Tested: The Best Men’s Boat Shoes for Nautical Style

It was only a decade-or-two-ago that boat shoes were primarily associated with a certain breed of preppy, fratty, New Englanders, though both the space and those who wear them has radically changed in recent years. Once again appearing on the runway shoes of reputable labels, slip-on-style top-siders have become increasingly in-vogue and are increasingly being adopted by those looking to pull off a casual yet elegant look. The revitalized interest in this space also makes now the perfect time for us to revisit the top-sider segment for this hands-on review of the best men’s boat shoes. 

Selection & Testing

There are tons of pairs of boat shoes on the market, so in order to uncover the very best, we kicked off our search by focusing on overall style, material selection, and price and value. Using these criteria, we then generated a shortlist of boat shoes that we then got our hands on in order to put to the test. From there, each pair was worn for over a month, allowing them to be broken in. 

This test also saw us scrutinize each pair’s build quality, comfort, both before and after being broken in, and how long each pair took to break in. We also performed a wet-surface test that allowed us to get a sense of how much traction and grip each boat shoe offered. Once armed with this information, we then proceeded to narrow our original shortlist down to a final list of what our research and testing proved to be the best boat shoes on the market. 

Model Measurements: Our model stands at roughly 6’1’ and wears a size US men’s 11 shoe. Consequently, all pairs were tested in this size (with a regular width).  

Thursday Boot Company Handsewn Loafer

Best Loafers Pick: Things like hand-worked construction and top-shelf materials typically come at a steep price. The Thursday Boot Company, however, has found a way to deliver an exceedingly high-quality pair for an exceedingly-accessible price, thanks to the brand applying the same value-laden, top-shelf formula from its work boots, Chelseas, and chukkas to a pair of classically-styled boat shoes — a process resulting in the plainly yet aptly-named Thursday Boot Company Handsewn Loafer. 

The Good

Made by hand in small batches in Mexico, the boots are crafted using a top-shelf single-piece construction that’s sewn together by hand. Because this construction technique and a process is typically reserved for some of the most premium pairs that money can buy, it’s really cool to see Thursday both employing this technique, and offering a pair born out of it for under the $150 mark. The shoes are crafted from a matte black leather with a soft yet slightly rough finish. The inside of the shoes feature antimicrobial shock absorbing insoles ad leather midsoles. The full leather midsole is also an appreciated — and premium — touch. 

The StormKing rubber lug outsoles that the shoes are built on provided the best traction and grip of all the pairs I tested — save for the Timberlands which pretty much blew everything else out of the water. The Poron insoles and both cushioned and shock-absorbing. My favorite aspect of the interior, however, is the fact that they’re equipped with antimicrobial properties, as it’s easy for leather-lined boat shoes to get sweaty and gross after being worn barefoot for an extended period. 

Thursday’s boat shoes feature a triple black color scheme with matte black leather uppers, blacked-out outsoles, and black stitching — plus they ship with matte black leather laces. While I opted for the pair with the available StormKing outsoles, Thursday does sell its boat shoes in a leather-outsole variant. 

Supplementary Strengths 

As far as craftsmanship and build quality goes, this pair’s didn’t look any worse than the pairs I tested costing two-times as much (if not more). That’s a pretty huge compliment considering their price, though this has seemingly be made possible by Thursday outsourcing its production to Mexico while still utilizing small-batch production, allowing its boat shoes to be sold with premium quality without the typically-premium price tag. 

Other than the bottom of the outsoles and the on the insoles, there’s zero logos or branding anywhere on these shoes whatsoever — another aspect of this boat shoe that I really like. Plus, when you factor in everything that you get — premium materials, involved construction techniques, and hand-worked manufacturing — this pair also offers pretty extraordinary bang-for-your-buck. 

The Not So Good

Though it’s undeniably a great pair, I did have a few issues with TBC’s Handsewn Loafer. I also found they took a bit longer than the other pairs I tested to break-in, and the first two-to-four weeks aren’t the most comfortable. A slightly softer set of leather laces would definitely allow for a more snug and easier-to-adjust fitment. I even swapped in a softer set from another pair I was testing and was able to dial-in the fit a lot better — making an already stellar boat shoe that much better. Fortunately, you can just order an aftermarket set of leather laces for this pair — and at their super accessible price, it’s pretty easy to justify this second purchase. 

