Dave and I each only have three pairs of shoes. Here's what we have and why they work for us.

Three Pairs of Shoes

Once upon a time, I had lots of shoes. Lots and lots of shoes. Dress shoes. Business heels. Casual shoes. Beach shoes. Winter boots. And so on . . .

Since 2002, just after we moved onto Que Tal, I’ve only had three pairs of shoes at any one time. Okay, I also have a pair of sailing boots that double as fin booties. So maybe you could say I have four pairs. Ditto for Dave.

But I do get asked about what shoes I/we have and what do I recommend, so here goes:

Keen sandals. I’ve worn Keen sandals since 2005 for about 95% of what I do. Obviously I love them. So most of this post is about why they work so well for boat life.

Up until the very last pair that I bought, I always wore the Newport H2; my latest pair is the Whisper model. Dave also wears the Newport H2’s. These are the Newport H2’s:

Dave and I each only have three pairs of shoes. Here's what we have and why they work for us.

All of the models with “H2” are designed to go in and out of the water (perfect for wading to/from the dinghy, walking on the beach, etc.); several other models such as the Whisper are as well. They don’t stretch out when wet, get moldy or create blisters when worn wet on a hike. They’re great when wading in places without a nice sandy bottom.

Almost all Keen sandals are what are called “hiking sandals” meaning that they have the support needed for all but the most rugged hiking — and we certainly put them to the test while cruising the Sea of Cortez. The soles are thick and thorn-resistent — a quality I came to value after taking a simple walk in Baja with Crocs. Pretty much every single one of those thorns came right through the sole.

Dave and I each only have three pairs of shoes. Here's what we have and why they work for us.

One of the best features about most Keen models is the toe guard — it really prevents a lot of tripping incidents and toe injuries. Admittedly, it’s harder to shake a small pebble or bit of gravel out of the sandals, but overall that’s less of a problem than the toe injuries (and thorns I kicked) with my previous Tevas. Because of the toe guard, I was even able to wear them while hiking over a lava field in Hawaii: Keens are the only brand of sandals that the guide company will let you wear; otherwise you have to wear sneakers or hiking boots.

Back in 2004/5, several cruising friends recommended the Keen Newport H2’s to me after that thorn incident with the Crocs, but I resisted for over a year due to the cost. Nearly $100 for a pair of sandals??!!? I finally broke down and bought a pair when I realized that the cheapies only lasted a few weeks with the abuse I gave them (shoes today, it seems, generally aren’t designed for people who walk just about everywhere). I’ve decided that Keens actually are a good deal: a pair lasts me 6 to 9 months of pretty much constant wear and then becomes my paint shoes!

One thing that I particularly like is what I can “field repairability.” If anything in the sandal fails, it tends to be the stiching that holds the woven fabric (almost webbing) to the neoprene lining, and the shoes get loose — but not unwearable. A bit of dental floss or sail thread and a needle, and they’re good as new again.

I’ve never had the shock cord lacing break, but if it did it could be tied back together . . . and we always have spare shock cord on board if we needed to replace it. The repairability was critical when we were in the Sea of Cortez, Mexico and there were no shoe stores nearby . . . and the ones in the bigger towns only carried “dressy” sandals for women, not walking sandals. Other sandals that tend to fail when the uppers pull out of the sole are not nearly as easy to repair.

TIP: If you’re going to be cruising Mexico, take several spare pairs of sandals with you. Women’s “recreational” sandals (Tevas, Keens, etc.) are almost impossible to find, and it’s hard to find men’s sandals in sizes over about a US 9.

About 2 months ago, I bought a pair of the Whisper model because I didn’t like the colors then available in the Newport H2’s for women. I like the Whispers even better — they aren’t as heavy or as clunky looking, and seem to be giving me every bit as much support and toe protection. They have the same great non-slip sole as the Newport H2’s, too. While the soles are black, they’ve never marked a boat I’ve been on.

Here’s what the Whispers look like:

Dave and I each only have three pairs of shoes. Here's what we have and why they work for us.

It used to be that you could find Keens online for 25 to 30% less than in stores, but that’s pretty much gone away now — although if you wear an odd size or are willing to live with an unusual color, you may find a pair at 10% off. I buy mine from Amazon due to the huge color/size selection:

Sneakers/Running Shoes. Occasionally, it gets cold where I am. Usually, that means that I put on a pair of socks with my Keens. But occasionally I need something more. So I get out my sneakers. If it’s that cold, I’m usually wearing jeans, so they fit right in.

Once in a while, I even wear my sneakers for a hike or long walk, but it’s pretty rare since I discovered Keens with the toe guards.

Dave’s second pair of shoes is also his running shoes; he wears them about as often as I do.

