The Milan-based fashion entrepreneur and street-style regular takes us on a sartorial trip through his home city .

Mr Alessandro Squarzi first became acquainted with the fashion media in 2009, when street-style photographer Mr Scott Schuman published a picture of him on The Sartorialist. It was the start of a strong friendship between the two. “We are now great friends,” says Mr Squarzi. “When I’m in New York, I’m often to be found at his house. And the same goes for him when he’s here in Italy.” Now the focus of many a fashion photographer’s lens, Mr Squarzi’s American-influenced, elegant approach to dressing is much admired by street-style snappers such as Mr Tommy Ton, who once described him as “the master of Italian sprezz”. A regular fixture in MR PORTER’s On The Town line-up, Mr Squarzi is nothing short of a modern style icon.

His style credentials were not obtained by accident. Mr Squarzi has always worked with clothes, and is a prolific fashion entrepreneur. He oversees the marketing and distribution for various brands (including three of his own – Fortela, AS65 and Atlantic Stars) from his Milan showroom. And, like all good success stories, he began at the bottom. Born into a working-class family in Forlì in 1965, he started his career in 1992 as a shop assistant in a clothing store in the city, which he describes as “a fertile training ground”. That same year, he opened his first showroom. He has since launched four more across Italy and now employs 40 staff. “I have always worked as an agent, but with that entrepreneur’s mentality, buying up stakes in companies which showed potential,” says Mr Squarzi.

With salt-and-pepper hair and a permanent smile stretching across his face, Mr Squarzi says he adores his work, but his true love is Allegra, his 10-year-old daughter. He brims with paternal joy as he tells us, “She is strong-willed, and if she wants to follow me into this trade, then I’ll certainly back her up.”

From his tailor to his favourite restaurant, Mr Squarzi takes us on a tour of his Milanese haunts, and reveals what he likes to wear from MRPORTER.com and his own wardrobe. Read his style advice (including the acceptable hem length of his trademark white trousers), and shop his wardrobe below.

At home

Mr Squarzi opts for comfort when he is at home in Milan’s multicultural Porta Venezia district, one of the historical gates into the city, matching some Converse All Stars with his trademark white trousers, which he wears irrespective of the weather. “I never look out of the window before getting dressed,” he says. “I just put things on according to the mood I’m in.” And he is pleased to note that his influence has reached the Far East. “Up until a few years back, very few people wore [white trousers], but now it is something I notice in all my Asian clients,” he says, his voice revealing just a hint of pride. If he’s heading out, he likes to slip on a camel-coloured coat, such as this one by Theory. He completes the look with a vintage Filson bag.

His favourite watch is a Rolex Daytona 6263, which he acquired when he was starting out in his career. Having saved up for months, he chose it after realising he couldn’t afford the Submariner he really wanted. “It was a fortuitous coincidence,” he says with a chuckle. “That watch is worth far more today, and its sentimental value is priceless.”

Mr Squarzi enjoys trying his hand – with varying degrees of success – at photography. He uses a Leica M6. “It’s one of my passions, which I picked up from a photographer friend,” he says. “But I still have a lot to learn.”

**The Alessandro Squarzi showroom  **

The pace is frenetic in Mr Squarzi’s showroom on Via Spartaco, especially during sales campaigns. At work, he swaps his white trousers for dark blue jeans, and the All Stars make way for a smark pair of black Derbies. Refusing to forgo comfort, Mr Squarzi likes to wear a white T-shirt, a dark blue sweater and a blue cashmere coat, such as this one by Acne.

For a board meeting, he says he would wear white jeans and a pair of slippers or sneakers. “Unless an invitation specifically requests a suit, I wear whatever I feel comfortable in at that given moment,” he says. Dress codes are to be respected, he believes. It is simply good manners to do so. This is something that was drummed into him by his father, a style icon of his, alongside the legendary Italian actor Mr Marcello Mastroianni, Mr Steve McQueen and Mr Paul Newman.

Mr Squarzi has always had a weakness for neck scarves, one of which is pictured above. “I collect them on my travels,” he says. His passion for vintage pieces began when he was a young boy, unable to afford designer brands. He would head to the market in Montagnola, near Bologna, in search of second-hand Levi’s, “the ones that still had the selvedge; worth a fortune today”.

A. Caraceni atelier

In Milan, Mr Squarzi gets his clothes made by Mr Carlo Andreacchio at A. Caraceni on Via Fatebenefratelli. “They are the cradle of men’s bespoke tailoring in Milan,” he says. To make this suit, he picked two flannels by Fox Brothers & Co, the British cloth manufacturer founded in 1772. For suit fittings, Mr Squarzi opts for a pair of Belgian loafers, black jeans by Maison Margiela, a white tuxedo shirt and a suede jacket.

Mr Squarzi is also not averse to Neapolitan tailoring: “My wedding suit was made up by [Cesare] Attolini.”

But his favourite tailor is an 82-year-old man known enigmatically as “Alfonso”, who is based in the city of Rimini. Even though he has retired, Mr Squarzi managed to convince him to keep making his clothes. “I believe it is an art form, and as such it fascinates me and commands my total respect,” says Mr Squarzi. “Now his name has been mentioned in numerous Korean and Japanese magazines,” he says with a smile.

Rotonda della Besana

“The secret of my success? Nothing is contrived,” says Mr Squarzi, when asked about this look. “I dress this way for Pitti events and runway shows, as well as for my private life, like when I am at the Rotonda della Besana with my daughter after I pick her up from school.”

In the rare moments he’s able to relax and read the paper in the grounds of this baroque landmark, Mr Squarzi might wear a blue suit – such as this one by Paul Smith – double monk-strap shoes, a light blue shirt and a blue overcoat.

L’Arabesque

“I’ve only been living in Milan for a few years, and this place has become one of my mainstays,” says Mr Squarzi of the restaurant in the Largo Augusto area of Milan, where he is a regular. “I often meet friends or even clients here to close a deal.”

Today, Mr Squarzi is wearing a military green jacket and a grey sweatshirt with white Nike Classics. He breaks up the look up with some striking red socks. At the age of 51, Mr Squarzi appreciates that clothing has the ability to conceal the signs of ageing, and opts for a more comfortable fit. He likes trousers with a single pleat and a hem width of 19cm.