Men’s Style – The Thinking Man’s Guide to Dress by Russell Smith

You may be wondering what this book is doing here; what does it have to do with productivity or communication?

The answer is EVERYTHING.

How you dress affects how you feel.  And how you feel about yourself will influence how others feel about you.  Your appearance controls your first impressions and sends subtle signals to everyone around you.  So it makes sense to consider this powerful influence and to do it right.

Russel Smith writes a regular column in the Globe and Mail, based in Toronto.  This book is based off of those writings and is truly the only book you’ll ever need on the subject.  It is comprehensive, well written, and has a tongue in cheek humour throughout that had me laughing out loud.  I highly recommend it to anybody, man or woman, as a smart, funny read.

Note that the guidelines given are based off the classic style of men’s fashion and may not be for everyone.  But you’ve got to know the rules to break the rules.

“This is something Americans and Canadians often don’t understand about dress: it’s not all about you. What you wear shows what you think of the people around you. You dress, on many occasions, particularly sombre and formal ones, to show respect for others.”


  • Shoes are the single most important part of your image, the root from which your projected self grows.  Also the only item on which you must spend a great deal of money.
  • You can never go wrong with a classic round-toed oxford, either with a toecap or without, or with classic brogues.
  • A thick leather sole and leather welt will give you authority, will cost you more, and will last forever.
  • If you are just starting out with grown-up clothes, you need only two pairs of good shoes.
  1. Basic black closed-lacing oxfords
  2. One pair of dark brown or burgundy shoes.

After that:

  1. For very casual summer wear, one pair woven leather sandals or flip-flops
  2. One pair suede skateboarding shoes for evenings at techno clubs. Get brightly coloured laces in them and your friends will be impressed at your confidence.
  • Your Rockports aren’t fooling anyone: they still look like sneakers to me.
  • I would warn against very light-coloured leather shoes: grey or tan or white. They always look cheap, no matter how expensive they are.
  • Wearing any kind of sandal is courting a certain loss of dignity.
  • My favourite form of footwear with shorts is funky suede skateboarding shoes.
  • Under no circumstances can you wear socks of any colour – no, not even white – with shorts. They make you look like a dork..
  • Cowboy boots?  Forget it.
  • There is no occasion or outfit in civilized society which justifies the wearing of loafers with a leather fringe and a dangling tassel over the vamp. These shoes are an abomination.


  • A grown up man needs at least one suit for special events.   Make this one plain and flexible: a single-breasted two- or three-button in charcoal – dark grey, almost black but not quite.  You will buy this suit in a very fine wool – Super 100s or above – so that it is lightweight and you can wear it on warm spring or fall days, or even in the summer. But keep it dark.
  • After receiving your next paycheque you can buy one more suit: plain navy. Also single-breasted.
  • Next paycheque, next suit. This is one you can have a little fun with, be a little more expressive: a charcoal with a pinstripe, say, if you live in a northern climate.
  • Now you have your three winter suits, you can consider a lighter weight, slightly lighter colour for summer.
  • If the new suit fits you properly, you will not feel “dressed up.” It will not be constrictive or feel unnatural; it shouldn’t make you feel self-conscious or delicate about how you stand or sit. You shouldn’t notice it.
  • Let’s get this straight: on any single-breasted suit jacket, no matter how many buttons it bears, you never do up the bottom one.
  • So, to sum up, here are your essential suits in order of purchasing priority: 1) charcoal 2) navy 3) pinstripe 4) lighter grey (summer-weight) 5) black (fashion-forward or casual, for evenings)


  • Tweed or hopsack jackets that were “odd” – that is, not part of a suit – were not meant for wear while actually rowing or playing polo, but for wear while watching these sports. They were sideline attire, or gin-in-the-clubhouse attire.
  • The difference between a sports jacket and a blazer is chiefly in the material: where a sports jacket is textured and sometimes patterned, a blazer is of a solid, dark colour.  It is said that the name originated with the HMS Blazer, whose captain designed the prototype jacket for his sailors on the occasion of an inspection by Queen Victoria in 1837.
  • A soft wool and cashmere jacket, with charcoal trousers, a spread-collar shirt, a silk tie, and a pocket square, will make you look European:
  • The Advanced Class will wear socks that are a shade lighter than their trousers, and consider how their socks match their shirt or their tie.
  • A sports jacket and tie is less formal than a suit and tie. A suit with no tie is less formal than a sports jacket with a tie.