Lastly, while the outsole does a pretty decent job of affording traction on wet and/or slick surfaces, the StormKing setup does add a decent amount of weight to the equation, resulting in them being the heaviest pair I tested, aside from maybe the Timberlands. I do think this pair’s many strengths more-than-outweigh any issues I have with them, but I still feel they’re worth mentioning. 

Verdict: If you’re after a pair of handcrafted, heirloom-grade boat shoes but aren’t looking to break the bank, no other contemporary men’s label offers a better option than Thursday Boot Co’s Handsewn Loafer, as it provides a top-shelf material selection, old-world construction techniques, and hand-worked craftsmanship into a comfortable, rugged, and value-laden boat shoe costing less than $150. 

Timberland 3-Eye Lug Handsewn Boat Shoe

Best Chunky Outsole Pick: Roughly four-and-a-half-decades after the boat shoe was first introduced, Timberland opted to get in on the boat shoe market. Instead of penning a traditional boat shoe design, Timberland decided to take a handful of its hallmark design traits and sneak them into a boat shoe design, all being placing the entire design atop one of its signature deep boot lug outsoles — a process that gave way to the 3-Eye Lug Handsewn Boat Shoe.

The Good

Timberland’s 3-Eye Lug Handsewn Boat Shoe boasts uppers that are are cut from genuine Horween leather and sewn together by hand. The boat shoe features three sets of gold-colored eyelets around the tongue, and perimeter eyelets around the ankle all fed with leather laces. Inside you’ve got a leather liner and a lightly-padded leather insole. A padded collar not only bolsters comfort, but it also conforms to the shape of the back of your foot over time with enough use. 

The build quality and fit and finish is surprisingly top-shelf. The craftsmanship looks meticulous and quality control standards appear to be extremely high. They also feel like the most rugged pair I tested — and by a pretty huge margin. Likewise, the outsole of these shoes offered what was hands-down the best traction and grip on wet surfaces out of every pair I tested — again, by a pretty humongous margin. 

 I also found them to be incredibly comfortable to wear barefoot. Additionally, this pair also only took around a week or two of wearing daily for them to feel completely broken in. From that point they only got more anymore comfortable as they continued to ever-so-slightly conform to my feet even more. 

Coming from a big brand utilizing mass production, you might not expect details like Horween leather constructions and hand-sewn craftsmanship, but this pair nonetheless delivers both — and does so while costing just $150. I also love the more authentic-looking retro aspect of this pair, which frankly makes sense considering they were first introduced in 1978 and little to nothing has been changed on them since. 

Supplementary Strengths

It’s also cool seeing Timberland subtly apply several of its signature design cues to a pair of boat shoes. On top of the visible work boot outsole, the boat shoes also sport gold-colored eyelets, a padded collar, and embossed tree logos. With the logos being small and the rest of the details being understated, it’s one of those things where only people that are really familiar with the brand will notice the details and put them together. 

Considering their Horween leather uppers and hand-sewn construction, this pair’s $150 price tag is beyond-reasonable, and I’d say this pair probably offers the best value or bang-for-your-buck out of every pair I tested, save for possibly Thursday Boot Co’s boat shoes. 

Part of me also appreciates Timberland’s “if it ain’t broke, don’t fix it” attitude, as their approach has  been taking the deep-lug outsoles from its rugged work boots and capping off the bottom of a pair of boat shoes with the exact same outsole. I was actually pretty surprised to run to my closet, grab my pair of Tims, and realized their outsoles were identical to those on the boat shoes I was testing. 

