To Boat Shoe or Not to Boat Shoe: Sole Searching for Summer Footwear
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Unless you’re Simon Le Bon in Duran Duran’s “Rio” video, a tourist in Toto’s “Africa,” a dad with a quarter-keg dad bod and beloved collection of faded Margaritaville t-shirts in the closet, or an East Coast prep school student whose only idea of a fashion accessory is a Lacrosse stick, are boat shoes acceptable footwear in the summer?

The boat shoe has baggage. The chillaxed shoe with the herringbone pattern of grooves on its sole is either revered like a Brett Easton Ellis novel or… well, loathed like a Brett Easton Ellis novel. Both the shoe and the novelist are inextricably tied to the 80’s, and it can be argued that Patrick Bateman, the Wall Street serial killer in “American Psycho,” is really just an example of the 80’s preppy lifestyle run amok.

But the problem with the boat shoe runs deeper than its image as a 80’s fashion trend. According to Tom Chamberlain, editor of Rake, “The boat shoe/docksider/deck shoe, is, forgive the pun, adrift in men’s shoe trends.” In other words, the boat shoe has an existential problem, Hamlet-esque in proportion and as equally as ponderous as the Prince’s soliloquies.

The boat shoe has an existential problem, Hamlet-esque in proportion and as equally as ponderous as the Prince’s soliloquies.

Here are just a few of the questions the modern boat shoe-wearer is confronted with:

Is it acceptable to wear boat shoes with socks? (Never.)

Is foot fungus on the rise because young men are wearing boat shoes without socks? (It’s an urban legend, readers.)

Do a pair of Sperry Topsiders go with jeans? Of course, especially if you’re going for that debauched, Blaine (“Blaine? His name is Blaine”) look in “Sixteen Candles,” or you want to rebrand your skinny jeans, early aughts, Strokes style.

Sperry Top Siders, the original American brand of boat shoe designed in 1935 by Paul A. Sperry.

Is an Oxford shirt and blue blazer an official part of the boat shoe ensemble? (Only if you believe the preppies who wrote The Preppy Handbook.)

Do you need to own a 20-foot Boston Whaler and a pair of Nantucket Reds in order to wear boat shoes? (It helps, yes… and a second home on Martha’s Vineyard seals the deal, not to mention a timeshare in St. Maarten.)

The dos and don’ts of wearing boat shoes are varied and many, and instead of trying to figure what’s acceptable or not, it’s easier for many men to reach for a pair of sneakers or sandals in the summertime.

Tom Chamberlain goes on to say, “Most footwear, from espadrilles to boots, has gone through some sort of renaissance over the past five years. Boat shoes, however, have never been reinvented, upgraded or injected with any sort of street cred.”

Most footwear ... has gone through some sort of renaissance over the past five years. Boat shoes, however, have never been reinvented, upgraded or injected with any sort of street cred.

Of course, the first thing one should ask Mr. Chamberlain is why the boat shoe needs street cred. It’s a boat shoe, after all. You’re not going to go skateboarding in a pair of Sebago’s or Topman’s. The boat shoe needs ocean cred, and when it’s on land, it needs beach cred… or at least beach bar cred.

Second, the boat shoe has gone through several reinventions in its 83 year history. Paul Sperry invented the boat shoe in 1935. After watching his dog, Prince, run across a pond during a snowy Connecticut winter, Mr. Sperry decided to try to create a shoe with a non-skid sole. The classic boat shoe’s herringbone sole is said to have inspired by the grooves and cracks on his dog’s feet. In 1939, Sperry’s became the official shoe of the U.S. Navy. Due to the high cost of leather during World War II, Sperry sneakers and boat shoes skyrocketed in popularity, and by the 1960’s, their reputation as an All American brand was solidified by the Kennedy family. Sperry’s have served as the official footwear of the America’s Cup as well as the U.S. Olympic sailing team.

Youth World Sailing Championship 2017, Sanya, China. Photo by Jesus Renedo / Sailing Energy / World Sailing

Part of the beauty of the boat shoe is its versatility. From the yacht to the catamaran to the Tiki bar to the tennis club, the casual, dress down shoe is tailor made for the carefree days of summer. You can wear it to the office, the Friday night office party, the beachside bar and the Michelin star restaurant, and this simple, no fuss approach to fashion is what many men are looking for in the summer. It’s bad enough that men have to worry about shorts, a notoriously difficult piece of clothing to wear with styles that range from camp counselor chic to cargo grunge. Some men look good in shorts; most don’t. The last thing we need to worry about is what we’re putting on the end of our legs.

So, to boat shoe or not to boat shoe… that is the question this summer. Honestly, guys, does Rio dance on the sand?

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