Sailing Shoe Reviews

[Prairie Schooner]

For twenty years I've raced on friends' boats at least two nights a week. As many note, the soles get hard and slick much more quickly than I'd like. Thus, I plan on replacing my shoes every two years. These are my last five years supply.


Merrell Trail Glove 5. Really great shoes, functionally. Great grip, supportive, comfortable. Weird styling. $65 in 2021.


Whitin Trail Running, Chinese OEM on Amazon. Excellent grip, still holding quite well. Not enough support, more like barefoot. My feet hurt after a few hours standing on them. Note, I wear orthotics in some of my street shoes. I don't like the absence of a toe guard. The soft mesh body coupled with the stiff arch panel hurts across my arch. But fantastic grip. $44 in 2023. Because of the negatives I decided to get another pair of Merrells.


Merrell Trail Glove 6. New design. Absolutely awful shoes. Grip not nearly as good as the TG 5. The mesh body started to unravel after only a few weeks of use. About a quarter size too small. Good support. $84 in 2024.

I've had legit sailing shoes before, I remember some Sperrys that were pretty good. Sperry, Helly, Zhik, Musto, all charge so much for them, I'm kind of on a quest find a less expensive alternative. I still rebel at paying more than a hundred bucks for a pair of shoes. I'd buy some more Trail Glove 5s, but they're discontinued and I worry that the sole material hardens with age so even new-in-box wouldn't be so good because they've been on the shelf for a while.

 

[Loren Beach]

An unlikely choice, perhaps, but I have been using my Keen Targhee 3,
walking shoes for deck shoes for years. Works well, with great traction. Not very "yachty", admittedly...
Waterproof, too.

 

[Vtonian]

Look for Sperrys on Black Friday (and everything else on your wish list). In the winter, nothing but XtraTuf on my feet for all boating. A little too narrow for my feet but very flexible and to have warm and dry feet in even 40deg blowing rain is worth it. Costco merino wool socks too.

 

[bsangs]

Merrell was my go-to for hiking for many years and then something changed. The quality, the fit, the traction - all went into the dumpster. So never even tried them for sailing.

Sperry, Columbia and Astral have served our sailing feet well.

 

[AdventurousAnton]

I've been sailing with Sperry shoes on my feet since the early 80s, and that hasn't changed. My current fave for sailing is Sperry's SeaCycled Headsail Sneaker. Comfort, stability, super-grippy soles...what more could a sailor ask for? I always catch them on sale, as well, making them pretty darned affordable.

 

[Bepi]

I did a review of the Dansko slip-on shoe a few years ago and I stand by it. I spent most of my life wearing Topsiders like a second skin but the quality declined and I was going through a pair in less than a year. The Danskos are designed for professionals like nurses who spend lots of time on their feet and the non-slip is fantastic. They are durable and last a long time. This past weekend I landed the canoe at Italian Gardens on Catalina and waded in the surf, then a hike. A freshwater rinse, a dry, and a bit of polish and they are good to go. And though they are slip-on I could sprint in them without fear of them flying off. The soles will not leave marks on your deck. Thick leather, yet light, after 4 days of sailing and hiking the only thing that doesn't hurt on my body is my feet. This link merely is to show the model, they can be purchased anywhere. All I can say is if you have any concerns about what's on your feet, end them by buying these shoes.

Dansko WAYNE Black Leather Slip-On Shoes

The men's Dansko Wayne in black ships out for free at Family Footwear. Featuring a slip-on design with a slip resistant outsole. It's a comfort dress shoe that's easy to get on.

www.familyfootwearcenter.com

 

[gabriel]

I prefer leather. I find that leather upper top siders become perfectly supple once they absorb a little saltwater, and they dont stink up when worn sock-less (which my wife appreciates). Mine are a few years old and the quality seems great.

 

[peaman]

I also like the aesthetic of “traditional” leather boat shoes. I am currently on my fifth pair of Sebago “Schooner” shoes over the past thirty years. The two eyelet lacing over the single layer tongue of the Topsiders were a pain for me, but the padded tongue of the Schooner is comfortable. And when not too old, they look more dressy than Topsiders, but still salty. When the soles lose their grip, it’s time for a new pair.

 

[Christian Williams]

When the soles lose their grip, it’s time for a new pair.

Mine do that in a year. I think older boat shoes should be relegated to washing the car. When working on a pitching wet deck, especially when something has gone wrong, a reliable grip makes the difference.

I notice a return to barefoot on traditional boats, or maybe it's just Tally Ho. Lunacy. Stubbing a toe on a cleat can mean disabled for days.

 

[AdventurousAnton]

I notice a return to barefoot on traditional boats, or maybe it's just Tally Ho. Lunacy. Stubbing a toe on a cleat can mean disabled for days.

100% in agreement, because no matter how situationally aware I am, I run into my foredeck fairlead...always.

 

[bigd14]

Stubbing a toe on a cleat can mean disabled for days.

The few times I have dared to walk barefoot in the boat I have paid a terrible price. No more. The requisite blood sacrifice exacted each visit is enough.

 

[Gaviate]

Hmmmm, I'm one of those barefoot guys, but I also live my life ashore wearing only flip flops...work or play.
Now we are approaching boot season, (cold) where my toes get numb when its 40 degrees or lower. If I keep the boat in the water for some November sailing, I'll have to wear my insulated winter boots!
Only 5(ish) months till flip flop season is here again!

