When it comes to seaworthy style, Sperry boat shoes are the most recognizable loafer, combining form and function. But it’s their comfort that is most remarkable.
With genuine leather materials hand-sewn for durability, a signature 360° lacing system with rustproof eyelets for a secure fit, and razor-cut wave-sipping soles for the ultimate wet/dry traction, the Authentic Original 2-Eye Boat Shoe from Sperry hits it out of the park in terms of construction, comfort, and style. Definitely, one of the best boat shoes you can find.
It features moccasin construction with OrthoLite insoles for enhanced shock absorption and comfort as well as a shock-absorbing EVA heel cup. There has been some discussion about a new production of Sperry boat shoes, one that relies more on automation than handwork. We’ve found it hard to validate.
Either way, just remember that a Sperry shoe will often stretch a wee bit, so don’t order big.
Whether you’re on your first boat shoe, or in the market for a new one, if you’re remotely active in boating, you’ve likely heard of Sperry’s iconic Men’s Authentic Original 2-Eye Boat Shoe (otherwise known as the Authentic Original, or A/O)—the boat shoe that started it all.
Originally intended for rugged, seaworthy sailors, the A/O has since morphed into a summer staple that’s used more on college campuses and other casual settings than on an actual boat.
While a number of brands have come up with their own boat shoes (all of which claim to have improved upon the original), Sperry’s A/O boat shoe is still one of the top-selling models on the market today.
Is it still the standard against which all other boat shoes are measured? Is it overhyped? We tested the iconic A/Os to find out.
Sperry Shoes Are Originals
The Sperry Men’s Authentic Original’s’ design, as is the case with most leather-clad, moccasin style boat shoes, is geared more towards casual summer wear (or if you live in the tropics, casual everyday wear) than anything else.
Their hand-sewn Tru-Moc, full-leather construction makes them a more stylish alternative to canvas sneakers or your regular walking shoes. Paired with a casual button-down shirt, the right-colored pair of pants/shorts, and some nice sunglasses, you’ve got a nice, slightly dressed-up summer look!
Obviously, this isn’t to say that the A/Os are horrible on deck. Not at all. On the contrary, they’re quite good for sailing and for days when you just want to hang out at the beach.
They’re lightweight, flexible, and quite easy to get in and out of when you’re near the water. Moreover, their non-marking rubber soles offer a respectable amount of traction on deck.
While they’ve definitely changed over the years, the A/Os don’t really offer much in the way of innovation. As of this writing, it appears Sperry is confident with their original boat shoe, and as such, prefers the if-it-ain’t-broke-don’t-fix-it approach.
Sperry’s Boat Shoe Comfort
When it comes to comfort, Sperry boat shoes are a bit of a hit or miss. Although they’re available in wide sizes, they’re notorious for running a little narrow.
While the leather construction keeps your feet cool, depending on how wide your feet are and/or how patient you are, breaking in the leather for a comfortable fit can be a bit of a chore (and can result in more than a few blisters!).
Moreover, while their Ortholite® cushioning offers support, their mostly flat soles aren’t meant for rough terrain or lengthy hikes. If you find yourself on a rocky beach or walking on unpaved roads on your way to a nice beach, you will feel every sharp rock and every uneven spot.
That said, once the shoes are well broken in, they’re quite comfortable in casual settings, like when you’re lounging in, say, your favorite coffee shop, on your yacht, or in a library.
Use
What’s great about the Sperry A/O is that despite the stigma attached to it of being a vital part of a trust fund baby’s wardrobe, it’s actually a relatively versatile piece of equipment.
While it’s mostly relegated to casual, everyday use (as we’d wager most A/O wearers don’t really go sailing, much less have a boat for sailing), it does hold up fairly well on deck.
While not offering the best traction among its peers, its non-marking rubber sole with its signature Sperry Razor-Cut Wave-Siping™ gives it a fair amount of grip on wet surfaces.
Moreover, its leather upper does develop a nice patina with daily use, especially when constantly exposed to water.
That said, it doesn’t offer a lot of support, and it’s definitely not a performance boat shoe by any stretch.
Moreover, to prevent the leather from cracking or wearing out quickly, the shoes have to be carefully cleaned, air-dried and lathered with leather conditioner and leather polish every time they get soaked.
You’re better off with Sperry’s Men’s ASV Shock Boat Shoe, or their Sea Kite Sport Moc if you want something you can use exclusively for sailing and/or other intense water activities.
For lazy summer afternoons by the beach, or casual meetings with your startup’s investors, though, the A/Os should be right as rain.
Material
The Sperry A/Os feature a full-grain leather upper, with a classic, moccasin design. While not as breathable as boat shoes that feature a full mesh upper, the leather construction does make up for this by being quite pliable, ensuring a snug yet comfortable fit.
The shoes also feature rust-resistant eyelets, which are great for all sorts of casual water activities. The A/Os also feature Ortholite insoles for added cushioning and comfort.
Lastly, the shoes have the tried and tested non-marking rubber wave-siped outsoles that allow for more traction on wet and dry surfaces.
That said, while the A/Os have remained virtually unchanged in terms of its overall look, the quality of the leather as well as the stitching used for these iconic boat shoes seem to have declined a bit.
Then again, if you only use the A/Os as they are intended to be used (for casual settings), and as long as you take proper care of them and store them properly, you should be able to wear them for many summers.
Value
While the overall quality has declined a little bit over the years, the A/Os remain a classic pair that’s still a solid choice for those who want a serviceable boat shoe that can go well in all sorts of casual settings.
Sperrys are the most popular boat shoe by search data, according to our research, but these ones are very similar to the Timberland Men’s Classic and Sebagos. These are all great footwear and similarly priced. Ralph Lauren’s Merton shoes also have the classic look, but are more expensive–and slightly better built.
Either way, you won’t feel out of place when using these for seaside strolls and casual boating. They do have quite a good grip for what they are, and they’re easy to get in and out of if you have to go barefoot to tackle extremely slippery terrain.
That said, the A/Os true place is in more confined, relaxed places, where the most strenuous activity you’ll be involved in is either getting your check and/or shifting in your seat.
Moreover, while they’re lightweight and comfortable enough, they’re definitely not for people suffering from any foot condition or heel pain. They have a mostly flat rubber outsole that doesn’t really offer much support.
All in all, the Sperry Men’s Authentic Original 2-Eye Boat Shoes isn’t the best pair of boat shoes in its segment. However, it’s still a versatile pair of boat shoes that can go toe to toe with its slightly better counterparts when it comes to style.
If you’re looking for a timeless pair of leather boat shoes, you won’t be wrong for choosing the A/Os over its peers.
