The Dude Society

An Online Magazine for Guys.

Don’t Wear This, Dude: Boat Shoe Edition

When the weather turns warm, and even when it's still cold actually, the preppy douchebags start whipping out the boat shoes. In DC, one of my former places of residence, these ugly things are practically standard issue along with your brightly color Lacoste polo (with the collar popped), and your official douchebag-club membership card.

The rules of boat shoes are quite simple:

Unless you're within 30 feet of your own boat, you should never wear a boat shoe. Are we clear?

There are degrees to the offense

Just this morning, while walking back from getting a bagel, I saw a guy wearing boat shoes. His shorts and shirt were both decent. Were I on the pier in Cape Cod, I'd probably think nothing of it... but come on dude, you're walking down West Brodaway in Tribeca. As a contrasting example, a few weeks ago we were dining at Otto (an upscale, trendy pizzeria in NYC) and there was a very high college douchebag quotient that night. Many of them were wearing boat shoes, with khakis, and blazers. As if these sad excuses for a shoe were somehow upscale, except for implying you might own a boat. I'm lucky I still had enough of an appetite to eat my dinner... I suggest you pickup a much better summer shoe.

About the author

Jamie is the Founder of The Dude Society and a New York City based web designer & developer. He really likes telling people how to think, act, and dress.

All articles by Jamie »

56 responses to “Don’t Wear This, Dude: Boat Shoe Edition”

  1. Random Girl says:

    Needed to be said.

  2. Julia says:

    alternatives, please

    • Jamie says:

      Well, if you're going for casual, the converse mentioned in the last sentence are a pretty good choice, in canvas or leather. For something a bit more formal, there are endless selections of non-nautical loafers out there. I'm not generally a fan of mandals (man-sandals), but there are some of those options too if you're in a beach area.

  3. Urban renaissance says:

    Sorry, can’t agree on this one. So can u only wear vans if you are a skateboarder? Can you only wear driving loafers if you are driving? Can you only wear desert boots if you are in the desert? Any article of clothiing can be worn wrong, but that does not disqualify it completely. I’m a fan of the site, but can’t get behind this one.

    • Jamie says:

      Well, a couple things… first, I would probably discourage people from wearing vans if they're not a skater… but that's more of a brand anyway. Sperry is the typical boat shoe, but they've branched out quite a bit as well. I own a pair of Tods driving loafers, I confess I find them extremely uncomfortable… so they've gotten little to no wear. So, again, I'd say they probably are best suited for driving. At the same time, many driving loafers would be basically indistinguishable to the vast ,majority of people who don't even know what that is. So, besides maybe having this imaginary life where you own a Lambo… you're not projecting this obviously false image.

      When it comes to boat shoes, my main objection comes down to context, attitude, and location… If I saw someone walking through NYC looking like they were headed off on Safari, which I do occasionally, I'd have a similar criticism.

      In the young-ish generation, who very rarely own boats, boat shoes are most often worn as part of an overall look that just says I'm a tool.

      Is it possible to wear boat shoes, and isolated to the outfit look fine, yes it is. I described one such scenario in the article. However, dressing appropriately for your surroundings is something I see as very important.

  4. Dave says:

    In a rare exception, a person might be able the pull them off, and I mean RARE.

    Generally, stay away! You look like a dickhead..

  5. Alexandra says:

    I'm a highly fashionable girl and guys in boat shoes always find a way to melt my heart. Sorry, this is the one time I don't agree with you guys!

    • Jamie says:

      Where do you live? My main issue is not that boat shoes can't ever be worn. I was out on Fire Island this weekend, where they are lot of actual boats, and all the guys wearing boat shoes looked totally appropriate… but when you're walking about a urban area in them… you just look like a douche :)

  6. Jess P. says:

    This is a shame as I just purchased boat shoes, for work at a country club pool of course, and have fallen in love with them. But I fought 2 years of temptation at a small private liberal arts school/mini ivy where every douchelord wore boat shoes with salmon shorts and wayfarers. But now I defend my sperrys as the most comfortable shoes I have ever owned. They are like slippers and I have a hard time taking them off. But yes, it goes along with the whole douche look. As I girl, I wonder what message I am now sending with my tan and plaid boat shoes…

    • Jamie says:

      Haha, thanks for sharing your boat shoe story. You've got a few things going in your favor 1) You're a girl and they tend to look cuter 2) You understand they're casual 3) You're wearing them at least partially ironically

  7. matt says:

    I wear boat shoes quite often. I'm not trying to convey any message. I don't care if you think I have a boat. I just like the shoes. They're cheap, comfortable, long-lasting, and can be worn without socks. That is why the majority of these "college douchebags" wear them, and it's not to make you think we're super rich yachting enthusiasts. You, sir, are projecting you're own misconceptions upon these people.