The Not So Good

I did find that these shoes were extremely heavy, which lowers their comfort just a bit, at least when worn all day. And, despite generally being a fan of the brand and owning several pairs, I don’t love how outwardly visible the outsole’s lug pattern is, or the Timberland logos adorning the outer-side of the uppers. With that said, I also acknowledge that, if you’re not a fan of the Timberland brand as a whole, you probably won’t be a fan of the myriad of its signature details that are integrated into this design. It’s also probably the least traditional take on boat shoes out of every pair I tested. 

Verdict: First debuting in 1978, the Timberland 3-Eye Lug Handsewn Boat Shoe is the result of the brand taking a host of its signature design cues — including its work boot outsole — and applying them to the creation of an ultra-rugged, hand-crafted boat moccasin that’s got unchanged since its introduction. 

Sebago Schooner

Best Work Shoe Pick: Before becoming bonafide style pieces, boat shoes were worn primarily for their utility, and as such were designed largely with a function-over-form approach. And while they may not be quite as fashion forward as their trendier-looking counterparts, these function-focused pairs still very much have their place in today’s pantheon of boat shoes. So, whether you’re looking for a more authentic-looking retro-inspired pair of a more utilitarian model boat shoe, the Sebago Schooner is an excellent pick. 

The Good

The Sebago Schoone is a traditional-looking boat shoe with a canoe moc construction that’s crafted from hot-stuffed leather that’s waxed and oiled before being sewn together by hand. Built atop non-marking, antislip, siped rubber outsoles, the Schoone also gets a leather sock lining, and two sets of eyelets over the tongue and a set of perimeter eyelets running around the collar of the ankle. Rounding out this pair is a matching set of leather laces. 

Once they’d eventually conformed to the contours and shape of my feet, I found this pair to be exceedingly comfortable — making the less-than-enjoyable break-in process well worth it. I was initially bothered by the lack of cushioning or foam on the insoles. After spending time testing some of the more thoroughly cushioned pairs, I found the foam or padding eventually broke in and gave way, loosing much of its cushioning properties. Sebago’s Schooner boat shoes, on the other hand, are designed with a more firm leather outsole that conforms to the bottom of your feet and offers what feels like a custom-fit for years and years without changing.

Supplementary Strengths

I had the same feeling about the leather insole only extending part of the way into the bottom of the shoe, with the area below the balls of your foot and forward being completely unlined and unfinished. Though it took some time, when this part of the shoe’s interior did break in, it made for a super comfortable wearing and walking experience. 

The build quality is pretty impressive and I appreciate the more involved process that Sebago opts for when making the Schooner. The traction and grip on this pair was acceptable, but they didn’t provide much confidence (or grip) on wet or slick surfaces. 

The Not So Good

While I genuinely think the Sebago Schooner is a terrific boat shoe, I did have a few complaints or areas that I felt could be improved. For starters, despite being marketed as waterproof, I found that water quickly found its way inside the toes of the shoes through the stitching. Second, the stitching along the back of the bottom of the heel on the inside of the shoe created a pretty major hotspot that took over a month to go away — meaning I could only comfortably wear this pair with socks on during that time. They also took the longest to break in out of every pair I tested, and were the least comfortable pair before eventually conforming to my feet.  

Third, the craftsmanship looked good, but the build quality could use improvement, as could the overall durability. Even after just a few weeks of testing, I found the outsoles start to want to separate from the rest of the shoe due to having fewer stitches and reinforcement than most of if not all of the other pairs I tested. Fourth, despite having a fairly involved groove patten, this pair’s outsoles didn’t provide much in the way of traction or grip when walking or standing on wet/slick surfaces. Fifth, with just two pairs of eyelets over the tongue, these boat shoes didn’t offer as much adjustability as some of the triple-set pairs I tested — plus the laces are pretty stiff, making adjustability that much harder. 

Verdict: Whether you’re looking for an authentic-looking retro-style pair or a utility-focused model capable of actually performing topside, the Sebago Schooner has you covered on both levels. 

