5 shoes I would never wear

These days I’m doing a fair bit of travelling for work, an arduous task that provides ample opportunity for doing a spot of people-gazing. Or as is more often the case in these days where you should not catch anyone’s eye, looking at what people are wearing on their feet. Seeing how many Norwegian men wear really awful shoes, even when otherwise looking reasonably tidy, is an eye-opener. I suspect it’s not just Norwegian men either. And not only awful shoes, but scruffy and scuffed as well. Which led me to come up with a list of footwear I’d never want to be seen in.

This will be a controversial list, as I know several of the designs that cause me the most trouble are among the most loved by others. Viva le difference! One mans fancy footwear is another man’s object of revulsion. Without further ado, I’ll let rip, and leave the comment field open for retorts, support and alternative facts. Deep inside though, you know I’m right, so rather than denounce me as a fool, why not get with the programme? Oh, and I’ve left out and brand names and such, to protect the innocent (as if) and suchlike (and not be sued, more likely).

The boat shoe

Around this part of the world, there are a lot of people that arrive in boats in the Summer. The kind of guy that pops the collar of his gaudy Ralph Lauren shirt, the one with the huge logo, speaks in an overly loud voice and generally manages to raise hackles like a pro. They’re also a relic of the 80’s in the same way that bleached denim and mullet haircuts are. Yes, I know they’re a “classic”, but they’re still really nasty.

The double monk shoe

I can just imagine the scenario: The creative soul with a unique design sensibility had fallen in love with his satchel and was suddenly inspired to bring more leather straps into his life. He probably had a leather jacket made, in the style of a straitjacket, and then looked down at his feet. “Imagine, if my feet were encased in a leather satchel!” he piped. And it came to happen. The world has suffered for this whimsy ever since, though it does allow the keen shoe polishing enthusiast more canvass to polish to a high sheen.

The square-toed slip-ons

I’m offering you a double whammy of awfulness here, not only the Reliant Robin of shoe design but in a variant that is effortless to mount and dismount. There is a reason shoes are nicely rounded at the front and it’s because human foot has a pleasantly well foot-shaped form. Square them off like this and you’ve negated billions of years of evolution in one foul gesture. Add in the slip-on feature and you’ve also produced shoes for adults that just never mastered the tying of a simple knot. Darwin would have had strong words about both factors here.

The pointy-toed shoes

Similar to the square-toed shoes above, the pointy-toed variant again exists as if there has been no human evolution. Some might argue that it argues the case for intelligent design, but then a closer look makes it obvious that that’s not the case either. If an expensive sports car is the penis extension of the monied, the pointy-toed shoe must be the budget version. In either case, you’re not fooling anyone.

The duckboot shoes



Though I’ve never been a fan of the duck boot, for obvious aesthetic reasons, though I can respect that is has a utility value as a boot. A hunting boot, I believe, for trudging through the misty swamps hot on the trail of an irate turkey or somesuch. Cut the top half off though and you reach a new low of hell. What in the name of all that is sacred were they thinking of? The astonishing thing is that people wear them!


Now, I know I called this post “5 things”, and that is the concept I’m aiming for. While I was casting an idle eye around the internet looking for suitably awful pictures I could use to illustrate this piece, I came across one further variant that could not be left unincluded. Consider it a bonus, kind of in a way that compounds all that already is wrong in the world. Not a good bonus, you could say.

Apparently, this is called a mule, and fire would be too good for it

I’m lost for words.


  • Arnold N Cohen,MD 07/09/2018 at 19:58

    Much depends on your experience. In the U.S. two of your shoes, the Duckboot aka The Bean Boot, and boating shoes, are iconic foot wear for the IVY or Preppy look. Those with a true Preppy background-currently determined primarily by educational background, find those a comfortable, natural addition to their wardrobe. The other three are an abomination to God and should be gathered up and burned.

