There are number of high-quality boat shoes on the market, but not all are created equal. We ranked these shoes based on quality, durability, comfort and looks. And we kept things to just classic, brown leather — no canvas, no colors. It came down to this question: Can anyone really hold a flame to the classic Sperry Top-Sider?
If you’re looking for the best boat shoes for walking around that won’t wear out in a single summer, keep reading. Wear these to work with confidence. If you’re looking for the best shoes to wear on your racing catamaran, maybe head over here (and watch out for the auto-play).
Ready for this? Sit back, relax, put on some chill music, and enjoy!
The Golden Brown Maritime is a beautiful, hand-crafted shoe that will look great on the street and in the office (or on your wooden yacht). It’s a traditionally-sewn shoe made of very supple leather that your feet will love as it molds to them over time. With the quality of leather, the look of the shoe, and the comfort that AE is known for, the AE Maritime runs away with this one as our top pick as the best classic boat shoe available.
A step up in quality from the ubiquitous Authentic Original Sperry Top-Siders, the Gold Cup is the crème de la crème. The Sahara Leather Gold Cups are a steal at $106 at Nordstrom’s Anniversary Sale (more sale picks here), but you can find a larger color selection at Amazon for $159. These are similar to the regular Top-Sider but with hand-burnished premium leather and gold plated eyelets. Despite the silliness of gold-plated hardware on a shoe, the Gold Cup will hold up for longer than the original and look better through wear and tear. It’s a solid 2nd place pick at just $10 more than the original
This is a great shoe and the main rival to the Sperry Top-Sider. Interestingly enough, both Sperry and Sebago are owned by the same company as of 2012. They are slightly more comfortable than the AO Top-Sider (#5 below) and $35 cheaper. Their stitching makes the shoe look a little chunkier than the Sperry, but the lines are nearly the same from all angles. Unless you’re seeking a certain brand-name, the Sebago in brown/white is an easy pick at this price-point. Because of the price and the fit, the Sebago sneaks into 3rd place, and is our budget best-buy.
The classic look and feel of the Sperry Authentic Originals that you remember from growing up can still be found if you look hard enough! Sperry makes the classic AO (“Authentic Original”) specifically for J.Crew. This would have been the winner for old-times sake, except right now J.Crew has limited colors and styles available. We like the look better than the new AOs (next on our list), so if J.Crew still has your size, you should pick up a pair.
This is the 3rd Top-Sider in our top five. The Sperry Top-Sider has been the go-to boat shoe for years for both boating enthusiasts and people seeking that look. They are comfortable and they wear well. You can answer the question that always comes up when you’re wearing boat shoes, “Are those Sperry’s?” with a, “They sure are.” They’re a simple boat shoe made of good leather with refined stitching, an easy top-five pick.
It would be a great color of leather for a different style of shoe, but it’s not the golden brown we’re searching for. Timberland made the choice to move away from lighter colored leather (you can see it still available in limited sizes on Amazon). Timberland is known for their quality and their durability, so I wouldn’t blame you if you picked up a pair of these, but at this price point, you’re better off getting the much-better-looking Sebagos.
Someone has to lose. Inexpensive leather compared to our other competitors, as well as the poor design of putting a seam mid-foot, prevent this shoe from breaking in as well as a boat shoe should. Even if you’re looking for a disposable shoe, you might as well go for one of the cheaper and more comfortable canvas boat shoes on the market.
Bonus: Technically not the boat shoe style, but worth a look:
They have non-slip and non-marking soles which are the hallmark of a shoe made for boating, but with the two extra eyelets it’s a spin on the classic. This style of shoe is much better suited to someone that’s going to be putting some miles on their shoes and needs the extra lacing. Comfortable and sharp-looking, this would be a great pickup if you want a distinctive look in the boat-shoe realm.
So what do you think? Leave us your praises and other great boat shoe picks in the comments, and send all of your flames to localhost.