The best dressed man in the world, according to Esquire Magazine. One of the most photographed gents in menswear and street style. A great inspiration for myself and for thousands of others who follow him on Instagram. A fashion entrepreneur (founder of Alessandro Squarzi Showroom) and a regular at Pitti Uomo, where he represents his clothing brands, Fortela and AS65. “The master of Italian sprezz”, as Tommy Ton once put it… Mr Alessandro Squarzi himself.

To me, he represents the cream of the crop when it comes to men’s fashion – classy and handsome in a suit, but also confident and comfortable in sneakers, sweatshirts and white pants. And most importantly, genuine. A very good definition of a modern gentleman.

I must admit I’ve started this page, Talks – Conversations with menswear icons having this interview in mind.

Alessandro Squarzi: “I think being successful means having many responsibilities towards others. My team is like family to me and I take care of my family.”

Alessandro Squrazi / Talks by Silviu Tolu
Photo by Hywel Jenkins

ST: Mr Alessandro Squarzi, what an honor! Thank you for taking the time. Would you please tell us what a regular day in your life looks like?

AS: I don’t speak to anyone before having had breakfast. I truly wake up only after my first espresso of the day. If I have time I like to go for a walk or a ride on my bike before heading to the showroom or to meetings. I don’t really have a standard day, but I like it like that!

“I have always described my style as GipsyClassic: I am very attached to my classic roots but I like to combine them with my passion for vintage and military.”

ST: Can you give us some background info like how did you get started in the world of men’s fashion and if this is something you’ve always dreamed of doing?

AS: I am living the dream of when I was a kid and I am so grateful for that. I started working in the fashion field in a menswear store in my home town.

ST: What does being successful mean to you?

AS: I think being successful means having many responsibilities towards others. My team is like family to me and I take care of my family.

Alessandro Squarzi / Talks by Silviu Tolu
Photo by @thestreetfashion5xpro for Vogue Italia

ST: What does style mean to you? How would you describe your style?

AS: To me, style is not just about the clothes you wear but mostly about your attitude towards life and others. I have always described my style as GipsyClassic: I am very attached to my classic roots but I like to combine them with my passion for vintage and military.

ST: You have great aesthetic sense. Where do you get your inspiration from?


I think aesthetic sense is innate. You are either born with it or not.

Maybe I get mine for being a Libra: as far as I know it’s considered the most aesthete among the signs of the zodiac.

ST: You are very passionate about vintage. What does it represent to you?

AS: When I was little I didn’t have money to buy new, expensive clothes so I used to buy vintage ones. I have learnt more and more about it over the years up to the point that vintage has become not only a passion but also the focus of my two apparel lines AS65 and Fortela.

What a wonderful day.. #alessandrosquarzi #asstyle #gipsyclassic #aslive #fortelastyle @fortela_ @jacquesmariemage @vans

A post shared by Alessandro Squarzi (@alessandrosquarzi) on

ST: Do you have any daily habits or rituals that help you being productive and/or creative?

AS: Actually I don’t, I’m not a creature of habit. It depends, day by day.

ST: Any tips or advice on how can someone develop a cool personal style?

AS: Never dress to follow a fashion but always based on your own physique and what looks good on you.

ST: You’re going to a friend’s birthday party. What are you bringing as a gift?

AS: A bottle of good wine to drink together or a Hermes table ashtray.

ST: What is a clothing item that every man should own?

AS: A pair of white pants.

ST: Who is the first person you think when you say Iconic?

AS: My dad.

Alessandro Squarzi / Talks by Silviu Tolu on
Alessandro Squarzi’s picks for the Talks moodboard

ST: You definitely have plenty to choose from, but… what is your favorite watch?

AS: The Patek Philippe 3970 in yellow gold I bought when my daughter Allegra was born.

ST: Your car collection would make any man jealous: Defenders, G Class, Porsches… What is your favorite? How about motorcycles? Any other models you’d like to collect?

AS: Unfortunately I have sold many over the years because I have less and less time to enjoy them. But my absolute favorite remains my Porsche 356 Speedster nicknamed Rossina by Allegra. My dream motorcycles would be a British Vincent.

ST: Your favorite clothing item?

AS: My white jeans and my 1950s Buco leather jacket.

ST: Where does a man find proper jewelry (rings, bracelets, necklaces)?

AS: Depends on one’s personal taste… I, for instance, like Navajo jewelry and the best place to find it is in Santa Fe.

ST: What’s your go-to cocktail?

AS: My absolute favorite cocktail is an Americano.

ST: Who is your female inspiration?

AS: Lauren Hutton and my daughter.

Alessandro Squarzi / Talks by Silviu Tolu
Alessandro Squarzi and his daughter / Photo by Mr Scott Schuman (The Sartorialist)

ST: If you would be stranded on an island and you could pick one book (fiction or non-fiction), one music album and one personal item, what would these be?

AS: Book – Shantaram by Gregory David Roberts;

Music Album – everything from The Rolling Stones;

Personal item – my inseparable pocket knife.

ST: Your home, in Rimini if I’m not mistaken, is your sanctuary. What are other places you like traveling to?

AS: I love going to Saint Tropez where I have a wonderful apartment. The other places where I like traveling to are NY and Tokyo: I have many friends over there and I truly feel at home in those cities.

ST: What are: the best restaurant in Florence, the best coffee shop in Milan, best vintage shop you’ve ever been to?

AS: Best restaurant in Florence: La Vecchia Bettola and the restaurant of the JK Place Hotel.

Best coffee shop in Milan: Pandenus and Ceresio 7

Best vintage shops: Cherry Vintage in Florence and Fortela’s vintage selection in Milan.

Soon you will see it with the shutter open! #alessandrosquarzi #asstyle #gipsyclassic #aslive #fortelastyle @fortela_

A post shared by Alessandro Squarzi (@alessandrosquarzi) on

ST: What are your plans for the future?

AS: I promised Allegra I would take her to live in Montecarlo…

ST: And lastly, is there anything you’d like to promote on this page? It can be an idea or a quote, or anything at all you’d like to share with the readers?


True elegance is not found in the clothes you wear but in your manners.


Thank you very much, Mr Alessandro Squarzi and good luck in everything that you’re doing!

Alessandro Squarzi / Talks by Silviu Tolu
Photography by Mr Bill Gentle for Mr Porter

Alessandro Squarzi / Talks by Silviu Tolu
Photo by Matteo Bianchessi