I bought my Sperry Top-Siders on a family trip to Texas in the spring of 2006. I remember them being on sale at some outlet mall we stopped at. Texas, outlet malls, discount shoes… I know what you’re thinking, and yes, my family does live in the lap of luxury while on vacation. But that’s not the point. My point is who knew five years ago such a purchase would leave a lasting mark on my life? My Top-Siders were not my first foray into prep style. (I mean, do you know me?) They didn’t leave a mark in that sense. More accurately, I left a mark in them — during almost all major milestones in my life since.
For starters, these shoes have traveled the globe with me. First on the streets of Buenos Aires, to the waterfalls of Iguazú, through the Andes-adjacent vineyards, and to the beaches of Uruguay. And now more recently on the streets of London, to the fjords of Norway, and to both the northern and eastern beaches of Spain.
They’ve made some major mileage stateside as well. They’ve accompanied me on friend visits from the east coast to the west coast and back again as I’ve made various pit stops in San Fran, NY, and Portland. And to the midwest coasts too — Minnesota and Ohio.
They’ve lived and worked in what I now consider to be my two hometowns, Madison and Chicago. And they also join me in every trip back to my actual hometown. They were on my feet at my graduation from UW and when I finished my Master’s here at UIC. They’ve even danced up a storm at multiple weddings of friends and friends of friends.
No other item in my closet is older than these shoes. Thanks to steady weight-loss over the years as well as a general cycling through styles, even staples of my wardrobe rarely make it past the three year mark. And although they’ve seen better days — both figuratively and literally — the longer I contemplate getting a replacement pair, the more unlikely it is that that’ll ever happen.
