It All Started with Topsiders
When I was growing up boating back in the 1980’s my dad used to say that the only real deck shoe was the “Topsider.” He would cringe if I showed up to the boat with sneakers and would require that I change into top-siders before boarding. According to him, because of the specialized sole and tread of the topsiders, it was the only shoe that he thought suitable to use on a boat. Anything else, and you would surely slip off the boat and die. Dramatic, huh?
Anything else, and you would surely slip off the boat and die.
To an extent, he was right. While I’m sure there were plenty of suitable sneakers that would have got the job done safely, he preferred to eliminate the guesswork and go with what he knew works. Props to him for that. The only problem: Man they were hideous! They had sort of a duck-bill shape, a little square heel at the back and those stupid leather laces that would eventually rot and break. They offered little support and if you ever got them wet they would turn solid and you would never be able to flex your foot in them again! Plus, my dad, with his long khaki slacks could pull them off well. But a 10-year-old kid in colorful shorts and white sneaker socks certainly could not! These days I don’t own a pair of topsiders. I happily race in both bay and ocean regattas wearing good ol’ skater Vans and I’ve yet to fall overboard once (or slip and smash into what my son calls the butt-bone). But the point I’m trying to make is that no longer are you confined to the standard old topsiders since even Sperry learned a thing or two about making fashionable sailing shoes. Plus, to avoid the problem of hardened leather you have plenty of good options for materials. You can still get leather if that’s what you fancy, but there are plenty of options available for suede, denim and canvas deck shoes. Plus, you are no longer confined to the shoe in the traditional sense of the word. Performance sandals, or “sandal-hybrids” as I like to call them such as Teva and the increasingly popular Keen brand, are now being more widely accepted on boats. I say this using the traditional, conservative, older sailor as a point of reference. Some will still kick you off the boat if they see you in sandals.

Sperry can still pull off the traditional duckbill look with some modern changes though. They call the most traditional looking model “The Original Boat Shoe” while also opting for adding a modern twist to the shape. One such example of the more modernized ones Sperry calls the “Billfish.” Good thing, cause that sounds a lot better than my description of duckbill! Guess what? The originals still carry the square-ish shaped leather laces and side trim, but I guess they wouldn’t look very original othewise. One day I’ll be an old sailor too and I might want a pair of those traditional shoes again. Sperry is still the biggest maker of marine shoes (or so it seems at least) and they are obviously good and reputable. Additionally, at some point they figured that not everybody liked the standard leather boat shoes and they went ahead and designed some boating sneakers. They even made ones that look just like classic Vans slip-ons! Good thinking Sperry! A quick web search even returned some Sperries (can I say it like that?) made with what looks like gator skin. Perfect if you pay for your boat by being the lead singer of a latin Salsa band.
As you can see, there are options galore by Sperry, for everyone… However, let’s look at a couple of other options…
Losing the Leather – Canvas Deck Shoes
The other option I’m talking about revolves around other brands taking a proven design and proven materials to create their very own boat shoe. Of all these new emerging styles, canvas boat shoes are hugely popular. Canvas has a number of benefits over leather. First, canvas is less expensive, very durable, and does not deform like a dead cat in the sun the way leather does when it gets really wet. You can get them wet and dry them again a multitude of times without having much problems. A number of major brands saw the financial opportunity of making deck shoes and they jumped aboard too. [Shaking head at the pun]. While some are genuine sailing brands that are dedicated to real sailing shoes, some are not.

Some sailing and non-sailing brands making deck shoes are:
- Lacoste
- Polo Ralph Lauren
- Timberland
- Sebago
- Durham
- Dubarry
- Rockport
- Patagonia
Now, like I said above, some of these brands make real, genuine boat shoes. Others are in it only for the style. So, don’t blame me if you choose incorrectly, slip and break your butt-bone. If you are going purely for style when around town, by all means take your pick. But if you want real performing sailing shoes make sure that you check to make sure the ones you are buying are designed for real boat decks, not barbecuing decks. And don’t just take the salesperson’s word for it. He’ll tell you they are good for running a marathon if that’s what you’re looking for, just to sell you.
There is one company I love to buy my sailing shoes from… And yes, they also have the original top-sider! That would be Zappos. Their entire array of boat shoes is available for purchase here.