    • nick 08/09/2018 at 08:39

      As I mentioned, I can see the utility value of the Duck Boot, so by all means wear it where it has a purpose. It’s the fact of cutting off the top half and making a shoe out of the ugly bit at the bottom that defies belief. And people wear them!

    • Tony 15/09/2018 at 16:42

      Other way round. Pointed shoes, if you know how to wear them with a slim suit, are cool. Double monks are always stylish. Boats and ducks???? Never!

  • John woodward 07/09/2018 at 20:24

    Being a very practical fellow who grew up with ‘not much’ i would wear any of these shoes if I had nothing else. Otherwise i agree.

    • nick 08/09/2018 at 08:38

      I get what you’re saying, but this is an “infinite options are available” scenario. In a worst case scenario I’d probably consider wearing squirrels on my feet, style faux pas or not! 🙂

      • Skipper 08/09/2018 at 12:06

        I would pay good money to see a squirrels worn as shoes photo montage of your brothers and your good self in various, associated garb.

        Squirrel Sunday ?

  • Brownie 07/09/2018 at 20:51

    I won’t even attempt to defend the last three but on the subject of boat shoes and monks – how about the

    – Timberland Lug Sole Boat Shoe (https://shop.r10s.jp/lowtex-sb/cabinet/timberland/50009_6.jpg)

    – Paraboot William Double monk (https://cdn.shopify.com/s/files/1/0276/5047/products/paraboot_william_mokka-4896_900x.jpg?v=1502969454)

    Surely one of the two might just get the WDD nod of approval?

    • nick 08/09/2018 at 08:36

      Oddly, the Paraboot suede double monk isn’t all that terrible. I do wish they wouldn’t put their labels where they do though, really breaks up the lines, even on a Michael. I’ll pass on the Timberlands though! While I appreciate a functional sole, it doesn’t help to put the rest of that shoe on top!

  • shaun brown 07/09/2018 at 21:08

    As you well know, a lot of popular shoe styles have bee adapted from functional work or country wear. And over time have become normal day to day footwear, Brogues, Military Boots and Safety Work Boots spring to mind. This is usually after many years of minor adaptations to make comfort and style the priority rather than raw functionality ( Hobnail Boots for example). But I think some seem not to be as far along the chain of evolution, I give you Duckboots and Polo/Horse Riding Boots, but may eventually adapt into something more wearable and adaptable. To change Duck Boots straight into Shoes seems to take away their functionality, but leave the ugliness.

  • Rob Harvey 07/09/2018 at 21:10

    The square toed slip on, and lace up square toe for that matter, and pointy shoe are the absolute worst and completely unforgivable. Who in their right mind looks at those and thinks “yup, that will complete my smart look”. The others I can forgive on grounds of functionality, and well, I also like double monks.

  • Steve 08/09/2018 at 03:50

    I love it! And I agree with all of them. Give me a simple boot (or boots – Thursday Boots being my non-sponsored plug of choice), a nice brogue and a simple black lace-up.

    • nick 08/09/2018 at 08:40

      There is something to be said for keeping it simple, indeed.

  • Charlotte Engstad 08/09/2018 at 08:12

    Finally! Thank you! I could live with the pointed toe, but others are just ugly. They are so ugly that if I spot them on a man’s feet, I will turn away in distaste and never even consider to look at the rest of the guy.

    • nick 08/09/2018 at 08:34

      Finally we hear a womans perspective! Apart from having a blind spot for pointy-toes, it’s very good receive confirmation about the others!

  • Ian Haydock 08/09/2018 at 09:25

    You forgot the Crocs!

    • nick 08/09/2018 at 09:27

      I thought they’d be a little too obvious! There will be a sequel though.

  • Edward Hoare 08/09/2018 at 10:42

    Good god, I think I just found my new shoe addiction blog.
    Pointy shoes are the worst thing on that list.
    Proudly worn by everyone with not an iota of taste! There are millions of people who will go out every weekend and spend hundreds on drink and partying, spend hundreds on a financed German car…. and no more than £40 on River Island’s (~other shit holes are available~) finest sweat shop crap.