Sperry Gold Cup Authentic Original Boat Shoe

Best Classic/Original Pick: In 1935, Paul Sperry introduced the world to the very first pair of what we now call boat shoes with the Sperry Top-Sider. After seeing his dog running on ice, he was inspired to cut sipes into the outsole of a pair of moccasin-style shoes, giving way to a comfortable piece of footwear that afforded enough grip to lend itself to top-side use. Fast-forward almost 90-years-later to today, and Sperry still produces a modern-day version of its original boat shoe, christened the Sperry Gold Cup Authentic Original Boat Shoe. 

The Good

As part of Sperry’s Gold Cup Collection, these shoes combine timeless retro designs with modern materials. Sewn together by hand, these shoes are pieced together around a set of full-grain leather uppers mated to a rubber outsole with a flat, half-inch heel. The interior of the shoe is also ridiculously soft and supple thanks to the use of a lambskin leather lining. Rounding out the original boat shoes are two sets of eyelets around the tongue, perimeter eyelets, and leather laces. 

The overall craftsmanship and build quality is impressive, especially considering the mass-produced nature of this pair — though that same nature plays a major role in the brand being able to sell their original boat shoe for below the $200 mark. This is just one of a myriad of strengths and highlights this pair demonstrated during the time I spent testing it. 

As far as logos and branding, there is embossed script on the side of the outsole reading “Sperry Top-Sider” a Sperry logo on the bottom of the outsole, and another Sperry logo positioned above “Gold Cup” script on the insole. The shoes also sport bespoke Sperry-branded metal eyelets which are no doubt a subtle yet cool — and premium — touch. None of these logos are details are at all visible to the naked eye, at least upon first glance. It’s not until actually holding the shoe up right in front of you that any of these details become apparent. In my opinion, this gives these boat shoes an even more classic, timeless feel. 

Supplementary Strengths

The Gold Cups are insanely comfortable right out of the box, and the shoes only become even comfier with time. They also do a phenomenal job of conforming to your feet. They feature what’s by far the best-cushioned insoles and the leather interior is easily the softest and most supple of every pair I wore. What’s more, the inside of the shoes are devoid of any ill-placed stitches or welts that cause hotspots and discomfort. 

As touched on above, in order to test our list of boat shoes, I broke each pair in by using them as my slippers and around-the-house/yard shoes. And after this testing was completed, I went right back to wearing the Sperry’s as my around-the-house shoe — despite owning several fantastic pairs of slippers. I feel like this speaks volumes about how wildly comfortable these boat shoes truly are. 

Like the Quoddy Head Boat Shoe, the leather laces on this pair of Sperry’s are rugged and robust, but no so stiff that they compromise the shoe’s adjustability or ability to achieve a snug, secure, and comfortable fitment. And, while it doesn’t actually impact their user experience or performance, I still think there’s definitely something to be said for the fact that Sperry is responsible for inventing the boat shoe and delivering the very first pair. As such, the band should always be considered when shopping in this space, after all, it’s hard to go wrong with an original like this. 

The Not So Good

One of the downsides to opting for an original pioneering product, is that their newer counterparts often find ways to evolve and improve upon the earlier designs, and it’s no different with boat shoes. As such, there are a few areas where the Sperry Gold Cups fell short. Starting with the non-marking soles, which leave a lot to be desired in terms of traction and grip — but no doubt out-performed the Quoddy Head Boat Shoe and the Sebago Schooner. 

The only other complaint I have about these shoes in the faux-worn/weathered toe. This fake bit of patina does add some character, but it also gives them a more worn and lived-in aesthetic that lightweight clashed with the cleaner, more fashion-forward outfits that I typically paired them with. It is worth noting that Sperry does make this pair in dark brown and navy color options, but the medium beige hue is by far my favorite, I just wish it was offered without the faux-worn toe. 

Verdict: The Sperry Gold Cup is a modern-day take on the very first boat shoe ever to hit the market. As the very piece of footwear responsible for creating the entire segment, this classic moccasin-style top-sider is always worth considering when shopping around for boat shoes. 

Quoddy Head Boat Shoe

Best US-Made Pick: With domestic, U.S. manufacturing, it’s difficult to compete with mass-produced operations overseas, as the sheer volume they generate goods in makes it exceedingly tricky to deliver products at anywhere close to the same price. As such, if you’re going to run a successful domestic manufacturing operation, you need to deliver a product with a level of overall quality that blows its foreign-made counterparts out of the water — which is exactly what we have here with the Quoddy Head Boat Shoe. 

