Boat Shoe Guide – How To Wear Deck Shoes, Break Them In & Mistakes To Avoid

Welcome back to the Gentleman’s Gazette! In
today’s video, we discuss Boat Shoes. I discuss different styles, how to wear them, what you
should buy, how to take care of them, and of course, history. In the early 1930’s, Paul Sperry looked at
his dog and was surprised that he had an amazing amount of grip on the ice. Upon closer inspection
of the dog’s pads on his feet, he realized that was a slight herringbone pattern. Intrigued
by this pattern, Paul started actually carving a herringbone pattern into his shoes and voila!,
he had more grip. Sperry was an ardent sailor and into boats so he needed a shoe that actually
had a good grip on wooden deck, even if it was wet. The process of getting the ridges
in your shoe soles is also known as siping. As you can see here, they’re very fine lines
in a herringbone or wave pattern which gives you that extra grip when you’re on a wet surface
that is very smooth. This concept is actually invented in 1923 by John F. Sipe and it was
named after him because of that. At first, Sperry used black soles but he quickly realized
that they would leave marks all over the boat deck which looked ugly, subsequently, he switched
to white soles because it didn’t leave any marks. In 1935, the first Sperry Topsider
boat shoe or deck shoe was introduced to the market and it was a mid-brown shoe with mid-brown
leather laces and that was the birth of the boat shoe as you know it today. Next, let’s talk about the characteristics
of the boat shoes. The traditional boat shoe came in brown, but today, you can find all
kinds of colors such as this one in Nantucket red, or in navy blue, green, you can also
find them in yellow, blue, and purple, and basically any other color under the sun. Traditionalists
stick with brown but personally, I like to mix it up and some fun colors for casual events
worn with my shorts. In terms of leather, usually, these boat shoes
or deck shoes are made with a water repellent finish such as the chromexcel from Horween
simply because the original purpose was to use it in a maritime setting. An important
feature of the traditional boat shoe is that it’s hand-sewn so you can see hand sewing
all along. In addition to that, it has the moccasin toe construction which is also sewn
by hand though today, sometimes, they’re sewn by machine. To learn more about moccasins
and driving mocs, their difference to deck shoes and boat shoes, please check out this
guide, here. Boat shoes, traditionally, feature a 360-degree
lacing system which means, that you have this white, leather shoelace go once all around.
In theory, it helps to tighten the shoe. In practice, it doesn’t really because it gets
a little loose and the leather also stretches. But, it’s simply a look and a characteristic
of a boat shoe. Most boat shoes in the market will feature two rows of aglet, sometimes
you find them with three. If you want to go for a pure experience, go with two. The original
laces were made in leather and the same color as the uppers. Today, they are often contrasting,
mostly yellow, sometimes in white, and it just adds this extra casual flair. Sometimes,
you will find something that looks like a boat shoe but it has a Vibram sole with a
strong profile and technically, it’s not a boat shoe anymore. In order for it to be a
boat shoe, it has to have white soles and it’s very classic and characteristic. Of course, fashion-forward people sometimes
go with yellow, blue, or red soles but they’re not very timeless and not very classic. In
terms of the sole profile, you will find brands like Sebago which have these thick ridges
and then others like Eastland that have these thin ridges. In theory, the thin ridges are
better for a deck and these are better for streetwear. In practice, I haven’t noticed
much difference between the thin ridges and the thick ridges. You’re probably more likely
to get a little piece of gravel in the thick ones but at the end of the day, it’s a matter
of choice. For everyday wear, boat shoes can basically replace your sneakers and they’re
particularly popular in summer, in the kind of sea or lake setting. Subject of heated
debate is whether you should wear boat shoes with or without socks. I want to settle that,
right now. Most people wear them barefoot especially when you’re in a setting on a deck
or a boat simply because you have a better grip and it suits the original style. of course,
when it’s a little cooler outside and you’re not in that setting, you can wear socks with
them. Personally, I prefer to wear them without socks. If you’re concerned that your feet
sweat too much when you’re barefoot, simply get a cotton insert or you can also go with
these socks that you don’t see and then you have the best of both worlds, you’ll get the
barefoot look but you don’t sweat as much. So, when should you wear boat shoes and when
should you avoid them? First of all, it is a summer shoe and therefore, you should not
wear it during the winter time. Boat shoes are best paired with slim jeans or pants,
khakis, chinos, or slacks. Because of the casual character, they often look good when
the jeans is kind of folded up so it looks like a turn-up or a cuff. I also like to wear
them with shorts, seersuckers, or Nantucket reds, because it can make a statement but
it’s a very casual one and a relaxed one. Boat shoes are a big step-up from sneakers,
and they also work well with denim and jeans in darker tones or also white. They look particularly
good at that setting if you combine them with a polo shirt. If you want to know more about
polo shirts, check out our guide, here. Or an Oxford cloth button-down shirt because
it just fits that whole east-coast type heritage of the shoe. Because of its casual heritage,
it’s not a good shoe to be worn with a suit, a blazer, or a sport coat. That being said,
you’ll find people wearing boat shoes with their blazer and if you can pull it off, good
for you. Overall, it’s a shoe that’s great for the
beach or the lake and any other casual setting. It’s not suited for the office or formal occasions.
It’s also a great shoe when you travel because you can easily take it on and off. When you
buy a new pair of boat shoes, sometimes the leather can be very hard and you have to break
them in. The easiest way to do that is to get into the shoe, tighten it, and then make
it really wet so the leather can conform to your foot and dry that way. If you don’t want
to do that, simply wear them a few times, but try not to wear for the first time, on
a long hike or long distance because you may end up with blisters. Keep it to short distances.
The leather can get softer over time and once they’re broken in, they’re really comfortable. So, how do you take care of your boat shoes?
Ideally, use an emulsion based shoe polish, either in that color or in neutral, like the
one here. It’s important to use those because they soak into the leather. I find these turpentine
wax paste a little too much, I only use them very rarely because they add a layer of water
proofing but if you only use them, you see cracks and it’s simply too much for the leather
and the look is not as good. I use the emulsion polish, I use the canned turpentine wax polish
once. If you take care of your shoes, they’ll develop a nice patina, however, one of the
problems of boat shoes is that they have all of these ridges and the mocs construction
so if you’re in a dusty environment, they get dirty very quickly. In that case, I suggest
you use a toothbrush and some water and some saddle soap to clean the shoes. It will last
you longer and develop a nice patina, if you keep them dirt free. Once they’re wet, either
through rain or because you washed them, make sure to dry them but in a natural setting.
Do not put them on a radiator, do not use a hot air dryer, simply let them air dry naturally.
Don’t put them in the sun either. Just like any other shoe, you should use a shoe horn
to put them on, it will help you to keep the heel in shape. of course, this is a softer
shoe, you may also want to slip in without one and that’s okay too. Your shoe will last
longer if you use a shoe horn every time. If you get stains in your boat shoes, try
to use a little bit of vinegar and water and rub on it and then it should come off and
then apply some shoe polish afterwards. Now that you know how to treat your shoes,
what to pick, what to go for, the question arises of where to buy your boat shoes? Today,
you can find dozens of boat shoe makers in the market. You’ll find anything from made
in China with the cheapest materials to made in the US with US made leather. A high-end
boat shoe will cost around $300, low end, you can start at $25. I suggest you invest at least a $150 because
it gives you a better leather quality and if you want to learn what brands we recommend
specifically, please check out our full guide here. For even more information about classic
men’s style, please sign up to our email list here. See you next time!

