Boat Shoes Are Our Favorite Easy-To-Wear Transitional Shoe for 2021

Scarosso Jude Boat Shoe
Courtesy of Scarosso
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If you’re a young guy, then either you or your friend (or both of you) have at least one pair of boat shoes. That’s because the best boat shoes are stylish, easy to dress up or down depending on whatever you’re doing and make some of the best men’s slip-on shoes. Not to mention, even the cheap ones tend to be made of durable materials like leather with rubber soles, so they’ll take care of you as long as you take care of them.

If you’re new to the boat shoe train, it can be hard to know where to begin. Yeah, you’ve probably heard of Sperry, but everybody has Sperrys and there are so many great boat shoes out there besides them.

That’s where we can help. We’ve gathered some of the best boat shoes online here in one list. We’re familiar with and have owned shoes from all of these brands and they will all deliver the stylish boat shoe you’re looking for with their own twists on the classic style.

Ready to get started? Check out some of the best boat shoes below. They’re versatile enough for the office or a date, but they’re casual enough to wear on weekends in the city or at the boardwalk, so no matter which boat shoe you go with, you’re going to be choosing a winner.


The Best Sperry Boat Shoes

We’re sorry to have to lead with Sperry and it may be the stereotypical shoe of New England prep wear, but when you think of boat shoes, you think of Sperry. That’s because Sperry practically single-handedly ignited the boat shoe trend through its high quality and variety of stylish boat shoes. And to be fair, Paul Sperry invented the world’s first boat shoe in 1935 to prevent slipping on deck. That’s why we couldn’t talk about the best boat shoes without throwing at least one pair of Sperrys your way.

Of course, given the variety of Sperry’s boat shoe offerings, it’s an impossible task to pick just one great pair. That’s why we went through Sperry’s more than 130 styles and picked multiple styles that it seems only Sperry could make.


1. Sperry Gold Cup Handcrafted in Maine Tri-Tone Boat Shoe

For our first pick, we wanted something strong for the best boat shoes. Scrolling through the Sperry website, there was one shoe that stood out among all others: the Men’s Gold Cup Handcrafted in Maine Authentic Original Tri-Tone Boat Shoe. The “Handcrafted in Maine” part of the name indicates this is Sperry’s premium line of shoes and this shoe absolutely delivers.

It uses leather from the Horween Leather Company, one of the best and oldest continuously running tanneries in the US. The shoes are hand punctured and stitched and incorporate Vibram soles for traction and top-quality perforated leather linings for supreme softness, breathability and comfort. But what really brings these shoes together is the tri-tone color scheme of red, ivory and navy. Nothing’s more awesome or more American or more boat shoe than handmade shoes in America in the good old red, white and blue.

Sperry Gold Cup Handcrafted in Maine Tri-Tone Boat Shoe Courtesy of Sperry

Sperry Gold Cup Handcrafted in Maine Tri-Tone Boat Shoe



2. Sperry Men’s Gold Cup Handcrafted in Maine Authentic Original Boat Shoe

So you want premium Sperry boat shoes, but perhaps you’re not feeling the red, white and blue leather? That’s cool, just go for the identical Men’s Gold Cup Handcrafted in Maine Authentic Original Boat Shoe. These boast all the same high-quality materials and come in far more traditional colorways like brown, blue and natural.

Sperry Men's Gold Cup Handcrafted in Maine Authentic Original Boat Shoe, best boat shoes Courtesy of Sperry

Men's Gold Cup Handcrafted in Maine Authentic Original Boat Shoe



3. Sperry Men’s Bahama II Sneaker

Part boat shoe, part sneaker, these canvas shoes from Sperry are a decidedly more casual alternative to the traditional leather boat shoe. The flat rubber sole and canvas upper makes them feel look like your Vans, while the lacing system and moccasin toe bear the unmistakable look of a boat shoe. There are a variety of color options, but clean and classic white is hard to beat.

Sperry Men's Bahama II Sneaker, best boat shoe Image Courtesy of Sperry

Sperry Bahama Sneaker


4. Sperry Gold Cup Orleans Boat Shoe

Next up from Sperry, we wanted to go for something classic that was a bit more affordable while still utilizing premium materials. You can’t go wrong with the Men’s Gold Cup Authentic Original Orleans Boat Shoe. This shoe uses full-grain leather uppers with lambskin linings and the typical rawhide laces.

Add in a cushioned heel cup, an Ortholite insert for the footbed and a latex outsole with siping and you’ve got one comfortable, durable, forever-stylish shoe for hitting the bricks or the upscale restaurant. You can’t go wrong with the gorgeous brown amaretto color, but the black and grey versions are just as useful.

