Out to Sea: 20 Best Boat Shoes for Men

Apr 23, 2015

Category: Style

Nothing screams “summer”—or “long weekend”—like a pair of boat shoes. With a lineage tracing back to 1930s Connecticut (you surprised?), these shoes are classic enough to take you from a morning sail and accompanying day on the beach to a nice dinner at a waterfront restaurant, or Friday morning in the office to your beachside summer rental. Read: come summertime, they’re the most versatile shoes in your closet.

So whether you’re on a boat, on a beach, or sitting in your office staring at a photo of an ocean on your desktop and praying for Friday to arrive, these are the shoes you should be wearing this summer. And bonus—wearing boat shoes means that you can give your beloved statement socks a rest—and after this winter, they need it.

Lands End Mainstay

Lands’ End Mainstay Boat Shoes

You can get the classic look without the high price tag with these Mainstay Boat Shoes from Lands’ End. The olive and navy combination can be worn to a casual Yacht Club dinner or a beach BBQ. [Purchase: $50]

Red Tape Boat Shoes

Red Tape Boat Shoes

It might seem blasphemous to wear a European-designed version of an American classic, but we can make an exception for these boat shoes from Red Tape. They maintain the same basic style of classic boat shoes, with modern twists, like streamlined laces. Bonus: the buttery leather will make it look like you paid way more than $63 for these. [Purchase: $63]

Sperry Authentic Original Flag Day 2-Eye Boat Shoe

Sperry Top-Sider Authentic Original Flag Day 2-Eye

Sperry specializes in classic boat shoes, but its Flag Day series gets a bit more playful—offering up shoes in color combinations inspired by flags from countries across the globe. These green, blue, and yellow shoes (likely inspired by Brazil) will definitely make a statement when you’re out at sea. [Purchase: 65]

Sperry Authentic Original Cyclone Leather 2-Eye

Sperry Top-Sider Authentic Original Cyclone Leather 2-Eye

Boat shoe aficionados will tell you that Sperry is the grand daddy of them all—they were the original maker of boat shoes in the 1930s, and since then, they’ve been the standard-barer for creating awesome boat shoes that are always affordable. The Authentic Original is the first shoe offered by Sperry Top-Sider in 1935, carrying a classic look that will look good with anything from chinos to your favorite pair of worn-in shorts. Available in a veritable rainbow of color combinations, we bet you can’t buy just one pair. [Purchase: $75]

Sebago Docksides Neoprene

Sebago Dockside Neoprene

Founded in the 1940s and named after a town in Maine (the coastal state that embodies the nautical lifestyle), Sebago Docksides had a moment in the 80s when they were the footwear dujour for preppy college kids and for the US Sailing Team. Even though they’re 30+ years away from their heyday, Sebago Docksides still look damn good, and this sleek cherry red model is one of the best. [Purchase: $80]

Hampton Two-Toned Boater

Hampton Two-Toned Boaters

GH Bass & Co. is another historic company with roots in coastal Maine, and while they’re famous for their penny loafers that debuted in the 1930s, their boat shoes are stylish, solid, and will last you the entire summer—and then some. [Purchase: $88]

Topman Navy Leather Boat Shoes

TopMan Navy Boat Shoes

There’s no color combination more classic than navy, brown, and red, and these shoes from TopMan have them all. The dark navy leather shoes feature white stitching, oxblood red laces, and a durable brown sole, meaning they can go anywhere—from your office to the train to whatever seaside weekend plans that await you. [Purchase: $90]

Sebago Docksides

Sebago Docksides

There’s something about clothing that looks and feels worn-in, which is why the fashion industry made a killing selling those broken-in, faded jeans and super soft t-shirts. Same thing applies to boat shoes—each time you wear them on a nautical jaunt, the leather stretches and develops a patina that makes it look like you’re the type of guy that spends way more time on the ocean than you actually do. That’s why it couldn’t hurt to start the season off with a pair of pre-faded Sebago Docksides that already look like they have a summer’s worth of stories to tell. [Purchase: $100]

Band of Outsiders for Sperry Topsider AO Stripe

Band of Outsiders For Sperry Top-Sider Striped Boat Shoes

Hip fashion brand Band of Outsiders has teamed up with Sperry Top-Sider to bring a little rock n’ roll to your WASPy yacht club. This pair has the build of a classic Sperry, but is made out of canvas instead of leather and features a black and white striped pattern that will look just as good on city streets as they do on the docks. [Purchase: $125]