If you’re going to leave your sneakers on the boat full-time, don’t make the mistake I did when we first began cruising on Que Tal. If there is any real leather on your shoes, it will mold and then disintegrate. Only buy shoes with no real leather!

Dress Shoes. I wear dressy shoes maybe four or five times a year — most of our socializing is very casual.

For me, a pair of somewhat dressy sandals in a neutral color and style works for all occasions. I keep the heels low — after wearing flats most of the time, high heels are dangerous for me . . . and frankly, I’m not about to wear hose!

Here too, the no real leather rule applies. My current dress sandals are wide black elastic bands with low heels, chosen for their ability to go with just about anything. Espadrilles in a neutral color also work well.

A far cry from the days where I had a dozen pairs of pumps, each specially matched to certain outfits!

Dave wears dress shoes about as often as I do. He doesn’t have a suit on the boat, so “dress” shoes means something to go with nice slacks. He has a much harder time finding something appropriate without real leather than I do. Several years ago, he found a pair that are styled similarly to TopSiders, but made with synthetic leather. They work.

Bottom Line. Neither of our cruising boats have been particularly large, and what space we do have we’d rather use for things like spare parts, tools and maybe a bottle of wine. We’d rather spend our money on those, too.

When we first started cruising on Que Tal, we both way overestimated how many pairs of shoes (and how much clothing) we needed. Within just a few months, we’d both cut back to just three pairs. I was shocked to discover that I didn’t miss having more!

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  • Lupari Sue
    Posted at 25 June 2015 Reply

    Will have to look into keens. I am not terribly fond of the look but they seem sound. My husband has bought a pair.

    • Lynn Kaak
      Posted at 25 June 2015 Reply

      When you go for Keens, don’t get the aggressive hiking sole. It has a horrible tendency to delaminate, and they aren’t easy to glue back together. Get the soles that are one piece.
      And they have some “cuter” ones, too.

  • Iain Fraser
    Posted at 25 June 2015 Reply

    Kate Courtney 😉 lol xxx

  • Dave Skolnick
    Posted at 25 June 2015 Reply

    No sailing boots?

    • Bill Dixon
      Posted at 25 June 2015 Reply

      Glad you recommended Keens. Love mine. No more crocs for me.

    • The Boat Galley
      Posted at 25 June 2015 Reply

      They double as my fin booties (neeoprene) and I’ll admit, maybe they’re a fourth pair. :/ I wear much more often for snorkeling than while sailing — where we are, it’s rare that we need them on deck.

  • Darlene Burnett Price
    Posted at 25 June 2015 Reply

    I also need a pair of 3″ wedges so I can see over the dodger to steer. Note profile picture peeking over the dodger.

  • Mary Facker
    Posted at 25 June 2015 Reply

    Yes, I really think you just need three types. Land, water, and boat. This past week I used a pair of Vibrams for my land to beach shoes, and after kayaking 2 miles I stepped onto land and the soles fell right off! I will be looking into the keens as a replacement.

  • Ron Dionne
    Posted at 25 June 2015 Reply

    I’ve had the same pair of Keens for 6 years with one minor repair to sole with super glue. I love em…

  • Helen Kitchen
    Posted at 25 June 2015 Reply

    Do the Keens smell really bad after being in salt water? This drives me crazy…sure you can rinse shore shoes in fresh water, but if you have a limited supply you can’t do that every time you go ashore.

    • Carolyn Shearlock
      Posted at 25 June 2015 Reply

      I almost never rinse mine (only if, say, I’ve been playing in mud) and I don’t notice a smell at all. In and out of salt water almost daily.

      • Helen Kitchen
        Posted at 25 June 2015 Reply

        Thanks Carolyn…it is a bother…will try them out…perhaps they don’t absorb the water!!
        We cruised Mexico and on to the South Pacific with our kids for 3 years..we wore flip-flops and replaced them when we could! We live on the East Coast of Vancouver Island now …retired with kids grown…grand kids…and they have boats…go figure where they got that idea!
        Cheers, enjoy reading your column…I have bought a “stove-top oven” and am about to try it out this coming week…we have gone to “the dark side” and have a Tiara 31 with no oven. I used to make pressure cooker bread when we were offshore, but am going to try the oven as suggested on your website!

  • Bruce (s/v Migration)
    Posted at 25 June 2015 Reply

    I’ve heard great things about Keens for years and have tried them several times. They just don’t fit my feet so I’m still wearing my Chacos which are fantastic sandals. No toe guard but the most comfortable sandals I’ve ever worn. And the company is terrific. Excellent warranty and customer service.

    I even wore my Chacos (by mistake) climbing Pacaya volcano in Guatamala. The bottom of my wife’s sneakers melted but my Chacos were fine.

