
Recently, I was digging through my file of “less than optimal boating decisions,” a collection of errors made during decades of boating, and which I prefer to avoid repeating. In the assemblage, I found half of what was once a pair of Cole Haan slip-on dress loafers. Having served their intended work purpose, they were relegated to yard work and various outdoor activities, and somehow ended up adorning my feet while I was at sea.
For reasons still unclear, I left the house in them for a day of crabbing aboard a nice, mid-20-foot sportfisherman. The crabbing was a great success; the choice in footwear was not.
I ended up entering the water a bit while launching the boat. (First mental note: Wet leather dress shoes do not dry quickly.) At various points in setting and pulling the pots, my footwear had an uncanny—but, in hindsight, predictable—ability to fall off. (Second mental note: Slip-on shoes may not stay on.) We ended up taking a few crabs ashore for an impromptu crab feed, which led to another water landing for the shoes, and some sand and rock infiltration. And, when we were back at the marina nearing dusk, while loading the boat back onto the trailer, one shoe slingshotted off my foot and flipped over the side of the dock. (Third mental note: Shoes work best when you have one for each foot.)
I returned home, and my wife was happy with the crabbing success, but duly asked, “How do you lose a shoe while boating?”
And so it came to be that my choice of footwear ended up in the file.
Appropriate seagoing footwear is important. Fashion may be first on a boater’s mind when selecting boating footwear. I think the more important consideration is safety, but it’s possible to have both.
Good boating footwear should fasten securely to the feet, to avoid the drink. It should have traction for wet and slippery deck surfaces. It should be water-resistant, waterproof or constructed of fast-drying materials. It should provide a level of warmth appropriate for the weather. And it should be comfortable.
If your deck shoes no longer meet these requirements (or maybe never did), it is time to consider new footwear.
The nonslip surface on many boats is there for a good reason, but it can tear up bare feet with some degree of unpleasantness. Good footwear not only protects the feet, but also matches up with the nonslip to maximize its benefits.
Do you like cleaning black rubber marks from the deck? Probably not. Another quality found in good boating footwear is nonmarking soles.
And if you’re the captain, you probably do not want to be distracted by what’s on, or not on your feet. The same goes for guests who double as a first or second mate.
Although there are many great manufacturers of serviceable boat shoes, and it is possible to have just one set of footwear aboard, I tend to allocate the footwear duty to a few different sets.

City Shoes
These are the shoes we wear on land. When I arrive at my boat, the city shoes come off and are stowed until I return home. City shoes are rarely a good option for boating. (Though I have kicked some ice on the dock with dress shoes. Who hasn’t?) I try to avoid using good boat shoes on land, as I don’t like tracking dirt, sand and other debris onto the boat. Conversely, while I love the smell of the sea, it’s sometimes best to leave the odor of seaweed and salt air out of the office meeting.
Cruising Shoes
These are the workhorses of my boating shoe lineup, meeting all the requirements for good boating shoes. I wear these around the dock, while working on the boat and, of course, while cruising.
Water Shoes
Back in my youth during the ’ 70s and early ’ 80s, water shoes were basically any old pair of athletic shoes that I’d wear in the water to protect my feet from rocks and barnacles. Fortunately, water shoes have come a long way since then. These are shoes specifically designed for water immersion, and to shed water quickly. I like having a pair on board mainly for when I am on the beach, or for when I go out in the dinghy fishing, crabbing or just roaming.
Go-To-Shore Shoes
This might be a pair of shoes for when you find yourself at a nice shoreside restaurant, or meandering through a quaint seaside town. For some, these shoes may have a heightened degree of fashion, though in my case, the go-to-shore shoes are usually a newer (and cleaner) version of my cruising shoes, thusly available for double duty later in their functional life.
Apres Cruise Shoes
What about the ubiquitous flip-flips, slides or sandals? Leave these for a single purpose: cocktail hour. I would need many more than 10 fingers to count the number of lone flip-flops I have found floating around. Maybe the owner was boarding the dinghy to return from shore, one foot got stuck in some mud or sand, the flip-flop came off and it was just left behind. Maybe the flip-flop wearer was scrambling about the deck preparing to dock, and in the process of tossing fenders over the side and moving from stem to stern, a line caught the flip-flop and sent it into the drink.
Flip-flops can also be dangerous, often leaving much of the foot exposed and unprotected, and sometimes lacking in good traction. They do not normally meet any of the requirements for suitable cruising footwear.
So, there we have it. Happiness is, in fact, in the sole.
Douglas M. Wartelle is a Pacific Northwest native with 40 years of boating experience in the waters of Puget Sound, the San Juan Islands and the Canadian Gulf Islands. An attorney in Everett, Wash., by day, when he’s not in the office he can often be found on the water or, in the off-season, planning his next boating adventure.
This article was originally published in the May/June 2022 issue.