I realized I was obsessed with the best Madewell tote ever made when I spent an August in Italy with friends a few years ago. A friend and I rented a villa for a month and hosted rotating groups of our besties in the Florentine suburbs, in the town of Marcialla, population: 300. With that as our home base, we drove to see the Palio di Siena, dined at Michelin-starred Linfa in San Gimignano, posed with the Leaning Tower of Pisa, and many other activities that, as I think about it now, make me dearly miss the rolling hills of Tuscany and those cypress trees that pierced the pale blue sky. But there’s one thing I remember most clearly about that trip, mainly because it was featured in almost every single photo my friends took of me: a bulging yet fabulous leather satchel attached to my right hip: The Madewell Zip-Top Transport Tote.