The Good

Sporting a true moccasin construction, the Head Boat Shoe is cut from a soft leather that benefits from a pull-up process that bolsters color and increases sheen, giving each and every pair a more unique, one-of-a-kind look. The bright-white-colored outsoles also give this pair a slightly more modern aesthetic, without compromising their timeless boat shoe-look.  

I found the shoes did an incredible job of conforming to my feet. They’re comfortable right out of the box, but the wearing experience only gets better with time. They can also comfortable be worn with no-show socks or completely barefoot. The lining plays a massive role here, as, it may look unfinished, but actually feels pretty stellar on the skin. The unlined interior definitely decreases the time they take to dry if the interior gets wet, too. Around the tongue is a triple-eyelet set that uses alloy eyelets that are fortified via a rust-preventing lacquer. 

The insoles are lightly padded but feature the softest-feeling leather out of any part of any shoe I tested. Unlike some pairs with thicker foam or padding that eventually wears down and gives in, the minimal padding of this pair allows it to offer the same feel for years — which isn’t a problem as they conform to your feet and offer ample comfort. 

Supplementary Strengths

Considering this pair is made in small batches in workshops in Maine, I was in no way surprised to see they exhibited the best build quality and craftsmanship out of all the pairs I tested. Every piece of leather and every tiny stitch and detail looked perfect. I also love that these boat shoes can be re-soled, allowing you to have a new outsole sewn on if you wear the original one out — or enabling you to swap in a grippier set if you aren’t satisfied with the stock outsole’s traction. 

Unlike some of the pairs I tested that use stiffer, more robust leather laces, the Quoddy Head Boat Shoe’s set of laces are made from Rawhide leather but are soft and flexible enough to be able to actually deliver adjustability. The laces also run around the back of the heel and do a great job of tightening the shoe’s entire fitment. 

At around $250, it may at first seem like this pair doesn’t offer the best bang-for-your-buck, but I assure you that you’re getting more than you pay for here, as this pair is extremely comfortable, cut from premium materials, and boasts an overall level of craftsmanship and construction that’s second to none. They can also be re-soled, allowing them to be worn for years to come — making it even easier to justify their price tag. For those looking for a more bespoke option, Quoddy also sells this pair for $349 in a custom made-to-order version that let’s you selection your leather color, sole type, thread hue, hardware metal, laces, and liner material and color. 

The Not So Good

I also found the off white color of the outsoles to be super prone to taking on scuffs and dark smudges, which can seriously take away from their otherwise smart and clean look. Fortunately, with just a tiny bit of Mr. Clean. Magic Eraser or Shoelada Sole Cream, I was able to return the soles to their former glory — a process I had to repeat every few weeks depending on how often I wore them. Unlike some of the brand’s other moccasin-style loafers, Quoddy’s Head Boat Shoe doesn’t use a Vibram rubber outsole, and the pair’s traction and grip simply leaves a lot to be desired — especially in the wet. So, if you just plan on wearing them for their appearance this won’t be a problem, but if you actually plan on using them top-side, you may want to look for other pairs — or have this pair fitted with a different outsole or built on a made-to-order basis from Quoddy who offers the MTO version with an available lug sole outsole. 

Verdict: The Quoddy Head Boat Shoe is a top-shelf and modern take on this style of footwear that combines contemporary designs and premium materials with small-batch production proudly carried out in Maine. Though they do cost a bit more, these re-soleable boat shoes truly are worth every penny. 

Boat Shoes Comparison Chart

What Are Boat Shoes For?

Hailing from the northeast, boat shoes were invented by Connecticut native Paul Sperry (the creator of Sperry) after he carved siping (akin to car tires) on the soles of his shoes. This provided better traction on wet surfaces, ideal for the deck of a boat, but since the 70s these shoes have been breaking into fashion territory. That doesn’t mean the utility from the original design is lost, but fashion and comfort have become equally important (if not more) than having solid traction on wet surfaces and boat decks. While most boat shoes will have waterproof leather, an outsole built for traction, durable stitching, and wraparound lacing, these days they’re worn for fashion a bit more than they are for actual boating.

