Why the Sperry Top-Sider is the Most Versatile Shoe Known to Man
- Business Bill
- Jul 13, 2017
- 6 min read

As a man with very little time on my hands, I find that the less time I can spend on any one task, the more time I can spend doing other things like having a cold one with the boys. This is just one of the many benefits of purchasing a pair of Sperry Top-Siders. Because I own a pair of Top-Siders, I spend less time looking for new and varying styles of shoes when I’ve gotten every last step out of the beautiful foot protector before it and when deciding what shoes to wear each day. All this time added up over a lifetime results in at least 3 to 4 trips to the links, rippin’ darts in the general direction of the pin and likely having a few cold ones with the boys. Other reasons include spending less of my hard-earned cash on different types of shoes, allowing me to afford more cold ones to enjoy with the boys. And the best reason of all is that you just look fly wherever you and the boys happen to be having those cold ones, whether that be the local bar, your yacht or maybe just the back porch of your mansion. Now just in terms of the increase in cold ones you could have, it should be apparent why having a versatile shoe is extremely beneficial to both the emotional and physical health of the Sperry owner. However I've yet to have proven the versatility of the Top-Sider thus far. I don't believe in fake news and will not be accused of deceiving the great readers of this publication and therefore will propose to you some of the many occasions where you can wear your Top-Siders, as well as the few occasions during which they are not appropriate, after which I would challenge you to present to me a more versatile footwear solution.
Where You Should Wear Your
Sperry Top-Siders
On a Boat
The Occasion for which the Top-Sider was Designed
When the forefathers of Sperry were sitting together drinking thousand year old scotch by the fireplace and finalizing their plan to instruct FDR how to fix the stock market crash of the 1920s, which would later become the New Deal, they realized that a new style of shoe was needed in America. Next they created their ideal shoe, envisioning the generations to come wearing these handsome shoes atop the decks of their sailing vessels. Whether you're on a yacht or a simple pontoon boat, the Sperry is intended to be paired with your casual boat wear. Whether that be a swimsuit and tank top, or a pair of khaki shorts and your finest Hawaiian shirt (Hawaiiantology by Big Tony), Sperrys look good with whatever you're wearing on that big beautiful boat of yours. The only time you should not be wearing your Sperrys on a boat is during a corporate or formal event during which your dress shoes are obviously required unless you’re hoping to be sent overboard for the entertainment of other guests.
The Bar
Whilst Presumably Having a Cold One, Likely with the Boys
The bar will quickly become a regular location to find the young adult immediately after they reach their 21st birthday or in some cases beforehand. It is the fraternity house of the adult world, but with fewer restrictions to entry, yet less fun to be had once inside. However for adults like myself, it's all we have left now. This means you should look your best here at all times and that’s where your Sperrys come in handy if you want to catch the attention of that hot bartender who just served the 17 people directly to your left and right before you. Although some say that Sperrys should not be worn with long pants, after careful and systematic research, I've been able to unequivocally deduce that this is simply not true, some might even say, “donkey-brained”. However, just to be sure, it is ideal to wear colorful and/or patterned casual socks as a slight barrier between your sexy feet and those glorious kicks you have on.
In Class
The Breeding Ground for America's Next Great World Leaders
For those of you still lucky enough to call yourselves college students, class is a perfect place to be wearing your Sperrys. You can wear them with anything other than sweats, but you just shouldn't wear sweats to class anyways you fucking scrub. Wearing your crispest pair of Sperrys with khakis and a button up are the look that will impress both your professors, and the babe of that sits on the other side of the room that denied your invitation to the school-approved "nature hoes and recycling bros" party, that your fraternity threw last wednesday. The college classroom is the place where you can wear just about anything and truth be told, the Top-Sider is the shoe that can be worn with anything casual. So rather than continue to list occasions your Sperrys should be worn, I'll simply tell you the two places you should leave the Sperrys at home and opt for a different foot glove.
Where You Should NOT Wear Your
Sperry Top-Siders

At Work Grinding for the Future Wife and Kids
Or Any other Formal Occasion
This one should be obvious but there are still people out in the world wearing cargos so I guess it should be addressed. The picture above shows four millennials wearing what is described as semi-formal and although you cannot see their faces due to crop, I can assure you they do not fuck. To make matters worse, three of them are not wearing socks, which is not allowable in the dress code of any adult occupation out there. If you work in an office, wear at least a dress shirt and tie if not a suit, or wear a some loafers with your khakis if you’re hoping to never get promoted. However, I have not forgotten about the blue-collar man who works harder than us others and gets generally less to show for it. If you are this hard-working American, you likely should not wear Sperrys to your job for both safety reasons and so that you can keep them clean for when you meet the boys at the bar for a cold one after a long day of being the backbone of this country. For those of you in the pseudo-corporate world working for a tech start-up or something else where they don’t give a shit what you wear, congratulations, you can wear Sperrys to work too but please buy some dress shoes too just in case you ever get invited to a wedding.
The Gym
Or other Physical Activities
Obviously you don’t want to be that douchebag in his Sperrys and polo shirt over in the corner using the machine the wrong way because you saw it on a fitness video from a Buzzfeed list. (Buzzfeed is fake news). There’s just no reason to have Sperrys on in the gym and if you’ve done it before, know that everyone there thinks you’re a tool. In fact any physical activity or sport should be performed in something other than a pair of Sperrys. Even the 12 year-old from down the block could cross you up like a Bavarian pretzel and drop a saucy lay-up into the 7 ½ foot rim in his driveway if you don’t have the proper athletic base from at least a tennis shoe. Golf being the extension of the office that it is will never allow for a pair of beautiful Sperrys to be worn for any reason other than if you work in the clubhouse and had to take over because the cart girl quit due to your “constant staring”; don’t be that guy. Other than a game of cornhole in the backyard at the grad party you’re crashing or when playing a game of catch with the accident of a kid you named Chucky, Sperrys should stay in your closet while you pretend to lose at racketball to your 57-year old boss.
The Bottom Line
The Sperry Top-Sider can satisfy your need to house your feet under, not in every circumstance, but in more than any other shoe available today. In fact any occasion in between the going to the gym and the ever glorious casual fridays at work can feature you looking dapper in a pair of Sperrys. The crisp Nike tennis shoes you used earlier while making gains in the gym, cannot be paired with your khakis on your way to the bar. And your dress shoes cannot be worn with anything less than a pair of slacks without running the risk of being stopped on the street by do-gooders asking what has happened to you and how they can help. There simply is no shoe on the market today as versatile as the Sperry Top-Sider. However, if any of the studs that make up the Greener’s World audience would beg to differ, I’d be happy to hear you out and subsequently tell you why you’re wrong. If you’d like to know where you could find yourself a good deal on some magnificent Sperrys, figure it out yourself you can use Google.
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