Silhouette and Fit: Know the Difference
A suit with massive shoulders, tiny waist or short trousers does not necessarily fit badly. It just has a bad silhouette. It is important to understand the difference.
The shoulders of your suit, for example, may end exactly at the edge of your actual shoulders, continuing in one smooth line down the rest of the sleeve. They may, alternatively, extend an extra half an inch to an inch. The line of the shoulders may be square and straight; they may be concave, curving down from the collar and then rising toward the outer edge; they may even be slightly convex.
Any of these styles may fit perfectly. If the shoulders are to extend slightly beyond your actual shoulders, and have a square, boxy line, they will require extra padding and support. If they are to curve naturally and with a slightly concave line, they will need to be carefully aligned with the line of your own shoulders, lest these ruin that line.
The point is, these variations create a different silhouette. They do not necessarily fit better or worse than the alternatives. Silhouette is more akin to colour or pattern – it is a personal choice, but one that can still be made badly (or, to be more generous, unsuitably).
The relationship between these two continues around the rest of the suit. The waist, for example, may be designed to be more or less pinched, creating a more or less defined skirt. If the suit is designed to have a generous waist, but you buy a smaller size to try and achieve a pinched waist, the wool will ripple with complaint when you button up the jacket. You have confused fit and silhouette – in trying to achieve the latter, you have failed in the former.
It is also likely to fit worse elsewhere, as you are deliberately buying a size too small. Your shoulders will press against the sleevehead. The back will feel constricting.
If the suit were designed to have a pinched waist, the wool would be darted, with slivers of material taken out and sewn back up again. The shoulders and back would fit fine and you would have achieved your desired look.
Silhouette is about what a suit is designed to look like. Fit is about whether a particular size of that design fits to your body. Don’t confuse the two. Be aware of what the suit and its designer are trying to do. Then judge its fit.
- As an addendum, a few quotes from Nicholas Antongiavanni about silhouettes: “Designer suits may be gargantuan or minimalist. With these it is not so much their level of comfort that fails you but their lack of harmony. A jacket that fits perfectly but is ridiculous in silhouette is useless, even more so than a jacket tasteful and sophisticated in silhouette that does not fit; for in the latter case in may be altered whereas the former is always harmful.
“When he said to me that the Americans do not understand fit, I replied to him that the French do not understand the silhouette, because if they understood they would not wear such square-shouldered, box-hipped, skin-tight jackets. The greatness of the English and the Italians as dressers is caused by their silhouettes, and France’s ruin caused by theirs. And because of Americans’ obsession with fashion, many of these have spread to our shores.”
The Allure of Tweed

I was flicking through an extremely large volume on vintage fashions when I visited my parents at the old homestead for Easter, and though my flicking was casual and intended for pleasure alone, I began to appraise the pages as though a student; I started to notice patterns and similarities. Between the Edwardian ladies with their bicycles and straw hats and the late Victorian country gentlemen with their shotguns and deerstalkers, there were few similarities. In nearly all respects, they represented the very ’Mars & Venus’ stereotype that defines and separates the sexes; the gruff, brawny hunters and the delicate ladies of fashion. However, fabric seemed to be an area they could agree on. One fabric at least. For there was, in those days, a great preponderance of tweed in clothing.
Tweed now has neither the status nor the broad appeal it once boasted. Like other British institutions; the Lyons Popular Tea Room, the music hall or the pier, it has faded into that sepia world of yesterday. It seems to have been pushed into premature retirement to appear alongside shortbread biscuits, raspberry jam and Earl Grey tea in English Heritage gift shops.
A great shame this is, for tweed is one of the most practical and sensible fabrics ever made. Moisture resistant and extremely warm, for those wishing to spend time outdoors without Gore-tex, tweed is a wonderful material. And, though very much a country fabric, in these days of leisure clothing, tweed is seen as an equally smart alternative to finished wool fabrics in a metropolitan context. A good friend of mine frequently adds his Harris tweed jacket to his casual shirt and trouser ensembles to great effect.
If tweed has any status, it is that of a material favoured by the aristocracy. This is hardly surprising, considering the aristocracy are frequently those in possession of large estates, on which outdoor activities take place. A snobbery has been attached to the wearing of tweed in recent years; an inverted strain. Anyone wearing tweed is likely to be seen as a ’tweedy’ person; an assertion which does the fabric a disservice. Characters of all kinds have worn, and will continue to wear, tweed. Taking the decision to ignore the extraordinary negative stereotyping and add this most majestic material to the wardrobe requires an open mind and a little consideration of purpose.