What To Consider When Shopping 

There’s a plethora of areas one could focus on when shopping for boat shoes, though the reality is that there are really just half-a-dozen factors that you really need to pay attention to — all of which we’ll be briefly breaking down directly below. 

Insole & Footbed: You’ll also want to pay attention to the types and materials of the foot-bed and insole of any pair of boat shoes. Additionally, you’ll also want to review if the uppers are lined or unlined, as all of these areas can impact comfort and how long they take to break in. 

Materials: Canvas, suede, and leather are the main materials of this classically-styled shoe — with the latter being the most common — along with the rubber outsole. Since they’re generally meant to be worn without socks, some variants might feature a soft lining inside.

Build Quality: It’s not just the materials used to make a boat shoe that matter, but also the manner in which those materials were pieced together, as the construction techniques and build quality can hugely impact overall quality and performance — and these areas play a pivotal role in distinguishing cheaper pairs of boat shoes from their more premium, meticulously-crafted counterparts. Many of today’s best pairs are also sewn by hand. 

Waterproofing: Every good pair of boat shoes will have waterproof (usually via oil) canvas or leather. Sometimes slipper or moccasin hybrids may have a softer material, like suede, but even then it will usually be waterproofed as well. If you’re going to be using these shoes for some real boating, it’s essential that they’re waterproofed, but if you’re looking for casual comfort, it may not be as important.

Outsole: A durable non-marking rubber outsole with siping is another cornerstone of a good boat shoe, but similar to waterproofing, if you’re not boating then these details aren’t as important. If you are, however, a white outsole with a siping pattern is recommended for traction and to prevent scuffing the deck.

Price & Value: Obviously, not all boat shoes are created equal, and as such these pieces of footwear can massively vary in terms of price. While you do typically get what you pay for, there are still some pairs that offer much, much, much better bang-for-your-buck than others, making this a crucial area to review if you’re shopping on a tight budget. 

Honorable Mentions

The Yuketen Blucher Cortina are a premium piece of full-grain leather footwear that combines design traits from boat shoes and moccasins into a single cohesive shoe. With a pebbled leather construction, fringed details, and a chunky deep-lug outsole, this pair boasts a unique take on this more traditional style of shoe. While its materials and build quality are exceptional, this pair simply comes at a very steep price, prompting us to include it only as an honorable mention. 

Another simple yet classic option when acquiring a pair of boat shoes is the Ralph Lauren Merton Leather Boat Shoe. Priced at under $140, this value-laden pair offers a premium material selection and great craftsmanship at a super accessible price. Because it was beaten out by Sperry’s original pair of boat shoes and Quoddy’s Head Boat Shoe, Ralph Lauren’s boat shoe has been relegated to a particularly honorable mention. 

Taking its monicker from the river of the same name, Easymoc’s Merrimack Boat Shoe and an ultra-unique interpretation on the segment that infuses traditional boat shoe designs with elements from sneakers and running shoes. Though it is meticulously pieced together from premium materials, the unconventional, unorthodox, and frankly unusual nature of this top-shelf pair made us decide to include it only as an honorable mention. 

Cut from suede, the Rancourt & Co. X J.Crew Gilman Camp-mocs are a premium pair of boat shoes that are as stylish and well-made as they are comfortable and timeless-looking. Sadly, this pair was (and at least as of the time of writing, continues to be) out of stock, and as such we were enable to source a pair for testing and review, tying our hands and forcing us to relegate this pair to a very honorable mention — though it almost certainly would’ve been included had we been able to get our hands-on a pair. 

Tested: The Best Men’s Chelsea Boots for Any Occasion

Want to check out another type of traditional men’s footwear that’s once again in-vogue? Then be sure to cruise on over to our guide to the best Chelsea Boots for a curated selection of the space’s latest and greatest options.