Reader’s Question: The Deck Shoe


Tom, Hong Kong: Simon, where do you stand on deck shoes? I’ve seen them around and think they’d be a nice compromise between scruffy converse and brogues when wearing jeans or casual trousers. I grew up detesting them for being too boaty but quite like the look of them now.

I know exactly why you have that inherent distrust of the deck shoe, Tom. I have it too.

I don’t know whether this caricature will be familiar to those in the US, but in the UK the deck shoe is synonymous with a certain floppy-haired, rugby-playing, scruffy bloke of wealth. Whether that wealth be inherited or due to “Daddy doing quite well in the city”, the uniform is the same: rugby/polo shirt, oversized sweater, worn jeans and deck shoes. Battered deck shoes. With the laces perpetually undone.

As I have little knowledge of how exactly the term ‘preppy’ is used in the US, I shy away from saying that this character is necessarily that. He certainly wears Ralph Lauren (polo shirt with collar turned up) but there is nothing forward-looking about the style – it is lazy and, essentially, a mimic of everything he sees his peers wearing (as well as his Dad).

This man has no interest in clothes, and this turns me off the idea of a scuffed, maltreated deck shoe.

That prejudice stated, I also dislike the shoe because it seems lazy in itself. The thickness of the rubber sole, the inelegance of its waist and – especially – that thick stitching around the toe. It looks as though someone has wrapped two pieces of leather around your foot and then roughly cobbled them together (no pun intended).

As a result, I tend to like a slip-on shoe more the smoother its toe. I have nothing against the humble penny loafer. It is smoother than some and has done a great many Americans a service. But it tends to be worn by men with little interest in shoes. Not all are, by any means. But most. Worn by men that just don’t like lace-ups, and probably don’t really like shoes.

Driving shoes have thicker stitching, but they can work well as house shoes, as casual shoes – to pop down the road in. I have a pair from Massimo Dutti that serve well in this regard. But the slip-on I favour is smoother – the Harrow shoe pictured is obviously a well-made shoe. The tan Gieves & Hawkes slip-on is even better. I’m not a big fan of tassles, but it is obviously a lovely shoe. Berluti ones are beautiful.

I have a blue suede pair of slip-ons of this type that I bought in Bologna. And they work best sockless, with summer trousers, as many men in Italy are apt to wear them.

As you can see, Tom, this is largely a personal opinion rather than a reasoned argument. But if you want something between Converse and a brogue I would recommend either a smooth slip-on of this type or a driving shoe – Tod’s does some lovely ones in bright colours for summer. And given the weather in Hong Kong you will probably have far more opportunities for wearing them like this than I do.


Simon Crompton is a journalist and a style enthusiast living in London, who blogs at He has too many suits.


  1. Michael, Austria says:

    Excellent written article Simon, thank you.
    While I usually agree with your views on the fashion world, I think deck shoes are treated a bit unfair here.
    I can see the point with the inherited wealth (I thought it often for myself) and you can’t wear them with a suit or at work but combine them with a casual shirt and a chino and you are ready to go for most leisure time activities and still look smart.

    Please keep your well-founded essays up.

  2. While some deck shoes are admittedly inelegant, not all deck shoes are created equal. I just bought Sebago Docksides and though they’re as casual as shoes can get, they’re still not inelegant.

  3. Michael, Austria says:

    Have the same pair 🙂

  4. Simon Crompton says:

    Interesting to hear your thoughts, everyone. I think the deck shoe is probably lost to me forever, but Bilal’s example does seem better than most.

    I suppose what it comes down to is that I find it impossible to get excited about wearing a pair of deck shoes, or to be interested in how they are made. I would find buying new running shoes more interesting.

    I’ll be interested to hear what Tom says….