Okay, but can we talk about that super awkward moment when you realize that most guys don’t really know how to dress for fraternity rush? I was totally in the dark too! While sorority recruitment is all about mood boards and glam ‘get ready with me’ videos, fraternity hopefuls are often left to fend for themselves—unless mom swoops in with a trendy outfit for the end of summer. What does that mean for us? Well, a lot of us just showed up in our high school party clothes. Picture me trying to make an impression in boat shoes at my first fraternity party. Not exactly the power move I had in mind! 😅
The Boat Shoe Era: A High School Staple
Back in my all-boys school days in Dallas, we practically lived in our Top-Siders. Seriously, these shoes were like a rite of passage. From fifth grade on, we dressed like we were gunning for Ivy League colleges. Our uniforms got a little upgrade with Harvard, Yale, and Princeton sweatshirts, Vineyard Vines belts, and of course, those classic Sperrys. Everyone had that perfect tan leather pair, all broken in like a favorite baseball glove. At lunch, you’d find us playing lacrosse at half speed, trying to keep our feet (and those mid-calf socks) snug in our shoes. Who else remembers that vibe? 🙋♀️
But here’s a fun fact: the history of the Top-Sider is even more elite than I ever realized. Paul Sperry, the genius behind the shoe, had quite the background—growing up in Connecticut and attending prestigious schools like Taft and Dartmouth. One chilly day in the 1930s, he watched his cocker spaniel, Prince, effortlessly run across icy ground and wondered why his dog wasn’t slipping. After some experimentation, he created a herringbone pattern on gum rubber, and voilà—Top-Siders were born! Can you believe that? They were even tested on his sailing boat, the Sirocco, proving their grip on slippery surfaces! 🚤
From College Rush to Cultural Shift
Fast forward to my college days in New York; I was still rocking my dark suede Top-Siders. Walking into my first rush party that September felt like déjà vu—and a sticky floor, thanks to all the spilled Keystone Light around me. While I was trying to blend in, other guys from Exeter and Dalton were flaunting their white sneakers, clearly associating boat shoes more with outlet malls than sailing on the Long Island Sound. Major style clash, right? 🤦♀️
Here’s where the plot thickens. Just three years after Sperry patented his design, his shoes became the official footwear for the US Navy! He later sold the brand’s patents to the United States Rubber Company, who jumped on the post-war expansion wave. The ’50s brought a prep explosion, the ’80s saw a revival, and by the time I hit college, it was at its peak. But things took a turn.
By 2012, when I wore those Top-Siders to rush, they were part of a massive acquisition deal worth $1.24 billion. But oh boy, how fast trends can change! The boarding school vibe was shifting towards streetwear and normcore styles, and suddenly, dressing like you just stepped out of a prep school wasn’t the look anymore. Boat shoe sales started to decline, and eventually, the brand was sold for a fraction of its worth. Can you imagine? 😱
The Comeback: Fashion’s Circular Nature
But just like the tide, fashion has its ebbs and flows. At the recent spring 2024 show, Miu Miu showcased a bleached leather boat shoe with a jaw-dropping price tag of $1,020! Can you even? Other big names like The Row, Jacquemus, Burberry, and Prada followed suit, with Vogue declaring Top-Siders the shoes of summer 2025. Talk about a comeback! 🔥
Last month, while I was in Berlin for my next book, I decided to wear my G.H. Bass boat shoes while waiting in line at Berghain. And guess what? The bouncer actually let me in! It felt like a little win for the boat shoe army. Who knew these shoes would have such a wild journey from fraternity parties to high-fashion runways? It’s proof that sometimes, what goes out of style can come back around in the most unexpected ways. 💫