100 thoughts on “Boat Shoe Guide – How To Wear Deck Shoes, Break Them In & Mistakes To Avoid

  1. This video actually made me want to buy my first pair of boat shoes! Great informative video!

  2. Hello!! I am from sweden and I am goding to travel to Miami in a week. I wonder if they have boar shoes there? (Especially Sebago)

  3. I think you should make a video about cordovan dress shoes Raphael.

  4. I really don't like boat shoes. It might have to do with the obnoxious frat boys that typically wear them.

  5. Hi! In my opinion, this is the best presented video I have seen you create so far! Just wanted to let you know everything about the way you presented was spot on, the information, to be honest I can't even think of any words to better describe it to you, 10/10 for everything! I feel perhaps one of the reasons it was a lot better than your other videos (again just my opinion, so take it with a grain of salt) is you seem to be having a bit more fun when delivering it, the slightly more casual nature and your more genuine look of happiness really dial the video to 11! Cheers

  6. Wonderful video.Before watching this video,i knew nothing about Boat shoes;however,i know now a huge deal of information about them.Thanks a lot.

  7. please, for the sake of your viewers, I'm not a hater and I am not trying to sound like one but pls learn how to speak. You change the volume of your voice all the time. If you are to speak then do it in the same volume, this makes it difficult to understand you and it just annoys. So pls learn how to speak 😀 nice vid btw!

  8. Original 2-eye Sperry boat shoes go for around $100, some of the best quality on the market. I have 2 pair that have lasted me for years.

  9. My Sperry Top Sider Mako boat shoes have amazing leather and amazing water resistant protection. It looks almost brand new for wearing it almost every single day, sadly, I also ran in the shoes for almost the a year because I use my shoes for running in the morning, and the outersole is considerably worn out. Even though boat shoes are very light and even if they advertise their shoes as being tough, such as the Mako, don't run in them if you want to keep them for a long time.

