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.

Continuing the theme of dressing as costume, the constraints of one’s job can often make one into a stereotype, especially if one works in the more traditional industries or political offices of older institutions.
I was always told that a double-breasted suit created breadth. Good for tall, narrow men. Not so good for the short and stout. This belief, though widely held by others, probably originates for me with the insistence of my mother that I would look lovely with a double breast, given that I am tall and could always be broader. 
The situation isn’t helped by fashion journalists. You can see them all crowding around the catwalks, all desperately looking for “this season’s trends”. They all have to go home and write exactly the same feature: what the runway shows mean you will be wearing (or should be wearing) next season. Because there are so many designers, with so many different ideas, a trend is hard to find. So journalists frantically cobble together examples from different shows, shoehorning one look into a trend. Sometimes journalists just give up – GQ’s coverage of the spring/summer shows went with theme of celebrating diversity.