    • nick 08/09/2018 at 10:44

      That is a very astute observation! And when said awful shoes are scuffed, they are binned and replaced.

  • Dave Tabler 08/09/2018 at 17:50

    I’m guilty of loving the boat shoe. But your observation that they are associated with 80s style in the same way as faded denim and mullets feels accurate. BTW, it’s nice to see you back in the game. I’d started following your blog early this summer, and suddenly you pulled up to a screeching halt at the end of August. I missed your insights!

    • nick 08/09/2018 at 17:59

      Summer tends to be a time when readers are otherwise occupied, so a good time to take a break. I’ve got a backlog of topics now though, so I’ll endeavour to forge ahead!

  • Ian 09/09/2018 at 14:27

    There is a time and a place for boat shoes – I’ll agree with the rest of your list another comment was against crocs – but what in all that is holy “sliders” even more so with socks and shorts – on the pool side Ok (no socks), same with flipflop – but out and about NO NO NO

  • Trousers 09/09/2018 at 21:04

    The Boat Shoe is a half decent shoe, but you have to be a bit picky about choosing the right pair. I confess I like navy blue pair with a gum sole.

    Personally I don’t like Doc Martens, beloved of postmen, policemen, indie rockers and skinheads. A very heavy, ugly looking shoe/boot if you ask me.

  • Richard 13/09/2018 at 20:14

    It’s like you’ve read my mind. Not only in terms of hatreds, but ordered too! I can’t abide boat shoes or double-strap monks (or single, for that matter). I really don’t like square or pointy, but can’t say I have ever encountered mules or duck shoes often enough to have developed the same visceral reaction. I’m sure that exposure would solve that!

  • Keith Douglas 16/09/2018 at 13:27

    Hmm, I could have written that list myself, I loathe all of those styles of shoes, and the duck boot or shoe are downright ugly, although at least they have a function. I always associate boat shoes with people who want to look as though they own a yacht, but then I grew up by the Solent. Slip on shoes are for children, as are shoes secured with velcro. Boots are the only thing, specially if you live and work in the countryside. And please don’t wear black shoes with blue jeans, it irritates the heck out of me!

  • James 17/09/2018 at 18:17

    I must confess an insurmountable hatred of tram line shoes.
    Square and pointed ends are terrible but when you combine them with tramlines the bad rises exponentially. Burn them, put them in a lead lined capsule and bury them far far underground

  • Dave Scratch 18/09/2018 at 12:12

    It’s a right old motley crew. Undoubtably the pointy shoe is the worst.

    Not only do they look profoundly stupid, they have the extra risibility factor that people who wear them actually consider themselves dapper and “cool”.
    Worn with a slim cut suit they are essential fancy dress if you were going to party as one of those “salesmen” who try to stop you on the high street in a cringingly over familiar attempt to get you to change utility provider.

    No, the only person who can style pointy shoes well is Davey Stott.


  • Henry Mah 25/11/2018 at 13:51

    I’ll agree with most but absolutely love the DM’s. Dress it up or down.
    The utilitarian ones I can stomach for puttering around the house doing chores, but would never entertain the pointy shoes, what were they thinking?? New to your blog, found while researching Crown Northamptons and ordered up a pr to try. cheers
    PS I owned a pr of square toes and the super comfy Timberlands back in the day….

  • Phil James 30/07/2019 at 21:32

    Boat shoes… I have had a soft spot for them since the 80s (showing my age). I think that they should be worn with linen trousers or chinos (upper half should be a casual shirt or even a polo). I where mine in the summer mostly as there are much better shoes to be worn in colder weather. Brands – Timberland or Sebago.
    I agree with the comment made earlier that you have to be careful about the colour otherwise you look like a clown.

  • Gavin Bellerby 18/02/2020 at 00:47

    The square toed loafers are particularly horrendous.


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