    They're shoes, dude. Why must you hate them?

  8. Ashton says:

    I enjoy boats just as much as I enjoy my three pairs of boaties. I must disagree, regardless of connotations wearing boat shoes with chinos is fine in my book even in the urban sprawl. I must agree though, with a blazer you are getting ahead of yourself.

    Regardless, you cannot beat the non slip sole of a pair of Sperry's or Timberland boat shoes.

  9. allanklimophotography says:

    I love your site, but as with some of the others commenting I can't agree with you here.

    Boat shoes provide an edgy look that will keep your feet during the warmer months. Plus these days there are a variety of designs and colors that can fit into the urban environment.

    • Jamie says:

      Haha, you're certainly free to love boat shoes, but “edgy” they are not :) In my opinion the crazy multi-colored ones are ever more ridiculous than regular ones.

    • Jamie says:

      Unfortunately, much of the anti-boat shoe comments were on twitter, so I'm a little out numbered in the comments!

  10. Scott says:

    So the alternatives here are… a pair of converse? Really? Or "non-nautical" loafers? Uh, OK. Flip flops = no. Mandals = no. Boat shoes are a good alternative and you can find them in many different styles. Yes, being the guy in the bar with boat shoes, chinos, and a navy blazer is of course douchey, but wearing some distressed canvas boat shoes with shorts and a polo on a scorching hot day is not douchey at all. Sorry.

    • Jamie says:

      You're definitely on the right track and seem to know your stuff. I'm am also anti-mandal.However, depending on the setting, I've definitely seen dudes lookin pretty douchey in boat shoe, shorts, polo combo :)

    • Jamie says:

      Is there a particular canvas shoe you like?

      • Scott says:

        these are the ones (in olive) I have (got them at Nordstrom, though):
        http://www.zappos.com/sperry-top-sider-a-o-2-eye-

        I think the thing with boat shoes is to get casual canvas ones but in a traditional boat shoe style. I'd stay away from the fancy/old fashioned brown leather ones (Ivy League douche/90 year old grandpa), and also stay away from the sneaker/boat shoe hybrids (just plain confused). Since 99% of boat shoes are in fact ugly, douchey, or both, it's hard to find the right pair.

        I, too, was a boat shoe hater for many years but came to the realization that my anti-BS stance had no real basis. I decided one day that I would look for a pair and I found some (the ones in the link). I have gotten a lot of compliments on them. I only wear them with casual clothes and would never wear them out with a blazer etc. They can work with shorts (in the right setting), rolled up chinos and oxford button-up w/ sleeves rolled etc. I think my wife actually likes these $70 boat shoes more than my $300 Hudson wingtip boots, so go figure!

        BTW, I agree with 99% of what you say on the site, just deviating on this one. I agree that setting makes a big difference in what you wear but I tend to disagree about function vs. style, though. Boat shoes may be great for sailing but my friend who sails all the time doesn't wear them. It's like watches. Diver watches are really popular, yet 95% of the guys who wear them have probably never been snorkeling, let alone SCUBA diving. Chronograph watches are popular, yet 99% of guys who wear them don't race cars, follow professional racing, or are even aware of the racing heritage of chronographs. In these days I think style always trumps function.

        Just my two cents.

  11. D V says:

    If you wear a tweed sportcoat you have to be carrying a gun in the English Countryside. That is where they come from. Blazers come from boating too. So I guess you better invent your own clothing. I shall wear Boat Shoes since I like the ocean and I live in Florida and I like to wear shorts but don't want to wear penny loafers with them, and tire of wearing canvas shoes.

  12. Jimmy says:

    PS converse are ugly and unoriginal.