Sperry Orleans boat shoe, best boat shoes Courtesy of Sperry

Sperry Gold Cup Orleans Boat Shoe



5. Sperry Men’s Authentic Original Float Boat Shoe

We’ve given you some of Sperry’s absolute best, most premium options, but what about something a little more directly useful for water?

The new Sperry Men’s Authentic Original Float Boat Shoe is a boat shoe designed to, yup, float in water, and it’s perfect for beaches and general spring and summer weather.

These boat shoes are made from an EVA material, so they’re super light, buoyant and waterproof. Size down a half size for the best fit and never lose your shoes on the water or deal with soaked steps again. Try wearing it on beach days for summer 2021 — you won’t regret it.

Sperry Men's Float Boat Shoe, best boat shoes Courtesy of Sperry

Sperry Men’s Authentic Original Float Boat Shoe



6. Rowing Blazers x Sperry Lug Sole Boat Shoe

Stock on these is very limited, but they’re too cool not to include. Rowing Blazers added their twisted take on prep to the classic Sperry boat shoe, and the result is anything but traditional. These shoes have a thick lug sole and a color-blocked design. Rowing Blazers also swapped out traditional leather for nylon. The white lug soles are Vibram, so these boots are built to last.

Rowing Blazers x Sperry Lug Sole Boat Shoe, best boat shoe Image Courtesy of Rowing Blazers

Sperry Rowing Blazers Boat Shoe


7. Sperry Men’s Authentic Original 2-Eye Boat Shoe

Sperry boat shoes are plenty preppy as it is, but could they get any preppier? Turns out the answer is yes. These boat shoes feature a nautical flag motif across the upper. These are made from canvas, rather than leather, meaning they’ll be as comfortable as your favorite casual sneakers.

Sperry Men's Authentic Original 2-Eye Boat Shoe, best boat shoe Image Courtesy of Amazon

Sperry Boat Shoe

$53.42 $85.00 37% OFF

8. Sperry Men’s Authentic Original Whisper Boat Shoes

It might seem like every pair of Sperrys is the same, but the devil’s in the details. The Men’s Authentic Original Whisper Boat Shoes were designed with superior softness in mind. To that end, they use ultrasoft, lightweight full-grain leather that protects your foot without giving it the blisters common from stiffer leathers, and a blister-free man has got to be a happy one.

Sperry Men's Whispher Boat Shoe Courtesy of Sperry

Men’s Authentic Original Whisper Boat Shoes



9. Sperry Plushwave Boat Shoe

We wanted something from Sperry that prioritized comfort above all else because hey, no matter what any shoe manufacturer says, any leather shoe can get uncomfortable after a day of walking. That’s what Sperry set out to fix with its Men’s Authentic Original Plushwave Boat Shoe. You get the full-grain leather and laces you expect from Sperry, but this shoe uses what Sperry calls Plushwave technology, an ultra-light, cushiony, bouncy sole to keep your foot from getting tired while footing it around the city. We think the tan color will give you the most versatility, but honestly, the brown, navy and oatmeal colors will work with a million outfits too.

Sperry plushwave boat shoe Courtesy of Sperry

Sperry Plushwave Boat Shoe



10. Sperry Men’s Authentic Original Kick Down Boat Shoes

These next Sperrys won’t be any more useful near the water, but the Men’s Authentic Original Kick Down Boat Shoes make going from spiffy to casual (or casual to spiffy) incredibly easy. These boat shoes have a “kick down” heel, so you can keep the heel up for the full boat shoe look or flip them down for more casual slip-ons. Soft nubuck uppers take care of your foot and an Ortholite cushion keeps your sole happy for an all-around winner of a boat shoe.

Sperry Men's Kick Down Boat Shoe, best boat shoes Courtesy of Sperry

Sperry Men’s Authentic Original Kick Down Boat Shoes



The Best Alternative Boat Shoe Brands

While we lead with Sperry, you shouldn’t think they’re the only name in boat shoes. They may be the standard but trust us, there are plenty of incredible brands out there making worthwhile Sperry contenders.

Don’t believe us? Take a look through the rest of our list of the best boat shoes for men below!


11. Quoddy Classic Boat Shoe

If you only want the best boat shoes, then you need to go to Quoddy. What the brand lacks in variety it makes up in quality, timeless design and customer service.

One of the brand’s unique offerings is a design-your-own boat shoe option where you can pick every aspect of Quoddy’s Classic Boat Shoe, including the upper leather color, the kind and color of sole, the thread color, the hardware color for the three eyelets, the lace color and the lining color. It’s almost like making it yourself, except you lack 80 years of experience in making high-quality footwear by hand.

But if you don’t want to go through that process, Quoddy has in-stock options of its Classic Boat Shoe, including a whiskey leather color option.

