Nothing Say Leisure Like Boat Shoes

Boat Shoes, the gentlemens ledger

Every change of season presents an opportunity for a transition in your personal style and with Spring in full swing, now is the time to do just that. New clothes hit the rack, new trends emerge but the best part is pulling out the pieces that you could not wear all winter long. So today, I urge you to slap those boots out of the way, go in the back of that closet, and grab those boat shoes that have been patiently awaiting your return all winter long.

The boat shoe, also known as deck shoe or top-sider was born as part of the work wear for sailors. These shoes as we know them to be today were invented in 1935 by Paul A. Sperry of New Haven, Connecticut after observing his dog’s ability to run easily over ice without slipping. As an avid sailor, Sperry was faced with the problem of dealing with a slipper deck without any shoes that provided traction, so he decided to cut slits in the soles of his shoes to mirror the grooves and cracks of his dog’s feet to recreate the same traction.

Today, boat shoes are the footwear that epitomizes sailing, summer and leisure. This is the footgear that will bring forth memories of vacations past, relaxing days on a beach perhaps, away from the stress of everyday life and a time when you felt as though your life’s purpose was to be at ease and just enjoy the present moment.

Although we can’t all live in this bubble forever, we can bring a little piece of it with us in our everyday life this Spring and Summer by added a pair of boat shoes into our everyday gear.

Boat Shoe Styles


This summer staple isn’t only reserved for Nantucket or daddy’s yacht (for the lucky few), these shoes can be worn in the same manner that you would a pair of loafer or sleek sneakers. The classic look of course would be to pair your boat shoes with any color of chinos and a polo but you have a much larger range of options at your disposal. Try pairing these nautical kicks with a pair of slim fit shorts, a dress shirt with the sleeves rolled up and a pair of aviator sunglasses like the picture to the far left up above for a weekend casual look.

Don’t be hell bent on chinos alone, these shoes of the sea also pair really well with other warm weather pants such as linen and some people like to wear them with jeans. Jeans are a good pair but personally, I like to pair my boat shoes with lighter colored pants which gives off more of a European swagger.

As you will notice in the photos above, deck shoes come in a variety of designs, materials and colors. In addition to the classic leather style, you can also find twill and suede and it’s only a matter of time before a new fabric is used. For all I know, it may be out there already but I’ll let you take on that Google search for yourself and you can let me know about your findings.

What I would absolutely not do is wear these shoes with socks! There has been a long debate about whether or not socks can be worn with boat shoes but in my strong opinion, I think that they do not.

Any time I have seen a man wear socks with his boat shoes, the combo looked as dorky as wearing socks with sandals and if your on this site, I trust that you already know how unethical that combo is in the laws of style.

The Sock-less Shoes Experiment


Visually, and bare with me here, I think socks with boat shoes tend to look a bit dorky because of the shapes of boat shoes. Unlike most fashion forward men’s shoes today, boat shoes have more of a round shape rather than the elegant elongated look that has become the new norm.

With that in mind I invite you to test my theory. Try on three different pairs of any shoes that have an elongated shape and are free of shoelace (such as loafers or monk straps) and three that have a rounded shape that are also void of laces. Try them all first with socks and then without and see if you notice my point of view. If you disagree, let me know and I’ll hear you out (and tell you that you’re are completely wrong).

To be fair, there are always ways to pull off something previously considered a “no no” so unless you are confident you can make socks with boat shoes look suave, I would go sock-less. However, what I would recommend if you want the support of socks without ruining the bare ankle look is to wear these shoes with a pair of no show socks.

Break from the Conventional


Kanye West, suit and boat shoes, the gentlemens ledger

Causal is the name of the game when it comes to boat shoes but you of course decide what casual means to you, style is about SELF expression afterall. Take this photo of Kanye West for instance, the old rule of thumb is to never pair boat shoes with a suit but look how cool he makes it look. My take is, if your going to break the rules, don’t just break them, kick their ass!

The reason this look works is due to the suit in question that the style icon is wearing. This isn’t your pinstriped, power suit or a sleek shark-skin number, this is sumer greatest fabric, linen. Linen is a casual fabric that adds a laid back feel to any item it encompasses. To add, the backpack and suspenders that matches the color of the shoes gives the look a fresh and fashion forward appeal with the addition to the glasses. I think a proper name for this look would be “The Nifty Nerd!”

If you are going to attempt this style stunt, I would take it from the style maverick himself and make sure the suit looks as casual as can be. I would choose a summer suit staple like seersucker, linen or cotton in a deconstructed cut, (ummm, I’m thinking khaki)!!!

The Takeaway


 These ensembles are great examples of how diverse your options are in effortlessly pairing boat shoes to your wardrobe this spring and Summer and bring a piece of summer vacation with you in your everyday life. Now you see how easy it is to dress this maritime footwear with a diverse range of looks from dressing them down with a pair of chinos, to dressing them up with a suit and everything in between. So if you don’t have any of these style wonders in your wardrobe as of yet, click the link here and check out a huge range of different options, happy shopping!

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