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Most boys don’t know how to dress for rush. I didn’t, at least. Sorority recruitment comes with mood boards and “get ready with me” videos, but fraternity hopefuls have to rawdog it. Unless their moms buy them something new at the end of summer, they just wear their “going out” clothes from high school. This is how I went to my first fraternity party in boat shoes.
Even though my Dallas all-boys school sat at the foot of the Great Plains, most of us wore Top-Siders. As early as fifth grade, kids dressed like they wanted to go northeast for college. To supplement our uniform, we wore Harvard/Yale/Princeton sweatshirts, Vineyard Vines belts, and Sperrys. A lot of boys had the tan leather ones, kicked in like a baseball glove. At lunch, they played lacrosse at half speed so that their feet and mid-calf socks wouldn’t fly out of their shoes.
The origin of the Top-Sider is even more Waspish than I could’ve imagined back then. Paul Alling Sperry grew up in Connecticut, Manhattan, and France and attended Taft and Dartmouth. His family’s ties to New Haven go back to 1644. On a cold day in the 1930s, as the story goes, he watched his cocker spaniel, Prince, run across icy terrain, and he wondered why the dog didn’t slip. Then he looked at Prince’s paws and saw little grooves. At home, Sperry cut a herringbone pattern into a piece of gum rubber and attached it to the bottom of one of his shoes. When warmer weather came, he reportedly had the shoes tested by his deckhand, who poured a bucket of water over the deck of Sperry’s sailing boat, the Sirocco, then ran across the boat without slipping into the Long Island Sound.
When I got to New York for college, I brought my dark suede Top-Siders. As I walked into my first rush party that September, the herringbone rubber stuck to the floor. Unlike the Sirocco, the Delta Sigma Phi house on 113th Street was sticky with Keystone Light. While we played beer pong, older guys stared at my feet. Around me, kids from Exeter and Dalton wore white sneakers. They associated boat shoes less with the Long Island Sound and more with outlet malls in the Sun Belt.
Three years after Paul Sperry patented his sole-making process, his shoes became official footwear for the US Navy. He later sold the brand’s patents to the United States Rubber Company, which also operated ammunition plants as part of the war effort. Sperry rode postwar expansion in the ’50s, the prep boom in the ’80s, and the second prep awakening that came in the aughts, and I got to college around its peak.
In 2012, the year I wore them to rush, Sperry Top-Siders were the crown jewel of Wolverine Worldwide’s $1.24 billion acquisition of Collective Brands’ Performance + Lifestyle Group. By then, though, the boarding school Delta Sigs had changed to streetwear, or even “normcore” clothes from the Great Plains. At the same time, it became generally less cool to dress like you went to Taft. Boat shoe sales dropped year over year, and last year Wolverine offloaded Sperry to the Authentic Brands Group and the Aldo Group for $130 million.
But the tide goes out, the tide comes in. At its spring 2024 show, Miu Miu debuted a bleached leather boat shoe, currently retailing for $1,020. The Row, Jacquemus, Burberry, and Prada came next, and Vogue declared Top-Siders the shoes of summer 2025. Last month, when I was in Berlin for my next book, I wore some G.H. Bass boat shoes in line at Berghain. Unlike my Delta Sig brothers, the bouncer decided they fit in. A while later, he let in a guy in an Augusta National hat.
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