The Best Boat Shoes for Men Who Promise Not to Wear Them to Weddings
Our editors independently select the products we recommend. We may earn a commission on items bought through our links.
Paul Sperry, who had previously been selling duck decoys to outfitters like Abercrombie and Fitch, came up with the idea for boat shoes in 1935 after watching his dog pad happily across slippery and icy terrain. Using a knife, he cut grooves in his shoes so they’d more closely resemble paws. Despite the mythology surrounding Sperry falling off his sailboat into the long island sound, the first Sperry Top-Siders were created on the mainland. Sperry’s patent was for a non-slip sole.
Today's Top Deals
Sperry’s shoes quickly caught on with the U.S. Navy—mid-shippmen love a no-slip solution— and the good people of Connecticut, who love the son of a prominent family. Over the course of the next half century, Top-Siders became a preppy staple and boat shoes became a major part of the sizable New England footwear industry, which was expanding rapidly in Maine.
Boat shoes remain popular because they are a practical, wearable alternative to the loafer. They don’t look out of place at a cocktail party (unless it’s in Austin) and they slip on easily for a quick errand. Because of their ease, they’re often overused too. They show up uninvited to weddings, escorted by men who mistake them for acceptable formalwear. In truth, they are really an original alternative to moccasins that has become a modern alternative to sneakers and sandals, not monkstraps.
As preppy style continues to find its way back into the cultural zeitgeist, much in part to Gen Z’s revival of early 2000’s fashion combined with the ever growing popularity of retro-street style, new versions of boat shoes continue to pop up. This is why Sperry keeps announcing collabs, including the likes of Rowing Blazers, and in crazy colors and new materials. The Top-Sider is a “knockaround” shoe, even when it’s cordovan and even when there’s fringe involved.
What Experts Say
George Laboda, classic men’s style expert of Atlas & Mason and founding member of Gents’ Lounge, confirms that boat shoes are the safest option for a semi-casual spring/summer shoe. They won’t set you apart like a huarache or espadrille, but they will get the job done. Parker York Smith, another impactful influencer and stylist helping his audience find confidence with their own closets, believes that boat shoes have a place along coastlines but find a harder time fitting in among other settings.
Both stylists agree that pairing boat shoes with linen pants or shorts and camp collar shirts or knit polos updates their typical fraternity brother aesthetic and trades it in for something more grown up. Both also brought up the chunkier sole versions of the shoes, like the Rowing Blazers x Sperry collab, for more modern styling. And unless your wedding is on a boat, they recommend skipping boat shoes for that occasion since they are a casual shoe.
The Best Boat Shoes for Men
You’ll notice this list is stacked with the best Sperry boat shoes for men, but it does have some favorites from close competitors. This includes everything from classics to refreshed designs.
BEST OVERALL
Men's Authentic Original™ Boat Shoe
Buy Now
These are the Sperry mainstays. They come with the 360° LACING SYSTEM™, WAVE-SIPING™ for better traction, and are hand-sewn in the classic moccasin style. The leather is premium and may take a little break-in time, but with some wear, they become even more of a good fit for your fit. They also come in a variety of colors to meet your needs.
These are, in the SPY team’s opinion, the boat shoe go-tos. Their low profile design makes them perfect for casual spring/summer styling like Laboda and Smith mentioned. The loafer design makes them tempting as a wedding shoe option, but the team still advises against it. Keep these as an alternative to a sneaker instead.
BEST CASUAL OPTION
Men's Authentic Original™ Cross Lace Boat Shoe
Buy Now
This is another great, classic option that’s a bit dressed down from the Originals. The pre-worn feel of these boat shoes in particular give them an easy, cool, lived-in design. These would be perfect beach day shoes.
BEST VEGAN-LEATHER OPTION
Men's Authentic Original™ Veg Re-Tan Leather Boat Shoe
Buy Now
Sperry served up an option that captures the same great style as their original boat shoes, but with a Vegan twist. The sole of this Sperry option offers a little something extra. The speckled design sets it apart from the originals, but also does serve as a reminder of their Vegan construction for a cool conversation starter.
BEST FOR DAD SHOE ENTHUSIASTS
Men's Gold Cup™ Billfish™ PLUSHWAVE™ Boat Shoe
Buy Now
Laboda recommends a chunkier sole for a more modern look. If the chunky dad-sneaker is your jam, why not do it all the way with a dad-style boat shoe too? Comfort and style can share the same sole. If styling these with shorts evokes a little too much “country-club dad,” pairing them with a baggier denim will make them feel like a fresh throwback that Gen Z would be proud of.
BEST NEUTRAL COLOR OPTION
Men's Authentic Original™ Whitewashed Boat Shoe
Buy Now
Sperry could have just released leather boat shoes in standard colors: tan, black, dark brown, etc. Instead, they’ve created a whole slew of color options. Just like finding Crocs in every living color, Sperry made it possible to find boat shoes in most colors to suit any fancy. These de-saturated shoes add more uniqueness to the category. The lighter tones with this version of boat shoes lend themselves even more to summer styling. Like our style experts mentioned, think light linens and knit polos for a grown-up casual vacation look.
BEST MATERIALS
Unisex Cloud Authentic Original™ 3-Eye Vibram Boat Shoe
Buy Now
Not every boat shoe is made to look the same. Notice the eyelets are simplified to make room for a showstopper of a sole. The lug sole gives it some height and modern beefiness. Smith says that while he’s not sure if a lug-sole negates the whole boat shoe aesthetic, it is something that he’s more drawn to. These definitely have the modern, street style touch that Sperry is introducing into new styles and collabs.
