Footwear is a key component of your sailing foul weather gear, no matter what kind of sailing you intend to do. Sailing footwear’s primary function is to improve your grip on deck. It also serves to protect your feet from exposure to cold water, and the myriad toe-stubbing opportunities a sailboat provides.
Casual
Are you going out for a relaxing day sail with friends and family? Racing in a low-key evening series after work and don’t want to bring extra shoes? There is a wide variety of shoes that look stylish, and are better than regular sneakers on a boat. These shoes aren’t considered part of one’s sailing foul weather gear, rather they are fair weather gear.
The Original Sperry Top-Sider Moccasins are the average person’s idea of a boat shoe, and they aren’t a bad choice. The sole is of average grip, and the laces wrap around the heel for a secure fit when you’re hiking out. They are available in a wide variety of colors, solidifying them as the most stylish alternative. They don’t drain very well, and the leather will absorb water, so they aren’t a great choice if you expect to get wet. The sole also has very little cushion, which increases the tactile feedback on a boat, but walking around town they can quickly fatigue your feet.
For something with a bit more structure, the Columbia Boatdrainer II is a popular option. A much more comfortable sole than the Sperrys, and as the name suggests, they are designed to quickly drain water if they get dunked. They are a very lightweight, cushy shoe that is great for sailing in San Francisco Bay, because you want to get that cold water out of your shoe as quickly as possible!
Technical
If you’re on the foredeck, or doing some serious racing, Top-Siders aren’t going to cut it. You need a shoe with really grippy rubber, and that dries fast with a secure fit. The uppers will resemble regular running shoes, but they typically feature more mesh in their construction more maximum water-shedding, and the rubber often wraps over the toe for extra grip and protection if you’re working on your knees.
Helly Hansen’s Hydropower 4 deck shoe is a new style, with a quick-drying mesh and synthetic upper, and a grippy rubber sole. They have shock-cord laces and anti-microbial insoles to help keep the smell down.
Also in this category are dinghy boots, such as Zhik’s 260 High-Cut Soft Sole boots. These are constructed largely of neoprene, and work similarly to a wetsuit in that the small amount of water they retain is warmed by your body to help insulate you. They need to fit very snugly work well; Zhik’s side lacing ensures you have a tight fit while still enabling them to work with hiking straps.
Boots
All of footwear we have covered so far will increase your comfort on the boat, but they won’t keep your feet dry. That’s where sailing boots come in. They are waterproof, and sometimes breathable. If you’re sailing in cold, wet conditions for long periods of time, especially offshore, you’ll want a good pair of boots.
The Dubarry Ultima Stretch boots are the top-of-the-line choice, with water- and chafe-resistant leather uppers, and breathable GORE-TEX linings. If you’re going to be spending days or weeks at a time in them, this is the obvious choice.
At the other end of the spectrum are the West Marine Cruising Boots (available in tall or short). These are basic rubber boots: the soles are nicely grippy, and they are fully waterproof. They differ from the Dubarrys in that they aren’t breathable at all; they keep as much water in as they keep out, depending on how hard you’re working. Durability is also worse, with the rubber uppers prone to cracking at flex points. But they are dirt cheap, and if you are only doing occasional wet-weather sailing they are adequate. They are great if you’re cleaning the boat or doing other dirty jobs, as dirt hoses right off and the uppers can take a beating.
Landing in the middle are Sperry Top-Sider’s SeaRacer Boots. Less than half the cost of the Dubarrys, with arguably a grippier sole. The lining isn’t GORE-TEX, but still nicely breathable. You can find my more detailed review of them here.
Conclusion
Footwear is a critical part of your sailing foul weather gear. It’s sort of analogous to the tires on your car – every aspect of the car’s performance can be improved or hampered by the rubber, because it’s the only part of the car actually touching to road (ideally!).