The tweed suit
If you are planning to go the whole hog and look into the purchase of a complete tweed suit, you are to be saluted. I rarely see tweed, worn in such volume, on one person. It is magnificent, but would require a good deal of research. Harris Tweed is perhaps the most famous tweed available, although there are those that consider the loss of the old methods of hand spinning and natural dying to be detrimental to the quality of the fabric and the brand. If you prefer your whisky with an ‘e’, you might consider that Donegal tweed, Ireland’s answer to Harris, is the fabric of choice. Donegal tweed is hand woven and naturally dyed from the flora surrounding the sheep on the hills of Donegal, Ulster; moss, berries and fuchsia providing some of the colours. I always think it would be sensible to go for a three-piece suit.
The tweed jacket
Tweed jackets are an excellent odd jacket to be worn casually. They are perfect for a weekend away from the city, although having said that, they never look out of place as daywear in the metropolis. Choosing a tweed style depends largely on personality. I myself, being of a somewhat unrestrained and egotistical nature, might choose a rather brightly checked tweed, although friends of mine with a taste for something a little more subtle, might choose a quiet tone-on-tone check or a simple brown herringbone. If you are selecting a check, I think it advisable to keep to Breanish or Harris as the light weight Border tweeds are particularly fuddy-duddy; redolent of school teachers and retirees.
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.
Fitting In On Wall Street
So you want to be the next Gordon Gekko? Think you’re a master of the universe, ready to wheel and deal with the big guns on Wall Street? I spend a fair amount of time with those guys and though it’s been a rough couple of months in the Big Apple, most are still looking pretty sharp.
Even with the financial market’s current turmoil, Wall Street continues to grind away at the business of business. Every day, newly minted MBAs surge into New York, hoping to take their places at the feeding troughs of profit. Though movies usually focus on the sexy, glamorous side of the industry (how unusual), the reality of a typical Wall Street starter job is one of emotionally exhausting financial analysis, intense competition and 20 hour days.
If you still want to take a shot at the brass ring the upside is that working on Wall Street can be a very rewarding career - literally. And to make a good impression with both your clients and colleagues, you’ll need to know how to dress.
Sure, the idea of the maverick trader or brilliant iconoclast is what plays well on TV, but in truth Wall Street is a very conformist environment. If there is a prominent color palette, it’s grey. And if there is a defining trait that sets the leaders of the pack apart from everyone else, it’s the quality of their stuff, not necessarily the flash.
The pinstripe suit is the uniform of New York’s financial community. Its inherent sobriety and maturity lets your clients know that they can trust you with their money. No matter how much you’re pulling down, the job of your clothes is to project conservative seriousness.
For those who are moving up the ranks and ready to show off, the name of the game is quality. Where other environments might celebrate flash and obvious excess, Wall Street eschews it (at least out in the in open). In this extremely competitive environment, projecting success and advancement without breaching the “code of grey” is the name of the game. Here are my observations from the Street.
The suit is where it all starts and when it comes to suits, bespoke is the pot of gold at the end of the sartorial rainbow. After depositing your $10 million bonus check (as several Goldman Sachs guys did last year) nothing says, “I’ve arrived” like a couple of suits made to fit you and only you. That kind of success also allows for wider wardrobe options like gen plaids, country windowpanes and the in-your-face attitude of a nice fat chalk stripe.
Custom made suits, where you are matched to an existing pattern tweaked to fit your frame, is the next best thing and certainly nothing at which to sneeze. Many well known fashion houses and tailors offer this slightly more affordable option to the up and coming traders and bankers of the world.
If going with off-the-rack, labels like Brioni, Kiton, Zenga, Kilgour, Canali, and Ralph Lauren are always good choices. Double vents are de rigueur in most cases, though single vents are perfectly acceptable for American makers like Brooks Brothers, J. Press and Oxford.
Almost to a man, French cuffed shirts seem to rule Wall Street. Younger guys in particular like the versatility they offer, along with the associated spread collars and cufflinks. Thomas Pink and Charles Tyrwhitt have made significant inroads in New York. Still highly respected is Turnbull & Asser, famously worn by Washington Post editor in chief, Ben Bradley. And when it comes to cufflinks, I’ve seen everything from subway tokens to solid gold bulls and bears. They are one of the few truly personal accessories a man can wear to the office, so great care is usually given when picking them out.
