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It was December 25th, 2004. The family huddled around the roaring fire among a flurry of torn wrapping paper while the smell of maple sausage wafted in from the kitchen; my stomach growling in anticipation of Dad’s famed Christmas Breakfast Sandwiches. With heavy hearts we began to tidy up the festive mess, signifying an end to our Christmas Morning. While collecting the balled up shreds of paper, wrapped thoughtfully around gifts not hours before, I came across a forgotten present tucked behind our Douglas Fir. As I reached behind the branch, a shock of excitement ran through me as I read my name across the top. I tore away the holiday wrapping to reveal a simple blue shoe box. Across the top in white bold letters read “Sperry Top-Sider,” the contents label read “Men, Size: 11, Brown Buck.” Little did I know how much my life would change as I slid the top off the box and revealed my prize.
Back then, I didn’t know much about fashion, but I knew what I liked. Without hesitation, boat shoes became a staple in my wardrobe. In the fall and winter, they paired well with wool socks and jeans. Come spring and summer, they rode shotgun with khaki shorts while the socks stayed home. It was a sure thing, an ace in the hole, they fit any occasion, and looked better the older they wore. I never stressed about my footwear because it was always taken care of.
When my Brown Bucks were ceremoniously retired after years of honorable service, I signed up for another tour. Three more years would follow in my new go-to: Men’s Size 10.5, Authentic Original Two Eye Classic Brown.
These carried on into my years of higher education. Parties, formals, walking to class, late night study sessions in the library, they were there. They were the Swiss Army Knife of footwear. Worn with Chinos and a slick button down, you were ready for any formal occasion. Throw on a pair of jeans and a T-shirt, you just added class to casual. A favorite of mine: gym shorts and long sleeve T-shirt with boats gave the ultimate laid back vibe. No matter what the event was, boat shoes had my back and were there for so many memories. I graduated in boat shoes, and the night I lost my virginity I was wearing boat shoes. The only time I’ve fallen head over heels in love, those heels were clad in premium leather and non-marking soles.
You can see why I hold the topic of boat shoes so close to my heart. I’ve made long-standing friendships based simply on love for these fashion icons. I made enemies as well. A culprit had once insisted in soaking a new pair in salt water to avoid the blisters during the breaking in period. I disagreed. I held the belief that a boat shoe had to be broken in like a wild Mustang. Only through blood, sweat, and dedication could the shoes and their wearer build a true bond.
As I’ve grown older, my fashion senses have changed. My time in boats has declined since I graduated. Working in the real world meant an expendable income and a more professional wardrobe, so I’ve invested in Oxfords and have loved every second of them. Through this time, my worn Sperrys have always been there, usually in summer to step up where all other footwear stumbled.
Now I have to say goodbye. My age has finally caught up to me. Years of running injuries have left me with a recurring case of plantar fasciitis. After putting in 40 hours wearing Oxfords at the office, the thought of sliding into something flat with no support makes me cringe and reach for the Bourbon with an Advil chaser. It’s time to hang them up. Maybe down the line I’ll throw them on to see if I still got it, but the grind of a 365-day grueling schedule? My body just can’t take it..
Image via Shutterstock
Respond
I’ll never hang mine up.
Keep fighting the good fight
That’s much easier for us engineers to say. You could wear boat shoes to the office every day and you’d still be more fashionable than 99% of the guys wearing white socks with dress shoes.
I’m riding Sperrys till I die
Is hanging up the Sperrys like the shoe equivalent of getting a minivan?
Peyton threw 4 interceptions with plantar fasciitis and you can’t even walk your dog in them? Pussy.
This comment is severely underrated.
This is a sad story.
Gold Cups
Like walking in tempurpedics. Now, post grad it isn’t acceptable to wear Top Siders every day for 10 months a year (PGP), I hope these little puppies can last me more than a year without wearing holes through the toe box.
No, I’m not crying. Stop asking.
If y’all can recommend a better alternative to Sperrys then I might retire mine. But, until then, what am I supposed to wear?
I love my Sperrys, but I recently found myself wanting something just a tad more refined. That is when I discovered the bit driver moc. I like the Onward Reserve brand in brown but Rowdy Gentleman has a good selection.
Welp. That basically ruined my day.
Reading the comments I’ve learned flip flops and shorts aren’t a thing outside of Florida
They absolutely are on the west coast. As long as they’re Reef or Rainbow, and that itself turns into a debate.
But like, what age you going to wear with shorts? Sneakers?
Driving mocs or casual loafers are the grown up boat shoe
Agreed but they do get hot and sticky in the summer
Heard Man Outfitters has some great casual sneakers.
Smooth plug there..
I’ve been playing around with the casual New Balance looks, although not terrible it’s just not the same.
Dad?
I’m currently in crisis mode, wearing jeans as long as I can to delay the inevitable fact that I need a replacement. Probably going to go with a low profile sneaker though.