    • Jamie says:

      Well, one, Converse is a brand..= . even they (to my dismay) make a few flavors or boat shoes. Two, that's just one suggestion to counteract the incredibly douchey appearance most guys assume while wearing boat shoes.=

  13. UofAguy says:

    Alright man help me out here. I'm a college senior looking to go from college kid look to young adult look. I own Chuck Taylor's but I'm looking for another style of shoe.

    I live in Arizona so I would guess the dress code here is way different that NYC, so my question is: What type of casual, everyday, shoe would you recommend? All advice/recommendations welcome and appreciated.

    • Jamie says:

      Have you tried on loafers? Going to a place like Cole Haan, or Nordstrom (don't know what you have near you) might be a good start.

  14. joe walsh says:

    well I live in gtown dc so I can attest to the original authors sentiment…everyone wears them and typically with red shorts with fish on them and a pop collar whale shirt…it's so off putting to me because everyone and I mean everyone is wearing it,m particularly among the males.. The girls do a much better job with their prep-y-ness.

    However, I have a pair of the classic brown boat shoes for practical purposes. Mainly that you slip them on and wear in the rain, you can wear them with shorts, khakis or jeans, they are cheap and versitile. I don't have to worry about getting my nice shoes messed up. If I find a similar shoe without the boat sole, I'll go with them.

    • Jamie says:

      I lived in DC for a number of years and it's definitely the epicenter of boat shoes… gtown specifically…

  15. LocDoc11 says:

    I have owned 2 lake houses, and two boats. I used to sail regularly. Since I now only own lake property (without a house on it as of yet), and I don't own any boats currently, is it okay if I own boat shoes?? I hope so because I just ordered a pair from Rancourt and Sons. Your fashion advice sucks.

    • Jamie says:

      It's funny, guys are either very for boat shoes and very against. I haven't seen much middle ground.The origin of this article was a female friend of mine saying boat shoes on men made her vag want to close up. Plus my time living in DC where every dbag is wearing boat shoes and a popped collar polo.If you like and want to wear boat shoes, go for it. It's mainly the dbag drones I'm targeting.

    • Jamie says:

      Also, if you live on/near a lake, you can wear those shoes without looking like a jackass. A topic I already touched on.

  16. muffy says:

    Your suggested alternatives were Converse… how can anything be valid -.-

  17. Nick says:

    The summer shoes you recommended (Jack Purcells) are an ugly Chuck Taylor.

  18. GBlatterspiel says:

    The only boat shoes men should buy/wear are the burgundry ones with both, woven leather top and a high white wedge sole, due I'm no designer yet, they are not yet on the market – do wait for them!

  19. Brandon Lewis says:

    Your recommendation for an alternative are Converse? You've got to be kidding. I also like how you defend wearing driving shoes, well, because you personally wear them, so it must be ok. Until you have a label of your own clothing or shoes, I suggest you stick to reviews of shows in Vegas.

    • Jamie says:

      Dude, that's one alternative. A lot of guys wear these beat to hell boat shoes as if they're fancy. There are many other alternatives too.

    • Jamie says:

      Another thing to check out is Common Projects sneakers. They are technically a sneaker, but very basic and made of very nice leather in most cases.

  20. Alison says:

    You're entitled to your ridiculous and wrong opinion. Here's mine: boat shoes are fab and yes, they do have a preppy connotation but some people like that look. 'Boat shoes' are just a name, one that you're taking a bit too literally; most of them are not functionally designed to be worn whilst boating. For that matter, you don't have to be attending or performing a ballet in order to wear ballet flats (for us girls). I live in a landlocked state and don't have any boats on the lakes either, but I love my fab new sparkly dark grey Sperries.

    • Jamie says:

      Girls have more flexibility on this issue. I've seen females wear sparkly boat shoes and actually thought they were sort of cute.In terms of them on guys, I've both met girls who love preppy looking dudes who wear boat shoes and girls who say boat shoes on guys make their vag seal up (direct quote) :)So, girls are quite divided on that, in my experience.My objection is not strictly about naming convention. It's that many dudes will put on slacks and a decent shirt, and then their boat shoes that look like they've been through a war and back. It's gross.

    • Mackenzie! says:

      Sure, they’re cute….if you’re into that whole ‘mainstream shoes’ thing…..or maybe ‘I would have never bought these 2 years ago, but now they’re popular so I’m going to buy the ugly things!’.

