but instead enjoyed the company of women and life in general.

During his 40 years in power, he was the most important man in Italy’s economy, yet failed to groom a family heir.

Childhood and Upbringing

Gianni Agnelli was born into success and nobility; his grandfather, Giovanni Agnelli, propelled the family into affluence by co-founding Fiat well before Gianni was born.

His father, Edoardo Agnelli, continued the family’s growth as an Italian business magnate and principal shareholder of Fiat.

In 1919, formal nobility entered the family line when Edoardo married Virginia Bourbon del Monte, the daughter of the Prince of San Faustino, a member of the ancient Tuscan-Umbrian family.

The family’s entrepreneurial spark didn’t just transfer to Gianni–it grew throughout his childhood.

When he attended D’Azeglio High School in Turin, Italy, he developed an increased intrigue for business and the advancement of his family’s reputation, which he would later capitalise on.

Grandfather’s Influence

Unfortunately, Gianni’s life rapidly began to change in 1935 when his father tragically died in a plane accident at age 43.

Conflict arose between his grandfather and mother as Virginia became intimately involved with Curzio Malaparte, a writer and journalist, just a few months after her late husband’s death. In response, Giovanni attempted to gain parental rights for her seven children.

After his father’s death, Gianni’s grandfather moved to the forefront of his life and became extremely influential. Gianni wrote the following about him:

“[My grandfather] represented authority and absolute power. He was a powerful man in his city, a powerful man in Italy.

He was a very simple man and by nature a very influential man. And so, for me, he represented absolute power.”

He remained close to his grandfather from 1935 until 1940 when Gianni was pulled into the war that shook Europe.

Gianni Agnelli in World War II

Gianni served on the Russian and North African fronts during World War II, both of which came with their misfortunes.

On the Russian front, he was wounded twice, almost lost one of his fingers to frostbite, and endured even more punishment in North Africa as the driver of an armoured car built by Fiat.

It’s said that he got into an argument with a German soldier over a woman in a bar. Although he was shot in the arm, he managed to finish his drink before finally walking out.

After Italy fell to the Allied powers, Gianni acted as a liaison officer for the occupying U.S. Army.

American occupiers forced Gianni’s grandfather to resign from Fiat because the company built tanks for the war.

This, however, wasn’t Fiat’s worst fate because Giovanni already had a plan to deal with the transition–he placed the trusted Lieutenant Valletta in power to run the company until Gianni was mature enough to take control.

Gianni Agnelli’s Rise to Power in Fiat and Italy

Valletta remained in charge of Fiat until 1966, as Gianni Agnelli’s grandfather had intended.

At that point, Gianni Agnelli took control and started growing the business as he had intended to do since his time at D’Azeglio High School.

He led the company’s explosive growth by diversifying the business portfolio and expanding into countries such as Russia, Spain, and South America, moving into construction, finance, telecommunications, and media industries.

Gianni gained an extraordinary power boost from this diversification when it purchased La Stampa and Corriere della Sera, two of Italy’s most important newspapers.

Eventually, this strategy centred Fiat as Italy’s largest private-sector employer and, thus, a significant body of influence.

One of his fondest purchases was that of the Juventus Football Club, one of Italy’s most distinct football teams.

His family’s involvement with the club started in 1923 and continued, with Gianni personally running the club between 1947 and 1954.

Agnelli resigned from his hands-on leadership role due to health concerns but continued to own the club until his death.

He’s legendarily known for landing his helicopter at the training facility to chat with his players and calling the club’s president at 6 a.m. every morning.

Other notable conquests include his local acquisition of Alfa Romeo Lancia and a stake in Ferrari and Maserati.

In retrospect, his involvement in three of the world’s most famous sports car brands–Alfa Romeo, Maserati, and Ferrari—was a tremendous accomplishment.

Previously and politely rejecting Ford in the past, his absorption of Alfa Romeo had all the more significance since the American motor company had already been eyeing up the Italian brand.

However, many controversial deals were made during his time in power, including a deal with Colonel Qaddafi in the 1970s.

During the international petrol crisis, Gianni decided to sell part of his company to Qaddafi’s Lafico to ease the blow of the troubled economy.

Ultimately, Gianni would buy his shares back back once the situation improved.

Another famous deal was reached when he sold 20% of the car business to General Motors in the early 2000s.

Gianni Agnelli’s Role in the Italian Economy

Gianni and Fiat’s influence on the Italian economy was extraordinary.
He’s credited with moving Italy from an agriculture-centered reliance to an industrialised nation.

Before his influence and actions truly set in, about three-quarters of the Italian population lived on the land.

The country continues to credit his business acumen with Italy’s rise from absolute poverty to becoming the world’s sixth richest state after World War II.

It’s also whispered that Gianni owned a quarter of the shares on the Italian Stock exchange during his lifetime.

During its prime time, Fiat supplied 50% of Italians with their vehicles and was the icon of industrial success and style.

The Uncrowned King of Italy

Gianni’s tremendous stake in the Italian economy through Fiat, dinners with the world’s most powerful people, and his country’s admiration granted him the “Uncrowned King of Italy” title.

Italians used to say, “Agnelli is Fiat, Fiat is Turin and Turin is Italy” to express his influence on the state of affairs.

Another common nickname was L’Avvocato (lawyer) because he studied law but never practised it.

At one point, an anti-corruption crackdown erupted in Italy, removing most of the country’s corrupt influencers but Gianni’s reputation remained untouched, solidifying his title of the “Uncrowned King of Italy”.

Gianni Agnelli’s Women

Agnelli lived the life of a playboy, with notable mistresses including Linda Christian, Danielle Darrieux, Rita Hayworth, and Pamela Churchill Harriman–the former wife of Winston Churchill’s son – some would add Jacqueline Kennedy to his list.