Because Quoddy is in the business of premium boat shoes, they’re also in the business of premium customer service, too. If you wear down the sole of your boat shoe or beat the leather up over years of wear, you can send it off to Quoddy for repair and resoling for a fee. Your shoes will be like new again, except they’re already broken in.

Quoddy classic boat shoe Courtesy of Quoddy

Quoddy Classic Boat Shoe



12. Timberland Handsewn Lug Shoes

These boat shoes come from Timberland, a brand best known for their rugged, street-ready boots. That’s why it’s no surprise their boat shoes are similarly tough. They have a thick lug made from rubber, giving these shoes ample traction and a tough look. The uppers are made from leather. These aren’t the kinds of shoes you’re likely to see in Nantucket, but that’s not a bad thing.

best boat shoe -Timberland Handsewn Lug Shoes Image Courtesy of Timberland

Timberland Boat Shoe


13. L.L. Bean Men’s Casco Bay Boat Mocs

If you haven’t picked up on a trend yet, Maine makes the best boat shoes in the world. L.L. Bean is both an inheritor and a carrier of that tradition, and its Men’s Casco Bay Boat Mocs are top-notch. The Casco Bay Boat Mocs are, as the name implies, a true cross between boat shoes and moccasins. They’ll handle boating and fishing, but are comfortable enough for hanging in the backyard too. An all-leather upper and leather lining keep things durable and comfortable while a siped rubber outsole keeps sliding on wet surfaces to a minimum.

L.L. Bean Casco Bay boat mocs Courtesy of L.L. Bean

L.L. Bean Men's Casco Bay Boat Mocs



14. G.H. Bass & Co. Jetty Lug boat shoes

G.H. Bass is credited with inventing the penny loafer, so it’s no surprise that a boat shoe is well within their wheelhouse. But what might be surprising to some is that these boat shoes are anything but stuffy — the thick lug sole and vibrant orange color make these a high fashion alternative to the standard boat shoe.

G.H. Bass & Co. Jetty Lug boat shoes, best boat shoe Image Courtesy of Farfetch

GH Bass Boat Shoe


15. Rancourt Read Boat Shoe

Rancourt is yet another made-in-Maine shoe company, but hey, it’s not a bad thing to have a region that clearly makes the best boat shoes. We love the Rancourt Read Boat Shoe. In addition to the normal trappings of the best boat shoes, such as Horween Chromexcel leather, a great benefit to these shoes is the ability to choose a shoe width. You can stop pretending your feet fit into other narrower boat shoes and finally get the shoe width you need. Unfortunately, these boat shoes are made to order, so it’ll be some time before you get them, but they’re worth the wait.

Rancourt Read boat shoe Courtesy of Rancourt

Rancourt Read Boat Shoe



16. Timberland + Aimé Leon Dore 3-Eye Lug Nubuck Boat Shoes

Timberland linked up with streetwear label Aimé Leon Dore on a stylish take on its classic 3-eye lug sole boat shoe. Aimé Leon Dore recognizes when to leave perfection alone, which is why the brand simply swapped out the colorway and material on these and left the design of the shoe pretty much untouched.

best boat shoes - Timberland + Aimé Leon Dore 3-Eye Lug Nubuck Boat Shoes Image Courtesy of Mr Porter

Timberland Aime Leon Dore Boat Shoe




17. Allen Edmonds Force 10 Chromexcel Men’s Boat Shoes

Allen Edmonds may be known for its fancy leather dress shoes, but the brand’s shoe know-how goes beyond Oxfords and Derbys. The Allen Edmonds Force 10 Chromexcel Men’s Boat Shoes deliver on AE’s quality promise too. The leather will age beautifully over time, and the three-layered sole makes these boat shoes perfect for walking in comfort and style.

Allen Edmonds Force 10 Boat Shoe with Chromexcel Leather Courtesy of Allen Edmonds

Allen Edmonds Force 10 Chromexcel Men's Boat Shoes



18. Eastland Men’s Seaquest Boat Shoe

For the last of the Maine-based boat shoemakers, we turn to Eastland. A family-owned business since 1955, Eastland shoes are high-quality without the $200-plus price tag. The Eastland Men’s Seaquest Boat Shoe is one of the brand’s most popular options for its basic boat shoe appeal, leather upper and memory foam insole.

Eastland Men's Seaquest Boat Shoe Courtesy of Zappos

Eastland Men's Seaquest Boat Shoe



19. Sebago Men’s Docksides Boat Shoes

Moving out of Maine (finally, we know) to Michigan, you can find Sebago, one of the more popular brands of boat shoemakers. (Don’t worry, Sebago still draws inspiration from Portland). The full-leather Sebago Men’s Docksides Boat Shoes break in easily for fast comfort and they’ll stand up to years of wear and tear at a reasonable boat shoe price.