BEST BRAND COLLAB OPTION
Unisex Sperry x Rowing Blazers Cloud Authentic Original™ 3-Eye Vibram Boat Shoe
Buy Now
This version of the boat shoe kicks up the street style a few notches. The corduroy upper, hiking laces, vibram sole, and heel tab details combine design elements that may otherwise have no business working together, but that’s the beauty of collaboration and street style influence. Laboda called these out as textured upper and chunky sole perfection, and for someone who’s an expert in classic style, that’s a big shoutout. A revitalized version of prep style is currently being adopted by street style and retro enthusiasts alike. Rowing Blazers does a good job of breathing life back into old off-limits prep style, making this collaboration an impressive boat shoe refresh.
BEST FOR DECKHANDS
Men's Authentic Original™ Float Boat Shoe
Buy Now
They’re made for guys who are actually planning on spending their time on boats or near docks. These are for the guys who need Crocs, but don’t actually like Crocs. Rather than add a bunch of new features, Sperry went back to the core functionality and design for their shoes: non-slip made to get wet. Paul Sperry would be proud.
BEST COMFORT SOLE
Men's Authentic Original™ Vibram 3-Eye Boat Shoe
Buy Now
A Vibram® Sole makes everything more comfortable. Vibram is an Italian company that makes a particular type of rubber sole. Originally made for better hiking shoes, these kinds of soles are now adopted to various types of boots and shoes for more comfort and a unique design. Adding a Vibram® sole to a boat shoe is the natural progression.
BEST FOR SNEAKER-WEARERS
Men's Bahama II Sneaker
Buy Now
They’re made for those who need an even more casual alternative to boat shoes. This style still incorporates the moccasin construction, but updates it with a twill upper and a rubber outsole. If regular boat shoes didn’t make the wedding invite list, then these should be left to your most casual outings. If there’s a gap in your wardrobe between sneakers and summer shoes, let these Sperry sneakers be the bridge.
BEST FOR MOCCASIN LOVERS
Rancourt & Company Classic Ranger-moc
Buy Now
They’re made for guys who want to come as close as they can to dress shoes with a moccasin/boat shoe-style shoe without actually hitting it. The quality of the leather elevates these over some of the competitor options, but the overall moccasin style keeps them in the semi-casual category. If you felt compelled to wear denim, a button-up shirt, and a blazer with boat shoes, these would be the ones to pair with. However, if you catch side-eye from any dress-code enforcers, you didn’t get this from us.
BEST SUEDE OPTION
Sebago Rossisland Jib Shadow
Buy Now
Laboda said that these were a great [nubuck] option with a bit of color variation. Nubuck isn’t a typical boat shoe option because of it’s poor reaction to water, but if you’re looking for something with more texture that still looks like a boat shoe, these are a solid choice. The nubuck leather leans more towards moccasin than boat shoe, but it also shows just how closely the two show designs are related. There’s a bit of ruggedness that comes along with a texture leather as opposed to a smooth finish.
BEST DRIVING LOAFER LOOK
QuoddyMen’s Canoe Shoe: Brown Pebble
Buy Now
They’re made for the guy who wants old money prep with a driving loafer silhouette, but new money casual style with some boat shoe flavor. Pebbled leather on the upper definitely elevates the shoe. It’s a nice juxtaposition against a more matte Vibram® sole.
BEST PREPPY OPTION
Polo Ralph Lauren Bienne Tumbled Leather Boat Shoes
Buy Now
Laboda and Smith both mentioned linen pants/shorts as staple boat shoe companions. The low profile and worn leather makes these excellent selections for a smart casual linen and knit polo outfit. Polo Ralph Lauren’s brand is synonymous with elevated, classic style. The construction of these boat shoes in particular carries an air of that elegance. If you want boat shoes that feel more dressed up, look no further.
BEST DESIGNER OPTION
Yuketen Boat Shoe DB with Lug Sole – C Whisky
Buy Now
They’re made for the guy who’s at the forefront of edgy and trendy fashion. This brings in the chunky sole element that Laboda said he loved in other versions of boat shoes but with even more attractive detail. The heavy moccasin stitching as well as the additional stitching around the body of this boat shoe set it apart. This is the intersection of prep, rugged, and street style that feels on trend right now.
MOST COMFORTABLE
Eastland Men's Yarmouth Camp Moc Slip On
Buy Now at eastland
Buy Now On Amazon
Eastland crafted these boat shoes-moccasin hybrids with their Eastland Exclusive Active Memory Foam insole, which means boat shoes just got more comfortable. Rather than revolutionize design, making a boat shoe that is more comfortable could be the better move. As many brands try to “innovate” to stay relevant, keeping things simple and comfortable is the way to many classic style lovers’ hearts.
BEST BUDGET OPTION
Reef CUSHION COAST TEXTILE
Buy Now
They’re for the guy who hates sandals and even boat shoes, but still needs something to wear to the beach or the dock. These are the least boat shoe-looking options on the list. If you’re still not convinced that boat shoes have a place in your current wardrobe, let these be your foray into dock-friendly footwear. The moccasin construction still echoes the boat shoe-style, but the textile upper and memory foam sole give you something different.
Proceed to Check Out:
https://spy.com/articles/gear/style/comfortable-dress-shoes-1202783140/
https://spy.com/feature/how-to-get-rid-of-shoe-odor-smelly-shoes-123598/
https://spy.com/articles/hacks/home-hacks/best-under-bed-shoe-organizer-224725/
More Top Deals from SPY
Best of SPY