Gianni lived in a 28-room villa in southern France, where he spent five years with Pamela Churchill Harriman.

While Pamela enjoyed the relationship and even described it as one of the happiest periods of her life, it hit a rough patch in 1952 when she found Gianni with Anne-Marie d’Estainville.

While allegedly driving d’Estainville home, Gianni got into a terrible car accident that damaged one of his legs so badly that the doctors thought they might have to amputate it.

His affair with Pamela fizzled out soon after, and he was quoted giving the following advice about women: “There are men who talk of women and others who talk to them–I prefer talking to them.”

Gianni Agnelli’s Only Marriage

After a series of affairs, Gianni settled down by marrying the Neapolitan Princess Marella Caracciolo di Castagneto.

According to the official Gianni Agnelli website, he said the following about her:

“Marella? We have lived together for a lifetime. At that point, the other person becomes a part of you; how can we call ourselves friends? It’s more, much more, it’s part of you.”

Known for her tall and classical features, Marella continues to stand out in history as a fashion icon in her own right.

Admitted to the International Best Dressed List in 1963, Marella became a Hall of Fame Member with a fashion portfolio including studying in Paris, working with the photographer Erwin Blumenthal in New York, contributing to Vogue, and developing her capsule collections.

More recently, she oversaw the grand opening of the Renzo Piano-designed Giovanni and Marella Agnelli Art Gallery in 2002 to prepare the country for the Olympics.

The marriage didn’t stop Gianni from getting involved with other women, but the marriage remained intact until he died in 2003.

Interestingly, Agnelli responded in one line when asked about being unfaithful:

“You could be a good husband and fool around, or a very bad husband and be fidel.”

Agnelli’s Art Collection

Gianni balanced his love for cars and beautiful women with an interest in art.

His priceless collection included Italian Futurists, four Monets, and pieces by Klimt, Bacon, Warhol, and Lichtenstein.

After he died in 2003, the collection was donated to his hometown of Turin.

Attempted Assassination

Although a man constantly in the public eye, Gianni consistently rejected the notion of having bodyguards around him even though terrorists were gaining serious power in Italy.

One captured terrorist recounted a story of how he had Gianni in his crosshairs but was unable to get off a clear shot.

The Death of Gianni Agnelli

On January 23, 2003, Gianni Agnelli passed away in Turin at the age of 81 from prostate cancer, and every news outlet in the country covered the news.

To give some more perspective on the significance of this event, Italy’s leading newspaper devoted its first 19 pages to Gianni.

There’s a saying that a man’s importance can be measured by the number of people at his funeral, further proving Gianni Agnelli’s impact on the country and the world around him.

Over 100,000 people, including the president and prime minister, gathered at Fiat headquarters to see his body, followed by an applauded procession through the streets.

The influence of the bespoke-suited Gianni Agnelli and contributions to modern fashion, business, and culture has remained strong since his passing in 2003.

Adapt Agnelli’s Style by Occasion

Smart-Casual – wear a tailored navy blazer, classic dark blue jeans, an Oxford shirt, and Penny loafers. Complete with a pocket square for a touch of Agnelli-inspired flair.

Formal – wear a white shirt with a patterned tie, monk straps, and a classic double-breasted grey suit to channel Agnelli’s love for this style.

Business-Casual – Tuck a slim knitted tie under a fine cashmere sweater and pair it with tailored trousers and monk strap shoes.

By understanding and selectively incorporating these elements, readers can channel Gianni Agnelli’s distinctive style while making it their own and ensuring it fits seamlessly into modern capsule wardrobes.

Remember, the key is using Agnelli’s style as inspiration rather than copying it, allowing your personality and character to shine through.

Fashion Brands Embodying Agnelli’s Aesthetic

Brunello Cucinelli

This brand captures the luxurious yet effortless style that Agnelli was known for. Look for their tailored blazers, soft cashmere sweaters, and elegant trousers that blend comfort with sophistication.

Loro Piana

Known for its high-quality fabrics and understated elegance, Loro Piana offers pieces that reflect Agnelli’s penchant for luxury. Their outerwear and knitwear, in particular, align with Agnelli’s refined yet practical style.

Tom Ford

Tom Ford’s sleek, tailored suits and bold accessories mirror Agnelli’s ability to combine classic and contemporary elements. Look for their sharply tailored suits and eye-catching ties.

Canali and Ermenegildo Zegna

These Italian brands offer classic, tailored pieces that align with Agnelli’s sophisticated look. Their attention to detail and use of high-quality materials make them excellent choices for those seeking to emulate Agnelli’s style.

Master Sprezzatura with The VOU

Knowing Agnelli’s style and life is one thing; however, knowing how to apply sprezzatura according to your colour palette, body shape, and fashion style is a form of art you can also master.

You get that by ordering one of our styling packages for men; a complete Fashion Styling package identifies your ideal colours and garments for your body shape, curated from heritage brands.

Imagine walking into a room and turning heads for all the right reasons, or picture yourself radiating self-assuredness and sophistication, knowing your sprezzatura is on point.

We’ve helped countless men like you elevate their style and achieve the much-coveted silent luxury style, so don’t hesitate to contact The VOU’s stylists right now for a free introductory class.

With over twenty years of front-row fashion and styling events, collabs with haute-couture houses, and a PhD in Luxury Fashion, Laurenti is an expert in crafting personalized looks that depict old-money sophistication.

With years of expertise in high-end fashion collabs and a PhD in Sustainable Fashion, Ru specializes in curating eco-luxe wardrobes for the modern gentleman seeking understated refinement.

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