Street Style

The Motorcycle Diaries: Rupert Sanderson on the Trip That Changed His Life

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Traveled to Italy for the first time in 1999, at the tender age of 33, when I was enrolled in a two-year shoemaking course at a technical college in East London. I made plans to ride my friend’s Triumph Thunderbird motorbike through the northern cities—Milan, Parabiago, Bologna, Florence, Santa Croce, Arezzo, and Vermezzo—to see factories, specialists, and tanneries…pretty much as many people, places, and things associated with shoes [as possible]. An Italian classmate helped me create an itinerary using a way-out-of-date directory of factories I found in the college library. He contacted the factories on my behalf, so I just assumed they were waiting for me, but it turned out that none of them actually expected me to visit. Looking back, the arrangements were sketchy, but each place was very welcoming. It took about a month to hit all the stops—including the most extraordinary concert of my life, Tom Waits, whose performance at an opera house in Florence blew me away. Gaining a technical understanding of the vivid and visceral process that real shoemakers practice helped me realize my dream of becoming a designer who creates, rather than simply designs. It was a life-changing trip.”

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