How To Wear Boat Shoes

With summer just around the corner, it seems time to revisit some style rules that everyone should keep in mind for the warmer months. Normally we think these rules are pretty obvious but we have noticed many rule breakers out and about on the streets. (Yes, we have seen them on the streets of northern cities as early as February). As the footwear choice of frat boys, yacht owners, and smug douchebags everywhere, boat shoes used to get a very bad rap. Now worn by every second hipster, these shoes can easily fall from fashionable to fashionable fail. But if worn with subtlety and know-how, they are the classic summer shoes every man needs to own. Here’s how to navigate:

Boat shoes are summer shoes

As noted above, boat shoes are summer shoes. Yes we need to repeat this: summer shoes. So if the weather is cool enough for you to warrant socks with your boat shoes, then it is too early for these nautical inspired footwear. Nothing makes a man more unstylish than being a season jumper; you look daft with socks and deck shoes. No this does not mean you should never wear socks with boats shoes, in fact we recommend always wearing socks to preserve the life of your footwear and keep the odors at bay (add some foot powder for extra measure in the summer months). But boat shoes require those type of socks often referred to as no-show socks; those little socks that resemble ballet slippers more than socks. Yup, they may not seem manly but they are a necessary evil to get this look right ( but here’s a tip: just slip them off and store them in your shoe if ever required to take your shoes off in the company of others).

They go with everything

Some footwear just goes with everything from tailored trousers to denim to shorts – those shoes we call classic sneakers. While others, like boat shoes need to be paired with a bit more care if you want to get it right. If you want to look modern and not like a frat boy, keep boat shoes away from khakis and instead pair them with dark denim or tailored navy blue suit. Keep the look breezy but tailored; we are talking tie-less, open shirt collar and a slim pant leg with that suit.

How to break them in

Proper boat shoes can be a pain to break in; they were designed with tough enough leather to stand up to expeditions at sea, which can sometimes mean a few blisters as you break them in on shore you landlubber. So here’s a trick, get them wet. Yes, this sounds sacrilege in the world of leather shoes. But trust us, getting them wet and wearing them as they dry will allow the leather to shape to your feet providing a custom fit and it softens the leather ever so slightly. Soon enough, you will find them to be your most comfortable summer shoes.

Stick to the classics

When in doubt, stick to the classics. If you feel unsure of how to incorporate boat shoes in to your wardrobe, may we suggest you get yourself a classic looking pair? Many designers have re-imagined the boat shoe over the years but one should always go back to the humble beginnings of this style. These shoes were originally created by Paul Sperry, a sailor, who was intrigued by the ease in which his dog ran across ice. After inspecting his dogs paws he noticed a herringbone-like pattern in the dogs paws helped with traction. This soon lead to a company that has provided the footwear for many of the sailors who have won America’s Cup. If Sperry’s were good enough for them to navigate the sea, they are good enough to help you navigate your sartorial decisions.

Christian Dare

Christian Dare

Christian Dare spent much of his formative years working in the fashion industry as a Visual Manager before pursuing a Masters’ Degree in Design. He is the Principal at Christian Dare Creative, the co-founder of Stylist Box and runs a successful men’s lifestyle blog, Christian Dare Edited,focusing on menswear, interior design and craft cocktails. You can find him online at www.christiandareedited.com or follow him on Twitter @christiandare but he is more fun on Instagram christian_dare. 

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