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.
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How Not to Relaunch a Product: Belstaff Jacket
Belstaff famously makes motorcycle jackets. The brand has been reinvigorated in the past few years. This is good for awareness, but not necessarily good for integrity.
Steve McQueen famously stayed home one night rather than go out with his movie-star girlfriend in order to wax his Belstaff. This is not a euphemism. He was such a fan of the motorcycle jacket, traditionally constructed from waxed cotton, that he wore the Trialmaster series throughout his life, including at the Enduro off-road motorbike race in Europe, where he represented the US.
I knew part of this from reading of McQueen’s passion for the jacket in a magazine. I was also aware of seeing people wearing the occasional beaten up Belstaff jacket, its Union Jack proudly displayed under a front pocket. But I hadn’t really been aware of where these jackets were bought or what was so good about them.
Advertising changed that. More money pumped into marketing meant adverts in all the usual magazines, an upgrade of the London store on Conduit Street and the accompanying editorial that employing a good PR agency gets you.
So last month, with a little money to spare and searching for inspiration, I visited the Conduit Street store. It was slick – minimalist white decoration, industrial-chic storage at the back, smiling employees. But it was empty, and the staff showed an alarming ignorance of their product.
The men’s department is downstairs, which seems odd, given that I have yet to see a woman wearing a Belstaff jacket and nearly all the advertising features men. I’m aware that brands often put the women’s section on the ground floor, as they tend to be less prepared to walk flights and tend to spend more. But here it’s odd given the clientele.
More disturbing were the sales staff. Looking at two jackets, the Redford and the Belford, I asked one (female) member of staff what the difference was between the two. All I could see was one extra pocket on the Redford, for £50 more. When I asked, she picked up the jacket and had a look at it. This is never a good sign. Then she told me, that, as far as she could work out, the difference was one extra pocket and £50.

This ignorance, the distinct lack of stock, the refusal to do any refunds and the fact that so much money had obviously been spent on marketing (which is warning to anyone looking to get value for money – oh, and they obviously paid Ewan McGregor to wear one while he rode around Africa, which is not money well spent) did not stop me buying one – the Belford.
It didn’t stop me because the quality of the jacket was fantastic. From the suede lining that almost made you want to wear nothing underneath, to the durable and high quality fastenings; from the instructions on how to look after it over decades, to the odd-school paisley sleeve lining; it was impossible to resist.
The product is faultless and will find a great audience, if only they learnt a little more about pitching this to the right market with the right people. This is an old-fashioned, high quality British product. It should be sold to older, slightly style-conscious men who will appreciate it. And it should be sold by people who know what they’re selling.
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How to Dress in the Foreign Office
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.
A lovely example is found in the autobiography by Donald Hawley, a long-standing member of the British Foreign Office who was Head of Chancery in Cairo during the Nasser epoch and in Lagos when Nigeria fell apart following the coup in 1966.
While discussing the messengers that channelled information from one department to another, (one character called Archie was “not only a wholesale purveyor of unsolicited information on when Chelsea would play at home but also apt to reduce girls momentarily to tears by a bizarre proposal of marriage”) he lays out the requirements of dress in the Foreign Office:
“Dress was formal and the majority of men wore pinstripe trousers and black jackets rather than dark suits, though both were permissible. Everyone wore a stiff collar and outdoors a bowler or Homburg hat and rolled umbrella were de rigueur.” It’s easy to see how the foreigner’s stereotype of the smart, conservative Englishman was built up isn’t it? In fact, the impact of that stereotype is explained in the next sentence:
“I always wore a bowler until 1975 when an American in St James’s Park asked me as a ‘real Englishman’ [as if there were lots of impostors walking around trying to fool tourists!] to pose for a photograph. Balking at becoming a tourist attraction I gave it up.”
The same paragraph gives some correction to the style historians that claim differing parts of the same outfit would never be worn together:
“Half the staff of every department worked on Saturday mornings but everyone wore a country suit on that day of the week. Wearing this and a bowler hat we looked like Army officers and were often saluted smartly by confused sentries if we happened to walk through the Horse Guards Arch [being the entrance to the Horse Guards building close to Buckingham Palace, where the Household Cavalry amongst other are housed].”
So while you might be mistaken for an officer by parading around in your tweed suit and bowler hat, it certainly wasn’t considered bad form to accompany it with a bowler hat, even in the tradition-riddled Foreign Office. Style isn’t ever as constricted as students of it believe. The rules are never quite as simple as one thinks.
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Where Style Becomes Costume
Dressing in the full traditions of men’s clothing can make one a caricature. It must be combined with a touch of originality.
There are blogs on men’s style that are fascinating for the depth of knowledge they demonstrate – over the role of a split yoke on a man’s shirt, over the line of a shoe’s waist. They inform many things about what I buy and what I wear. But I am often a little disappointed when I see images of the authors.