Sebago Men’s Docksides Boat Shoes Courtesy of Amazon

Sebago Men’s Docksides Boat Shoes



20. Marks and Spencer Leather Boat Shoe

Staying in the UK, Marks & Spencer makes straightforward shoes inspired by simple, classic designs. That’s what you get in the Marks and Spencer Leather Boat Shoe. The leather is soft and comfortable and ready to wear right out of the box, and a classic siped sole will help give you extra traction and slip-prevention you need.

Pick these up in a classic tan, which is more of a light brown, or a dark navy blue. Or treat yourself and buy one of each and you’ll always have a classed-up boat shoe option for every outfit.

Marks and Spencer boat shoe Courtesy of Marks and Spencer

Marks and Spencer Leather Boat Shoe



21. Clarks Un Pilot Lace Boat Shoes

Not everything Clarks does is a home run, but they do a few staples extremely well, including boat shoes. The Clarks Un Pilot Lace Boat Shoes are a textbook example of a solid boat shoe. The shoes are made from leather, use a lightweight rubber outsole and feature a soft footbed and textile lining for comfort. You probably won’t turn heads, but you will have pretty durable boat shoes that didn’t break the bank.

Clarks Un Pilot Lace Boat Shoes Courtesy of Zappos

Clarks Un Pilot Lace Boat Shoes



22. Cole Haan Men’s Pinch Weekender Camp Moc Loafer


While leather looks good and lasts, if a leather shoe doesn’t fit your foot right, you’ve got a one-way ticket to Blister City. That’s why you might consider a canvas boat shoe like the Cole Haan Men’s Pinch Weekender Camp Moc Loafer. Canvas, as a textile, can be more forgiving than leather and is, therefore, less likely to rub you the wrong way. Plus, canvas is generally cheaper than leather — barring absurd branding mark-ups — which is always a win.

Cole Haan Men's Pinch Weekender Camp Moc Loafer, best boat shoes Courtesy of Cole Haan

Cole Haan Men’s Pinch Weekender Camp Moc Loafer



23. Frye Mayer Boat Shoe

Frye makes some of the prettiest pairs of boat shoes the world ever did see. Like, come on, just take a peak at the Mayer boat shoes down below and you’ll understand what it is we’re talking about. These boat shoes are not only handsome, they’re designed to keep your feet comfy and cozy day in and day out. They have a contoured footbed with arch support to help keep your foot safe from blistering or any arch-related issues. They’re even fully leather lined to keep your handsomeness in check.

Frye Mayer Boat Shoe Courtesy of Frye

Frye Mayer Boat Shoe



24. River Island Chunky Boat Shoes

We know what you’re thinking and yes, a lot of boat shoes look kind of similar. The classic design has a timeless appeal that nobody tinkers with too much, but there is some room in that design for tweaks. Enter River Island Chunky Boat Shoes from the United Kingdom and ASOS. These brown suede boat shoes have a chunky rubber sole for added traction but mostly for a bit of street flair on what is typically a pretty conservative-looking shoe. Plus, the suede upper is super soft so you’ll be styling in comfort too.

River Island chunky boat shoe Courtesy of ASOS

River Island Chunky Boat Shoes



25. Scarosso Jude Boat Shoe

These Italian-made boat shoes are some of the most gorgeous we’ve ever seen. Full-throttle head-turners. They’re covered in a honey color that will make you drip in finesse and have a 360-degree lacing system that keeps your feet inside the shoe. They’re handcrafted to be the best they can be and will look great with just about anything in your wardrobe.

Scarosso Jude Boat Shoe Courtesy of Scarosso

Scarosso Jude Boat Shoe



How Should You Wear Boat Shoes?

Boat shoes are the epitome of summerwear. Obviously, given the name, boat shoes were initially a go-to shoe to wear for boating, but they’ve become very stylish in the men’s summer fashion space. With that said, boat shoes don’t make so much sense to wear during fall or winter. You can get away with wearing them in the latter half of spring, but the best boat shoes are made for summer. It’s important to note that if you’re actually wearing them for boating, they do have to meet certain standards. Specifically, you’ll need to ensure that the soles are non-marking. Some of the options on our list are more for style than seafaring, as the soles may not be deck-approved.

Boat shoes look great with flowy button-down shirts, short chino shorts or rolled chino pants and a pair of handsome sunglasses. If you’re really trying to spice up your outfit here, consider even topping your look with a fedora if you can pull it off.

How Do You Tie Boat Shoes?

The best boat shoes can be a little difficult to tie because of their material. Most of the time, boat shoes will use flat, leather laces that are on the shorter side. There really isn’t a tip to tie these kinds of laces aside from one: patience. Don’t allow yourself to get too frustrated when tying the best boat shoes or you might break a lace. Nobody wants to break a lace.


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