  10. Sir i think u should make a video on Classic White Addidas Stan Smith Sneakers…and tell their history as they r the nicest pair of shoes in the Sneaker industry & Gentlemen Sneakers 👟

  11. There's some new startup called BoatSide USA that makes belts to match these boat shoes. They're made in the US too.

  12. nonono. no shoehorn. when you've been swimming in the ocean, you put the shoe back on with your index finger.

  13. Love wearing my sperrys but i can't stand not having socks on so I use those socks that are completely hidden (forgot what they're called)

  14. my friend wears them with long soccer socks I honestly don't think it looks good your opinions?

  15. Does anyone have the problem that the shoe release air or something… Its not a squeak but sounds like it

  16. Your photos of Nantucket Reds aren't close to the color that is Nantucket Red, just FYI. Murray's Toggery does not approve.

  17. can i wear these for fashion? for example im going to a date with someone….

  18. You know who would make a lovely Gentleman's Gazette guest presenter? Manny Delgado.

  19. Are Docksides the same as Boat Shoes?
    Also, what differs from Boat Shoes to Moccasins?

  20. Hello. In your video you mention that spending at least $150 will get you a decent pair of boat shoes with nice leather. I see that Sperry Topsiders are about $75 on average. So are these not good boat shoes to buy?

    Thanks for your thoughts on this.

  21. Good video, but there's something off about the intro music this time, can't quite pinpoint what tough.

  22. the tone of your voice is kind of annoying to hear, either it is too loud or too soft nothing in between

  23. Question please. I tried breaking in my boat shoe bye soaking it in water. After taking it out and walking around with it, i noticed some dark stains on it. Is that from water damage? My boat shoes are brown btw.

  24. IT the clown remove his make- up just to talk bout boat shoes … #respect

  25. I work for Sperry, and I very much appreciate the advice on styles to wear with the deck shoes.
    This video is very informative, and "to the point". I appreciate you for making it. 👍🏻

  26. So I got a 9.5 and they are a bit snug, the 10 are too roomy and I bit of heel slippage. Should I just stick with the 9.5 and it will fit to better as it stretches?

  27. I sometimes pair my navy topsiders with a blazer if it’s a casual summer evening event with friends, like a barbecue. I only wear trainers in the gym, so it’s great for a slightly less formal look.

  28. The best and worst boat shoes I ever got were made by timberland. One was perfect. Bought them twice before I guess they got discontinued (smh at timberland) and the other pair not constructed as good and weren’t comfy at allll.

  29. What's the comfort level on these versus a well made off-road running shoe?

  30. I prefer brown soles as they don't get as dirty and look a little less frat boy

  31. ¡He is great… any image of a boat, or the shoes being used on a boat!! hahaha!

  32. I bought a pair of boat shoes from Rancourt and they’re far better quality than the standard line Sebagos or Sperrys (although pricier too). I’ve heard great things about Quoddy too.

  33. I wear knee high nylons with them to work with my scrubs as a dental hygienist:)))) love them:)

  34. Boat shoes also make the best slippers. Last a lot longer that real slippers.

  35. Boat shoes give me blisters in the sides of my ankles and sometimes in the back of it.
    Any tips for this to stop?

  36. Hey can someone tell me if boat shoes go well as a busniess casual shoe or go for something else

  37. I just wanted to know if boat shoes let me run at pe because I have to wear them instead of my rebooks

  38. My shoes has a kiwi stain.I put tooth paste and it change color of my shoes.I put alcohol and it the color more please help me make the shoes at original color


  40. I wear these because they show my $30 socks. I like looking at my socks

  41. I bought Timberland ones, very happy with them. They were around £80.

  42. Reminder if you have a boat shoes (top sider) dont pair it with a long sock or sports socks cause you look like a soccer player with a long socks and with a pair of boat shoes hahaha! just buy a foot socks thats the pair of boat shoes makes you more looking stylish men even with or without earings or any jewelry it will make you look so good.

  43. Who came here right after Alpha M told them never to wear boat shoes? 😉

  44. Dark tones laces in same color
    Don’t use shocks
    Only with shorts

  45. I know this isn’t intended to be a catch-all for deck shoe info, but I do wish more had been discussed about the differences between shoes worn on-deck and shoes simply styled in the boat shoe manner. For instance, the Sperrys I wear to church are very appropriate for casual wear, even with a tie. The shoes I wear on the water are VERY different. They’re vented, to allow water to enter and escape easily, and wouldn’t look right in many other applications.

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