  21. TFM says:

    Boat shoes should be worn year round without socks. Sorry you can't afford a boat of your own.
    Also, 6 inch inseams on shorts.

  22. YJ says:

    I am really beginning to grow EXTREMELY agitated by the American perception that when a guy is “clean cut”, he’s douchey! We’re only a month and ten days from ’13 and you guys still act like cheeky high school kids whenever you see a guy who’s dressed nicely. And when in the world did Converse shoes become a fashion statement? Chucks were the shoes that poor, temporarily homeless kids wore back in 3rd grade when their parents could not afford pricier leather shoes. I personally don’t understand this type of behavior, being an American myself! Even females nowadays have developed that ‘butch’ mindset which states that they will no way in hell date a guy who’s more polished than they are. Today you walk into these ‘prestigious’ agencies in which the execs and the directors not only dress like Alabama deer hunters, they also cuss out the @$$! These are all the main reasons America is headed in the wrong direction!

  23. Dan says:

    who cares?

  24. Phil says:

    Yer a dumbass Jamie.

  25. Mackenzie! says:

    Hah, you people can argue all day about this, but opinions are opinions and nothing more. I am a Giro…and personally I hate

    boat shoes with all of my heart on guys, and girls!

    Me, I could care less about so called “designer brands” and such.

    I wear what is comfy and cute. I do own a pair of Sperry’s

    but I do not wear them because I find them incredibly

    uncomfortable! I do like Converse! Not saying they’re

    a fashion statement, but they’re comfy and come in many

    different colors. I love making custom ones online too!

    I’m not the type of person who looks for the most popular, expensive, mainstream shoe…but I do like converse! I also agree that

    boat shoes are extremely ugly, and are only excepted in society because of their popularity…and because people somehow think that

    the Sperrys are expensive. I don’t own a boat! I wont wear them!

    Sorry guys, but they’re really douchey. And on girls too. Also, whoever said they were edgy….are you kidding me?!

  26. why? says:

    why do you care so much about what other men wears??

  27. Ash says:

    Always have hated boat shoes and came across this site in an attempt to find an alternative to them in my search for some leather shoes I can wear with shorts. May have to go with some kind of moc.

    • Jamie says:

      Yeah, a casual loafer can be a good option. Wearing one that is too formal looking looks funny too, but finding one that is a bit more distressed looking can be cool. I have a pair or john varvatos ones that I wear with shorts or pants.

  28. kyle says:

    i look at boat shoes as a shoe kinda like vans or chucks. you either wear them with jeans or if you are wering shorts then you have black or whatever crew socks, Polos and Khakis dont go very well with boat shoes because boat shoes were made to be casual shoes and khakis / polos are more dress apparel. but the only douche bag in this situation is the fuck who wrote this for stating that he thinks if you wear boat shoes then you are a douche instantly…

  29. Ron silver says:

    I dont even know how i ended up in this post but like every other comment i saw, i too must disagree. I recently got into boat shoes as i have always wore closed shoes with socks for my profession. Lately i had noticed alot of feet sweat so i needed a drastic equation to my uncomfortable problem. Needless to say i bought me a pair of sperrys and bass n co. As suggested by my old man. At first the fine leather from bass n co felt harsh but as i broke them in i realized why people wore them(not only boat owners) and to think that i wear no socks would make me skeptical to even try them but now i cant take them off. I slip in them on the run and my girl even got a pair now. I can see your problem with a part of society that wears them but the shoes dont make the person so id think twice before judging if i were you. This reminds me of the people that have a need to express their hatred for others who wear different brand clothing. I recommend try them on and stop beign so judgemental, let people live how they chose to. This is a democracy and if we all started doing exactly what brainiacs like you would have us then there be no point would it?.

  30. Meh says:

    I tried to like boat shoes and got a pair of sperrys. I need something nicer than flip flops to wear with shorts. (I’m in DC, though don’t spend much time in georgetown). Boat shoes feel awful. My bare feet felt sweaty and chafed after walking only a few blocks, and I couldn’t wait to take the shoes off. I just don’t get the appeal. Plus they come with the risk of walking a fine line between casual style and d-bagery.

Leave a Reply

Your email address will not be published. Required fields are marked *