Ties are another area for individual expression, though again in a somewhat restrained fashion. Hermes and Vineyard Vines are popular in part because their classic and sometimes quirky repetitive designs possess a timeless quality. Of course these premium brands are very distinctive and instantly recognizable – another way to telegraph your taste. For those seeking a more traditional look, Brooks Brothers repp ties are a safe bet.
Footwear is often confined to the cap toe oxford or slip-in loafer; I don’t often see wingtips. Even though brown shoes pair wonderfully with grey, more often I see black. As with tailored clothing, when you can afford it, custom shoes are favored. Names like Edward Green and John Lobb are voiced with idolized reverence.
Of all the accessories that Wall Streeters use to indicate their status in the financial food chain, the wristwatch is king. And the king of wristwatches is still Rolex. I’ve lost count of the Submariners, Sea-Dwellers and Datejusts I’ve seen. Interestingly, when it comes to chronographs, the Omega Speedmaster in particular and Breitling in general seem to be the most popular. I suspect that even for high-flying money managers, spending $25,000 on a Rolex Daytona is a little excessive.
Overall, the Wall Street look is a classic one, steeped in purpose as well as iconic style. Elegance, attention to detail and luxury touches are its hallmarks. Of course, not everyone in the industry dresses this way; some are utterly clueless and others are dandies in the extreme. Nonetheless, this distinctive and polished style of dress has come to define what it means to be “Wall Street.”
Elegant Loafing

Laces: who needs them? When I was a young lad at school, purchasing shoes was a regular activity. My feet grew rather quickly in my early teens and I was taken to Russell & Bromley sometimes three or four times a year. From the comparatively small selection available in their woefully decorated stores (Eighties kitsch), I nearly always pointed to slip-on shoes. As a wide eyed and naive child, I had no tolerance for acknowledging timeless style or the hoarder’s instinct to collect ‘essential’ shoes. Slip-on loafers appealed to me because they were ‘cool’; they were untucked shirts and ink-stained trousers, the knowing grin of the worst behaved boy in the year and the loud, battered jalopies screeching from the school gates at a quarter to four. Buying them represented access to the world of the scruffy and popular; not buying them meant relegation to the ranks of the laced-up lab crew – the sort of people who now possess houses, careers and a Mercedes Benz. Oh, the utter stupidity of youth.
Now, loafers mean far less to me. I am certainly taken by a dashing design and interesting colours but I now prefer the structure and the drama of a lace-up. Having said that, loafers have always been important shoes when spring gives way to summer; especially my Tod’s driving shoes. Try as I might to find discomfort with my penny loafers, they have been faithful and extraordinarily practical; a duo of burgundy and black shoes from Bass Weejun they have retained their classic shape well throughout years of service. Indeed, to me it is clear that it is the loafer that is the Bordeaux of shoes. When spanking new, they look a little stiff, if a little dull. Once they get accustomed to the foot inside, they relax; they age beautifully and gracefully and even in old age, when they have ceased to be suitable for metropolitan rendezvous’, they make fabulous garden shoes.
There is still a healthy public demand for loafers. Pennys are rare, and for many less nostalgic than myself, a little dated. Longer shapes, unconventional colours and retro styling are becoming the commonalities in modern slip on shoes. Fashion houses such as Gucci have continued their love affair with laceless shoes; indeed Italian feet-chic in general is epitomised by the naked ankle and classic loafer. Shoe giants like Tod’s and Moreschi, famous for their production of casual and yet noticeably smart slip-ons are popular as ever, despite the fact that their customer base, at least on the streets, seems to be aging. A knowledgeable pal informs me it’s a peculiarity of culture. The English are not nearly so smart when it comes to dressing down – a statement pungent of paradox but vitally true. Chaps see the opportunity of discarding their office lace-ups, generally speaking, as a chance to put their feet into a pair of snug trainers whereas Italians and other continentals prefer driving shoes and supple leathered loafers. And they are remarkably comfortable, even more so than trainers.
With our less than clement summers it is perhaps understandable that we do not turn to Mediterranean chic on the change of the seasons, but when the weather does favour those in colder climes it is a great opportunity to give a pair of elegant slip-ons a runabout; a swinging slim trouser, some exposed ankle and of course, some of that schoolboy nonchalance.
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