This is because they seem to want to be an embodiment of what is – necessarily – historical dress, and become an illustration from an old copy of Esquire. They take every aspect of, for example, early twentieth century English country wear, and they copy it. They wear the cord trousers, the tweed jacket, the checked shirt and the wool tie. They add the flat cap, the brogues and the bright socks. They may add a hunting jacket with leather padding on the shoulder to protect from the impact of a gun’s recoil, or a waxed Barbour jacket with bellow pockets to accommodate shells.
These items are all correct, historically. And the chances are they will be of the highest quality, complement the wearer’s skin tones and fit him perfectly – as he takes great care over these elements as well. But it is just mimicry. He is in costume.
Even Prince Charles, on a hunt around Balmoral, doesn’t follow the traditions of hunt clothing this fastidiously. And he has an excuse for wearing something similar – he is actually hunting, he is actually English and all his forbears wore similar pieces throughout their history.
The style aficionado who copies it is just dressing up. He has none of the creative element that can make dressing so enjoyable, and so personal.
Let me give an officewear example. I like wearing pinstripe suits. I’m a fan of red socks, as well as double-breasted jackets and patterned handkerchiefs. But I know that if I wore all of these pieces in one combination I would look like a caricature. I might as well top it off with a bowler hat, grow a moustache and wander down Fleet Street twirling my umbrella.
So I wear red socks with more understated suits. Perhaps a plan grey flannel and open-necked white shirt. I rarely wear a handkerchief and a tie at the same time, as for me it is probably a little too much. And my double-breasted suits are not navy-blue pinstripe.
It is also fun to add touches of individuality – to experiment with odd waistcoats in formal suits, though there is no tradition of this that I am aware of; to combine smart clean Converse with wool suits, as I like the contrast of smart and casual; to wear darker coloured, wool handkerchiefs in odd jackets when worn casually. This is individuality and creativity. It is what makes dressing fun, rather than study.
I think that men who are very interested in their clothes are part geeky, petty academic and part creative, artistic aesthete. Everyone needs the former to drive them into reading and investigation, to be interested by the history and traditions of men’s attire. But everyone also needs the latter, to have the kind of mind that created these traditions in the first place. (Beau Brummel and the Duke of Windsor are heroes for being precisely the opposite of these geeky facsimiles.)
Unfortunately, when men have too much of the first influence and not enough of the second, they end up looking like an extra in a costume drama.
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The Great Bottom Button Mystery
Ooo, there’s another one! A perfectly respectable businessman with only the bottom button of his three-button jacket done up. Just the one. Leaving the rest of the jacket flapping open.
It looks so bizarre. It creates an artificial, rippling belly of negative space, and as result is surely the least flattering way to possibly do up the buttons of a suit. Why on earth do they do it?
At first, I thought it was an aberration. One man walking towards me, his pinstripe ruined by a frankly odd buttoning. I briefly wondered why he had decided to do up just that button, and not the natural waist button, the middle button. Briefly I considered it, and then dismissed it – a mistake, an accident, certainly an exception.
Then a few days later it happened again. Someone else striding purposefully along Fleet Street, briefcase in hand, importantly talking into his mobile phone. With only the bottom button done up. This time the buttoning was so low that his tie had flapped over the fastening, like a bright dead fish.
Why? Don’t you see it when you look in the mirror? Doesn’t it strike you as odd, like doing up the top button of your shirt, and no others? Doesn’t the oddity of the effect suggest that the suit was not designed to do that?
As more examples popped up, I began to give the phenomenon serious thought. Why did you never see men with just the top button fastened? There were always a few with the top and the middle, or the middle and the bottom, but the waist button was always firmly secured.
Did the bottom-fasteners somehow feel that this arrangement gave them a deeper V, a plunging, masculine chest? They could be forgiven for thinking that (though still wrong) if the suit had a natural, soft roll. But modern, worsted business suits are true three buttons – the fastening is stiff and, unlike the flannels of old, there is little natural roll. So the artificial belly is the result.
Finally, a combination of curiosity and anger got the better of me and I asked someone. Embarassing, I know. But it was beginning to dominate every waking thought.
The gentleman in question was puzzled, then a little miffed, perhaps a tad embarrassed. He said he did it because it felt like a natural fit for the jacket, it felt snug. And there’s the rub: the jacket was too big for him, so it didn’t feel like it fitted with the waist button done up. The bottom button on its own felt better.
I’ve since found that some men go for the same odd buttoning if the jacket is too small for their belly – the cut of a jacket can mean that the bottom button fits when the middle doesn’t. It all depends on cut and on physique.
Of course, they’re all wrong. It looks silly and it ignores how the jacket was designed to be worn. Any man who wears his jacket buttoned in this way should be told to have it altered.
Fortunately, I have so far resisted the urge to tell any of them this.
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