  • Joanne Smith
    Posted at 25 June 2015 Reply

    My first pair of Keens only lasted about a month. I carelessly left them where our Lab pup could find them. My second pair I bought in 2005 and just replaced them. They are still in good shape but I wanted a new pair for work. I’m a nurse and work 12 hour shifts. They are some of the most comfortable shoes I’ve had.

  • Petra Obbes
    Posted at 25 June 2015 Reply

    Not just in case, ’cause you’re a girl and you want to wear them (no, not on deck)!

  • Iain Fraser
    Posted at 25 June 2015 Reply

    Yes dear! 😉

  • Candy Ann Williams
    Posted at 25 June 2015 Reply

    I only have 3 pairs too! Lol

  • Jeff Janacek
    Posted at 26 June 2015 Reply

    No Crocs? You’ve got to be kidding.

  • Victoria Horner
    Posted at 26 June 2015 Reply

    Not possible

  • Cheryl
    Posted at 26 June 2015 Reply

    I was doing some reading that said not to wear your land shoes on the boat and vice versa?
    Do you keep the keen for land? If so, what makes a good non marking boat shoe? Just wondering what people do. Also, assuming boat boots are like rain boots for rainy weather? Also what are fin boots? Thanks!

    • Carolyn Shearlock
      Posted at 26 June 2015 Reply

      I’m barefoot more than not on the boat — remember, you’re at anchor or at a marina most of the time. Other than that, I wear the same shoes (Keens or sneakers) on land and on the boat. Not quite sure why they said not to, unless it’s for not getting sand and dirt on the boat.

      Some shoes, particularly with soft soles, will leave black marks on non-skid. I don’t really know of a way to tell in advance, other than seeing if they are advertised as “non-marking” or someone else telling you that a particular model hasn’t left marks for them.

      Fin boots are the liner booties that you wear with snorkeling/dive fins — some fins are made with an enclosure for your foot while others have just a heel strap. If you have the type with a heel strap (typically a larger dive fin, which is what we like), you have to wear a bootie.

      • Cheryl Buckner
        Posted at 26 June 2015 Reply

        Thanks! Maybe it was for the dirt? Taking some lessons this summer on our reservoir and am just doing some reading. Lots to learn 🙂

  • Linda Kloepfer
    Posted at 28 June 2015 Reply

    Hi there! Love your info & generocity in sharing. I am wondering what you are doing for health insurance since you are not retirement age. My husband is on Medicare. I am 63 and want to retire also but not sure what to do for health ins or where to find it. Websites are so confusing. Thanks! Not sure this is where I should be posting this question!!

    • Carolyn Shearlock
      Posted at 28 June 2015 Reply

      My husband is on Medicare. I have Blue Cross/ Blue Shield, specifically because it offers a huge nationwide network of doctors and hospitals . . . and we travel a lot!

  • Simonne
    Posted at 30 June 2015 Reply

    Thank you for a very helpful article!
    I just wonder, how about clothes?
    We live fulltime in a smal RV and I’m really having trouble to put together a wardrobe that will suit my needs and still being small enough to fit into the really tiny closets…

  • Jan Roberts
    Posted at 30 June 2015 Reply

    Thank you Carolyn for answering another question for me. My boyfriend has sailed before (and yes, he loves Keens – I bought him a new pair for Christmas). I’ve never sailed and we’re going down the ICW in mid-October to spend the winter in Florida / Bahamas. The shoe thing has been something I’ve puzzled over (along with about 500 other things about living on a boat).

    Your website has been invaluable to me. I treat it like my cruising bible. And Dave is thrilled that I’m taking such an interest in setting up the galley, provisioning, storage ideas (his first wife really didn’t enjoy the experience). I look forward to your articles. I learn something new every time. Keep it up and congrats on selling the house so quickly.

    • Carolyn Shearlock
      Posted at 30 June 2015 Reply

      Glad that you’re finding it so useful. I remember what it was like before we cruised the first time — so many questions, and they just continued for the first year. After the first year, the learning curve wasn’t so steep . . . but I’m still constantly learning!

      • Cheryl Buckner
        Posted at 30 June 2015 Reply

        That is soooo helpful to know! Love your site and thank you for sharing your abundance of knowledge!!

  • Annie
    Posted at 30 June 2015 Reply

    Ditto Love my Keens. They are my full time underway boat shoes. Add wool socks when its cold. I have a pair of Fit Flops for my everyday shore shoes. They slip on and off quickly at the transom. One pair black sandals and one pair of natural color sandals. Covers me in about every instance. All shoes on board are non skid and non marking soles.

  • Jennifer McAdams
    Posted at 02 July 2015 Reply

    We love our Keens as well. They are very comfortable.

