The entrepreneur and street-style icon reveals the stories behind some of his most treasured timepieces.

Menswear designer, entrepreneur and keen-eyed magpie for all things vintage, Mr Alessandro Squarzi has more than 400 watches. That is, well, rather a lot. But he had a little help to get to this prodigious number. “I had an uncle who had a rather nice watch collection,” he says. “When he passed away, he left it to me. I was very young at the time, but there was something I liked about it, so I continued to grow the collection.”

Mr Squarzi is a consummate collector of all sorts of things “that have a story behind them”. This ranges from clothes, to pens, to his enviable line-up of vintage cars. It’s something of a talking point among those who know him well. “My friends always say: ‘Ale, that’s enough! You have too much old stuff,” he says.

Whatever his friends think, we at MR PORTER are thrilled Mr Squarzi has amassed such a treasure trove of exceptional pieces – especially his watches – because it gives us a good excuse for a trip to the beach to have a look at them. For the above video, in which he explains some of the stories behind some of his favourites, we joined Milan’s most photographed man at his home in Rimini, where he keeps most of his most prized possessions, or, as he calls them “toys”. “When I come home to Rimini, I switch off everything and leave everything behind,” he says. “I switch off the noises and this creates a silence which lets me listen to the sea.”

Click play on the video to see some choice pieces from Mr Squarzi’s watch collection – from a time-weathered Rolex to the Patek Philippe he bought to commemorate the birth of his daughter – or scroll down for the text version.

Find out more at MR PORTER’s Luxury Watch Guide

IWC Pilot’s Watch Mark XVI Ref IW3255-01

“The IWC Mark V [of which the Mark XVI is a descendant] is a watch that British pilots used to wear, so it’s a watch that has a military background. If I’m not mistaken, it was standard equipment in the RAF. So it very much suits my passion for things that have a story – even if it’s a watch that’s new it’s still part of that group of things that I like enormously.”

Omega Ultra Thin Ref OT3980

“This is a replica of the Omega that JFK used to wear. Omega produced a limited edition of 261 pieces [to commemorate Kennedy’s inauguration as US President in 1961] – mine is number 47. It was given to me by my wife Alessia when we got married. Inscribed on the back is the dedication ‘I Love You’. It’s very beautiful and elegant and I like wearing it, especially with a dinner jacket or a suit.”

**Rolex Submariner Ref 5512 **

“This watch I care hugely about because it was worn by my father for many years. I persuaded him to give it to me and now it is one of the watches I wear on a daily basis. Over time, the watch face turned from black to caramel – a defect that has made it more distinctive, and adds value. My father still asks me ‘When are you going to let me wear it a little bit?’ as he too is very fond of it.”

Patek Philippe Ref 3970

“If I ever had to suddenly flee and save just one watch, it would be this Patek, which I bought when my daughter Allegra was born. The desire to have Allegra was immense as she was a really wished-for child and I had been saving up to buy this particular watch, so I tied it to her birth. So for me this watch has a wonderful history, it has no price, it is unsellable. One day I shall hand it on to her.”

Omega Seamaster Chronograph Ref 176.007

“This Omega Seamaster is one of the watches from the collection my uncle left me. It’s not an especially valuable watch, but its size and the shape of the casing is very 1970s, which I really love. This one has a blue face that really stands out. These tones of blue and the orange-coloured hand give it this distinctive colour of the 1970s.”

Jaeger-LeCoultre Reverso

“Whoever collects watches and has a passion for them has to have a Jaeger-LeCoultre. The Reverso is in my opinion one of the watches of the 1920s. And in the 1920s it was just as it is now with this casing that turns over. The wonderful thing about the Reverso is that when you order one you can have inscribed on the back of the face any dedication you want. In this particular instance, I had my initials inscribed.”