Sperry Python Boat Shoes

Sperry Top-Sider Python Boat Shoes

By the time summer gets into full swing, you might start to feel like everyone has a pair of boat shoes on. Want to stand out from the country club crowd? Pick up a pair of these Python boat shoes from Sperry. The [faux] python texture jazzes up the classic boat shoe look, making them just a touch dressier than regular leather pairs. [Purchase: $128]

Sperry Top Sider Gold Cup Perforated Leather

Sperry Top-Sider Gold Cup Perforated Boat Shoes

If you have a closet full of Sperrys and want something a bit different, consider upgrading to the brand’s Gold Cup Collection. The Gold Cup shoe’s claim to fame is its meticulously perforated leather sides, which allow for ventilation, and anyone who has taken a whiff of your shoes after a particularly active summer day will appreciate the upgrade just as much as you will. [Purchase: $150]

Ralph Lauren Barnard

Ralph Lauren Barnard Boat Shoe

Ralph Lauren—yes, the same Ralph Lauren who makes the indestructible oxford shirts you’ve had in your closet since high school—might not be known for its footwear, but they make some gorgeous boat shoes in colors that will ensure you’ll get noticed this summer. And if you’re the type of guy who can pull off turquoise or orange deck shoes, you’re the type of guy we want to hang out with. [Purchase: $165]

Paul Smith Dagama

Paul Smith Jeans Dagama Boat Shoes

Half boat shoe, half chukka boot, these handsome leather lace-ups by popular British designer Paul Smith allow you to add a little formality to an otherwise casual shoe. Is your friend getting married at a marina this summer? These would look great with a tan suit, and you’ll be able to cut up the dance floor more easily than the rest of the guys sporting their uncomfortable dress shoes. [Purchase: $197]

Quoddy Canoe Shoe

Quoddy Canoe Shoes

At Quoddy—a shoemaker named for the small town of Passamaquoddy, Maine where it was founded—they take the term “handmade” very seriously. Their website features photos of older gentlemen showing off the calluses on their hands they got from making shoes. They are not playing around. A pair of their classic canoe shoes might be a bit pricey, but trust us—this is as close to getting a pair of shoes crafted by old-timey cobbler as you’re going to get. [Purchase: $275]

Quoddy Classic Boat Shoe

Quoddy Classic Boat Shoes

Shoe obsessives rejoice—because of the extremely handcrafted nature of Quoddy’s shoes, you’re in the driver’s seat when browsing their wares. Start with the classic boat shoe design and you can choose the color of the leather, sole, laces, lining—even the stitching. It doesn’t get more custom than that. [Purchase: $295]

Rancourt and Co For Brooks Brothers Waxed Canvas

Rancourt & Co. Waxed Canvas For Brooks Brothers

You have a bunch of boat shoes that have seen their share of sea, sun, and sand, but you’re looking to add a nicer pair to your collection—one that you don’t want to get wet. Look no further than this pair from Rancourt & Co, made exclusively for Brooks Brothers. Available in olive or navy and crafted with meticulous attention to detail, these are worth investing in. A word of caution, though—people are going to see you sporting these shoes and assume you’re picking up the check. [Purchase: $328]

Eastland Yarmouth USA Canvas Slip On

Eastland Yarmouth USA Slip-Ons

Another Maine-based company lending its expertise to the boat shoe world is Eastland, a brand that has been producing quality kicks since 1955. These Yarmouth Slip-Ons (named for Yarmouth, Maine, of course) are made out of Gridwax Army duck canvas, which gives them a unique look and makes them virtually indestructible. [Purchase: $330]

Mark McNair Grey Suede

Mark McNairy Grey Suede Boat Shoe

British designer Mark McNairy’s take on a classic boat shoe is an impressive feat—this pair in grey suede will look unique but unpretentious wherever your summer takes you. [Purchase: $375]

Bally Gabel Boat Shoe

Bally Gabel Boat Shoes

Founded in the 1800s in Switzerland, Bally has been creating quality shoes for nearly 200 years. That should be reason enough for you to plunk down $500 on these beautifully-made navy and red Gabels. They’ll last you almost as long as the company’s been around. [Purchase: $495]

Brioni Suede Boat Shoes

Brioni Suede Boat Shoes

Why buy a boat when you can buy a pair of boat shoes? Sure, these are a splurge, but these handsome suede shoes made by the legendary Italian fashion house are worth it. Brioni boasts quite an impressive list of devotees—Clark Gable, Cary Grant, Al Pacino, and John Wayne just to name a few. Convinced? Good—just remember: suede and water don’t mix well. [Purchase: $710]

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