Boat Shoes and the Joy of Missing Out on Trends

I'm not going back to the fraternity house.

I’ve owned two pairs of Sperry’s in my life - both in different shades of brown, a light khaki in suede, and a mocha leather pair - that I beat the shit out of. Looking back on it, I purchased my first pair of boat shoes during my senior year of high school. I was in a period of discovering my style, and I was attracted to the preppy look. I knew I was going to an elitist, preppy West Coast college, so I viewed the boat shoes as an investment.

I don’t come from a traditional “prep” background. I’m of mixed race, for starters. I also went to an urban all-boys catholic school in a diverse neighborhood. I’m very fortunate, but I don’t have a trust fund. I don’t fit the traditional mold for a prep. Trust me, I’ve read The Preppy Handbook, and have very little in common with those people.

For the next four years, however; I wore my Sperry Top-Siders in grungy fraternity house basements drinking cheap beer and staying up to the crack of dawn. I’m lucky enough to say that 8 years after college graduation, I’m still friends with some of the people I met in those fraternity houses. Still, I look back at old photos of my outfits - most of which contained the Sperry Top-Siders - and cringe at my choices. I wore them with jeans, chinos, and shorts. I even did the cursed-style move of wearing them with Nike socks and basketball shorts. My dreaded Sperrys went to the end of the world and back with me during those college years.

At a certain point during my senior year, I started to change my style from prep to streetwear. I was starting to rediscover brands like Supreme and Bape, two brands that I had admired from afar, but could not afford. Kanye, Bieber, and countless other celebrities were wearing ripped jeans, flannel shirts, bomber jackets, and Vans. I purchased some light-wash ripped jeans from H&M, a pair of white Vans, and a couple of flannel shirts and overnight, I was starting to feel more like myself.

When the time came to graduate and leave that magical, but overtly preppy, school, I metaphorically left my boat shoes there with that version of me that dressed in khaki pants and salmon Ralph Lauren oxford shirts. It was a version I was happy to leave behind because I never really felt like myself. I grew up in a very diverse neighborhood in San Francisco. I went to “white” schools and I went to more diverse schools. I got the whole experience, but I am not a “prep” by any means. My family didn’t spend summers in the country and winters in ski lodges. We never belonged to country clubs or went to debutante balls. I spent my summers playing basketball with other kids of color who lived in neighborhoods like mine. I have friends who grew up with money and others who grew up with nothing. I happened to go to a university where everyone came from a very homogenous background and I dressed in a way to fit in, and I’m not proud of it.

Those Sperrys were tossed in the trash right when I graduated college before I even moved out of my off-campus house. I didn’t need them where I was going - back to the city that raised me. The point is that I do not come from a preppy background and I regret dressing preppy at one point in my life.

8 years after my college graduation, the boat shoe appears to be rearing its ugly head again. Respectfully, I refuse to partake this time. We all know that influencer and tastemaker culture is to use the current trends at the present moment to beat the crowd to the next great trend. Sneakers have been the footwear of choice for the everyman for as long as we can all remember. In the last 5 years; however, we’ve seen other footwear options come to the forefront of the collective stylish consciousness. Penny loafers became a mainstay in the culture around 2018-2019. Men’s style enthusiasts began ditching their Jordan 1s in favor of Bass Weejuns. Aimé Leon Dore, the cult brand from Queens, NYC created their two-tone leather loafers and suede country loafers, further pushing the notion that loafers were here to stay.

A few years later on, fashion is seeking the next big thing. Of course, sneakers are always going to be the baseline for casual men’s footwear, but loafers have become a step up. Throw in a clog here and there, and you have the basic footwear rotation of the average fashion enthusiast. Somehow, the next footwear style in the pipeline was the boat shoe. Boat shoes were first created in 1935 by Paul A. Sperry as a solution for wearing shoes on a boat without slipping. The shoes are characterized by a canvas or leather body sitting atop a rubber sole and a single shoelace wrapped through the side of the shoe. Since boating is an elitist activity, boat shoes, though very affordable, became a status symbol.

There have been various iterations of the boat shoe outside of the Sperry Top-Sider. The most noticeable one for me is the Timberland Three Eye Lug (pictured below), which features the typical body of a classic boatshoe, but with a thick, rugged sole, mainly for colder months. This variation of the boat shoe is edgier, like you could see them in the crowd of a hardcore show or at an art gallery versus the depths of a fraternity house. I purchased the Supreme collaboration two years ago with the woven leather body, and they’re my favorite non-sneaker shoes that I own.

Now I will never go back to boat shoes because they represent a culture that I am not a part of. Prep is all fine and dandy if you’re just looking at the clothes, but if you take a step back, you’ll realize prep is built on homogeneity. It’s built on being of a certain race and coming from a certain socioeconomic background. Preppy clothing is a means of signaling to the world that you come from a specific club, one that recognizes outsiders and tells them “You are not like us.” It’s a community built on exclusion, meant to further the few members of the club while keeping everyone else down and out.

I’m not joining the trend, and it feels liberating. We as fashion people feel like we get left in the dust when the culture moves at breakneck speed and the items we purchase that are now starting to feel like a second skin become obsolete. I’m still going to wear penny loafers. I still wear a lot of Supreme. Shit, I have some ALD pieces I wear day-in and day-out.

You don’t have to follow every trend, especially if they don’t speak to you. That’s why so many of us preach personal style. Find what works for you, and ignore all of the extra noise. I am not from a place where preppy clothing is the norm, and neither do I fit the preppy stereotype, so I am going to skip the boat shoe trend. Remember the massive, ugly sneaker trend a few years back where people were rushing to Balenciaga to blow $900 on the Triple S. Those are unwearable right now.

I try to participate in trends that I can see transcending the concept of a trend and becoming more of a mainstay in the sartorial landscape. I also try to only participate in trends that speak to me. Prep does not. Ultra-baggy jeans do not. Ugly shoes do not. Sweater vests were not for me and now that trend seems to have passed. Some trends are great, though. Moving away from thinner pants silhouettes to embrace straight and relaxed-fit pants was a great move. The merch era was great. Sambas? Yes, please. New Balances? Even better.

Trends are temporary, but they always come back. It’s up to the consumer to ultimately decide what trends they participate in. Think about your personal style, your interests, etc..when deciding whether or not you want to participate in a specific trend. You never know, it may not be for you, and you‘ll rejoice to know you don’t have to spend money to impress strangers on the internet!

Peace and Love