Tom Conroy
Audio By Carbonatix
Just in the last couple months, I’ve seen fashion trendsetters from Vogue to GQ proclaim from up on high that the humble boat shoe is officially back in the cultural zeitgeist. The TikTok girlies are abuzz and snatching up pairs from the top footwear brands.
And yet here I sit, a native East Coaster who’s been wearing Sperrys since I was a toddler, wondering how the most well-worn pair of shoes in my closet went from the mark of an old fogey to something coveted by zoomers without me even noticing either trend shift.
If you’re asking my opinion on how this happened, there are two simple truths:
- Preppy never goes out of style.
- With enough time, something that’s popular will usually become unpopular and eventually become popular again.
I don’t need some influencer to tell me that my Sperrys are great. I’ve known that all my life. I’ve had my current pair for at least five years. Like a fine bottle of wine, these shoes only get better with age.
It went without saying that every time I had to look nice during the summer as a kid, I threw on a pair of Sperrys. When I attended an all-boys Catholic high school, the dress code required nice black or brown shoes. Thankfully, Sperrys fell into that category. Regrettably, I did have to wear them with dress socks, but it was worth it. That would be the last time I would break that cardinal rule.
When I moved to the Midwest to attend college, I was surprised by the cultural shift around people wearing boat shoes. No longer was it a nonchalant fashion decision. It was a statement made to show how preppy you were (especially among frat boys). Seemed strange to me because I wasn’t in a frat, and I wasn’t trying to flex my preppy street cred. I just wanted to be comfortable and they went with most of my wardrobe.
Years went by. Shoes came and went out of my closet, but my Sperrys were always the constant (albeit an updated pair every few years when they reached the end of their lifespan). I’m a married man in my 30s, and a lot has changed in my life, but the love of my Sperrys has never dissipated.
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For those of you youngsters throwing on a pair of boat shoes for the first time this summer, welcome. Nothing beats the feeling of wearing a pair of shoes that is equally classy and perfectly acceptable to wear without socks. And yes, the latter is NON-NEGOTIABLE.