 

[Prairie Schooner]

When I was teaching college there were always those interesting in-between periods when on the same day some kids (er, students) were wearing flip-flops and others wearing Uggs. When folks come sailing with us my dictate is that there are no bare feet, no open toe sandals, God forbid flip-flops. Preferably good grip sneakers. But, @Gaviate , go for it! Your boat, Your rules. Freedom of the open seas. ‍

 

[Slick470]

When casually sailing by myself I'm often barefoot, but I can't count the times that I've kicked a cleat or other bit of deck hardware and wished I'd been wearing shoes. When racing I always wear shoes, usually moving quick enough around the boat to not want to chance it, plus with crew, the likelihood of getting stepped on goes way up.

My favorite sailing shoes so far have been the Adidas Terrex boat shoes. However, like most things that I discover and would buy over and over again, they don't make them anymore. I've been babying the pair I currently have. Not sure what I'll get next.

 

[Prairie Schooner]

When casually sailing by myself I'm often barefoot, but I can't count the times that I've kicked a cleat or other bit of deck hardware and wished I'd been wearing shoes. When racing I always wear shoes, usually moving quick enough around the boat to not want to chance it, plus with crew, the likelihood of getting stepped on goes way up.

My favorite sailing shoes so far have been the Adidas Terrex boat shoes. However, like most things that I discover and would buy over and over again, they don't make them anymore. I've been babying the pair I currently have. Not sure what I'll get next.

Terrex, YES!! I forgot about those. I had two pair in succession. They were great boat shoes. Nigh on perfect. Reasonably priced. And, as you say, discontinued, alas.
edit: Out of curiosity, I searched and they retain the name but the shoes seem quite different. The pairs I had looked more like this-

 

[Slick470]

Terrex, YES!! I forgot about those. I had two pair in succession. They were great boat shoes. Nigh on perfect. Reasonably priced. And, as you say, discontinued, alas.
edit: Out of curiosity, I searched and they retain the name but the shoes seem quite different. The pairs I had looked more like this-
View attachment 51192

That is what mine look like, different colors, but same design. I love those shoes.

Adidas still sells Terrex shoes, but I think they call anything that isn't specifically for a sport and more outdoor focused as Terrex, so lots of different options there for trail running, hiking, approach shoes, etc. For the boat shoes, I can find what may be a later design but only in odd sizes. My guess is they are the last of the stock. I wish I had bought a couple extra pairs...

 

[Christian Williams]

Sperry Gold Cup Mako. To reproduce 1965 this is as close as I can get. About $100. Leather, takes a day to dry, Topsider soles get hard in a year. There is enough sole padding for comfort (unlike originals, which had zero). Cannot possibly recommend, only report many years of shrug. They do last a long time once rejected from boat use.

 

[bgary]

Hmmmm, I'm one of those barefoot guys, but I also live my life ashore wearing only flip flops...work or play.

Ditto.

On the boat I'm generally barefoot or in flip-flops. But then I'm generally day-sailing and - these days - my idiom is that it's not sailing weather unless I can go in shorts and flip-flops. Neatly tautological, huh?

Cold-and-wet weather, I have a decent pair of boots that quite-stylishly color-coordinate with my Helly Hansen salopettes and smock.

In between... my favored deck-shoe depends on what I'm doing. If racing on OPBs, I've got a pair of Sperry sneaker-style shoes that are good and sticky. I only use them racing so hopefully they'll last for a while. I got them on a 50%-off sale at West Marine, kinda wondered if they were worth even that but they've performed quite well so far.

Men's Harbormaster Shoes | West Marine

Check out our Men's Harbormaster Shoes and more from West Marine!

www.westmarine.com

For more casual purposes, I lately favor the Reef "neptune".... good protection, super-comfortable with or without socks, styled somewhat like the old sperry canvas deck-shoes, with the addition of a clever fold-down flap at the heel that allows you to wear as a slip-on.

Swellsole Neptune

Your all day, every day, go anywhere shoe is here. Classic styling comes to the unmatched comfort and ease that is REEF’s hallmark. The SWELLsole Neptune takes you anywhere, from slipping on with the crush-back heel for morning coffee runs to go-with-everything styling for a casual night out...

www.reef.com

Olukai makes a similar model, but nearly twice the price and (IMO) not twice the value.

Moku Pae Men's Boat Shoes - Trench Blue / Off White | OluKai

Shop the Moku Pae Men's Breathable Boat Shoes - Trench Blue / Off White at Olukai.com! Premium, Handcrafted, Hawaiian-inspired Men’s Water Ready Shoes. Free Shipping. Free Returns.

olukai.com

Oh, and yeah, I still have a pair of leather Sperry's for those dress-up occasions at "the club". Last saw the light of day a year ago when attending a friend's induction into the National Sailing Hall of Fame. So it goes.

$.02

 

[Bolo]

I have the unfortunate curse of being born with bad feet, notably very bad bunions inherited from my mom via genetics. This has caused me, over time, to develop a foot neuroma which when it acts up is like standing on a lit charcoal briquette. So, buying shoes, any type of shoe is a challenge because I need extra, extra wide shoes (along with special inserts provided by my podiatrist for an exorbitant amount of money) to have any sort of comfort. Buying the typical boat shoe is out of the question, they don’t sell shoes wide enough. So I need to buy on line from companies like Apex or Merrell. Currently wear Merrell for sailing and I found them comfortable and “grippy”. I also sail in sandals which I know is almost like sailing barefoot (which I also sometimes do) and, yes, sometimes I pay the price for it by taking a hit on my bunions and that’s when I do curse like a sailor.

 

[bigd14]

Many "youth" today love Crocs and may want to wear them aboard. I thought they might be a good solution, but I found them ill-suited for sailing. I had a cleat get jammed through one of the holes in the toebox which peeled the shoe (if it can be called that) right off, flipped it overboard, and bruised my foot. They are also very unstable and sloppy especially when your feet get wet. They do float high and dry instantly which is useful (I was able to retrieve the errant Croc), but I now only use them carefully for washing the deck.

NOT recommended!