    We each have a pair of flip-flops to wear as shower shoes for our roughly once a week stay at a marina. Who knows how clean the shower stalls are, you could wear the Keen’s for this purpose but we don’t feel right about wearing street shoes in the shower since we would track in dirt and make a mess.
    Thanks for the list. We are new to cruising and had not figured that out about leather in your sneakers. Love your website!

  • Christine Springfield
    Posted at 07 August 2015 Reply

    Love my Keens, too! Got ’em on sale at Gander Mountain for $45.

    Thank you for all your helpful info! We pick up our 43′ trawler tomorrow and will be bringing her to Sarasota through the Lake Okeechobee waterway. Should be interesting!

  • Cheryl Buckner
    Posted at 08 August 2015 Reply

    Looking at getting some Keen sandals. I tend to have a wide but small foot. Men’s sizes don’t go down that far or I’d get the men’s shoe. And the kids shoe doesn’t offer the same support. Do they tend to stretch out a bit? Tried some on and they were a bit snug.

    • Carolyn Shearlock
      Posted at 09 August 2015 Reply

      Yes, they do stretch some. I’m always surprised when I put on a new pair how much snugger they are then the pair I just took off! Then as I wear them and they stretch out a bit, I just pull the lace a bit tighter . . .

  • Jennifer Holder
    Posted at 10 January 2016 Reply

    I purchased Keens for my husband and myself (our goal is to retire to a sailboat full time in 2016) and we wore them this past week while we chartered in the BVI. Every time my husband wore his Keens, he mentioned how much he liked them! Thanks for the info about them!!

    • Carolyn Shearlock
      Posted at 10 January 2016 Reply

      Great to hear! I always love it when someone likes something I recommended.

  • Kristi Black
    Posted at 31 January 2016 Reply

    Very helpful insight that I will tuck away for our future boat life, which will hopefully be commencing in the next 12-18 months! My husband and I both love our Keen Newport H2’s! We each had a pair that lasted us over 12 years! We are currently exploring Ecuador and on one of our walks, Kevin walked right out of the sole of one of his 12-year old Keen’s! He was tempted to have it glued back on, but I convinced him it was time for a new pair. Luckily, we found a place in Quito that sold them, so he has a new pair now! I just took my 12-year old pair to a cobbler in Cuenca, Ecuador and they glued and sewed my soles since they were also about to come off. They will definitely be our main shoes once we start boat life! They are well worth the $100 price tag!

  • Lupari Sue
    Posted at 13 June 2016 Reply

    I have 5 but 2 pairs are the same type of thongs, old ones and new ones that dont have paint on to go out to dinner in.

  • Kellie
    Posted at 13 June 2016 Reply

    I’m a Keen girl. I have had mine for a few years. I have a few pair. I live in Canada so I only wear them during the spring/summer months.
    Keen has a wide toe area, making them perfect for people with bunions, or if you carry a few extra pounds of weight. They are excellent for travelling to places that are known for dirty streets. Nothing gets past that big toe guard!
    While they are expensive and not much to look at, they are invaluable for life in and around the water.

  • Lisa Carol Kelly
    Posted at 15 June 2016 Reply

    Not gonna happen with me 5 – 7 minimum.

  • Cndy
    Posted at 29 September 2016 Reply

    The only unfortunate thing about Keen is they do not make wide shoes. I was told to go up a full size or wear men’s. I tired both. Going up a full size caused the arch to be in the wrong place and the straps too. The arch hurt and my toes hung out the straps. Wearing a men’s was not much better. I tried both for several long days of hiking and walking. I hear they are awesome shoes. I REALLY wish they made wide shoes for women. I just thought I would throw information out there in for anyone thinking about trying the options I did in order for Keen’s to fit. I am still on the lookout for closed toe sandals that will work like the Keen’s.

  • Pamela Harwood
    Posted at 31 May 2017 Reply

    Not looking forward to winnowing my shoes down to 3 pairs, not sure it’s possible, since we will be cruising in Maine, where summers can be downright chilly to the southeast and Bahamas. We will see how it goes . . . .

  • Patty Reisiger
    Posted at 15 July 2017 Reply

    Great read.

  • Brenda Greene
    Posted at 16 July 2017 Reply


  • Michele Dunn S/V Wind Spirit
    Posted at 16 July 2017 Reply

    One thing you didn’t mention about Keens is their great arch support! I really need that or I’d be miserable. Plus, you can have them customized with your choice of colors and accents. It does cost extra though. I love them!

    • Carolyn Shearlock
      Posted at 16 July 2017 Reply

      Yes, that is a big point and one of the reasons they’re good for walking long distances in towns and hiking!

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