  • The white shirt has proved such a mainstay because it has always been a mark of privilege: you can’t keep white cotton clean if you’re performing manual labour.
  • Most men buy their shirts too small.  A good salesman will measure your neck leaving space for one finger between the tape and your skin.  Purchase a half inch larger than that for the best fit (after the first wash).
  • You want your collar to protrude just over a centimetre above the back of your jacket. You want your shirt cuffs to protrude the same amount beyond your jacket cuff.
  • In any good dress shirt you will want removable collar stays.  You can buy brass collar stays in different sizes at old-fashioned and expensive men’s clothing stores.
  • The most important part of the shirt, the part that defines its style, its character, is the collar.  The greater the spread, the flashier, and more dressy, the shirt.
  • I disdain button-down collars even with sports jackets or blazers, or at any time.  Finally, we descend to the lowest level of tacky-collar hell: the collarless shirt, the one with a narrow band around the neck and no turndown.
  • A tip for the cash-strapped A beautiful shirt and tie can save you a lot of money. People will notice them, particularly if they are bold, before they notice your suit. So if your suit is inexpensive, your shirt and tie can make up for it.
  • The new sports shirt requires a certain level of fitness, because it is fitted (that is, it has darts sewn into it). It clings to the waist and extends below it, untucked.  It has some kind of pattern on it: bold stripes, big squares, or random flowers. It has big cuffs, which you fold back only once, so they move a little as you shake martinis.  This is the shirt you wear with a black blazer and jeans, or with a fashion-forward black suit. Even with a suit, you don’t tuck it in.

Ties and Squares

  • The boldness of the solid tie is also always useful: it projects confidence.
  • Stripes, usually diagonal, have been extremely popular for the past few years, and the Advanced Class will have fun matching them with striped shirts and suits, as long as all the stripes are of noticeably different sizes and intensities.
  • The four-in-hand makes the most reliably uniform knot; it is also the narrowest.  If the four-in-hand makes a knot which is too small for the collar – that is, if the top corners of the triangular knot are not covered by the collar points – tie a half Windsor, which has an extra wraparound.
  • The easiest way to puff your square is simply to jam it in in any which way, and leave it.
  • How you match your tie and square: aim for complementary but not identical colours, and try to contrast the patterns and textures (paisley square with striped tie; smooth square with textured tie.
  • The pocket square does not replace the plain cotton hanky you should always have hidden in your trouser pocket, for sneezes and tears and for a better grip on a champagne cork when your fingers are slippery with oyster juice.


  • Victorian gentlemen hid their watches in their pockets, because a true gentleman didn’t concern himself with the passing of time.
  • The most elegant watches, the ones that connote education rather than mere riches, are the simplest and plainest.
  • Whatever you buy, stick to plain leather straps; metal straps are literally flashy and give that fatal connotation of machinery.
  • Digital watches, needless to say, are unacceptable for any outfit or situation except actual triathlon competition.

Formal Wear

  • Dinner jacket and tuxedo are the same thing; one is British, the other Yankee.
  • Every grown-up man should own a dinner jacket, just as he should own a dark suit.  But dinner jackets should not be seen before 6 p.m.
  • You will always be safe with the standard black suit, white stiff-front shirt, and bow tie. This is an extremely flattering outfit, and it is nothing to be ashamed of.

Casual Wear

  • A useful principle with casual dressing is to contrast your top half and your bottom half.
  • You wear a fine suit jacket or blazer – even something ridiculously stuffy like a charcoal pinstripe – with a fine white shirt. No tie. A silk pocket square. And jeans. You wear the shirt untucked. The final touch is the crucial one: with this you wear hip sneakers – round-toed Pumas, stripy Adidas, skateboardey Etnies. You can even have bright pink or green stripes on your shoes: the more streetwise the better.
  • Note that CEOs and senior partners rarely take note of casual Fridays.  If you consistently dress casually, you will consistently not look like a CEO.
  • Don’t treat Fridays as a day of enforced ugliness, as an excuse for giving up on your appearance. Instead, use Fridays as an opportunity to display your taste and flair in ways that the suit and tie do not permit. Note that even on Friday, you still must wear a jacket. This is the bare minimum of respectability, even if you are tieless.
  • Grown men in sweaters tend to look a little bit unravelled – sweaters do nothing for the drooping shoulders or the swelling paunch; they cling and sag.  Sure, they keep you warm, but so do cashmere sports jackets. You will always feel more confident in a jacket – which squares your shoulders and hides your gut.
  • The bikers’ uniform of blue jeans, T-shirt, and zippered leather motorcycle jacket became an instant signifier of a certain kind of masculine cool, and remains unchanged to this day.


  • Each style of underpants comes with its own mythology: one can refer to boxers or briefs or tighty-whiteys as a kind of shorthand, a code for types of man.
  • Go short and tight or long and loose. There is no middle ground.


  • If you are wealthy enough to afford more than one overcoat, you may have one short daily-wear coat in navy, camel, or dark brown, and then indulge in one longer, black formal coat with a velvet or fur collar.
  • What’s the point of walking around with the coat buttoned but the belt loose and flapping, as so many men do? Readers of this book do not flap. They never have trailing appendages. They dress in sleek, straight lines, like modern buildings and mid-sixties Mercedes.
  • A fur coat on a man speaks of vanity to the point of narcissism, it speaks of confidence to the point of arrogance: a fur coat says fuck you.
  • The belted trench coat has much gentler, safer connotations now. It means Dad. It means minivan. It means junior sales rep.
  • The trench-coat era has passed. It is time to abandon the military symbols. The confident man does not need them, just as he does not need the cowboy excess of the long, Wild West “dusters” that are sold as raincoats in stores with “Creek” and “Ridge” and “Outback” in their names.
  • The key date in the mass extinction of hats is often thought to be John F. Kennedy’s inauguration in 1961, to which he went hatless, shocking the nation.
  • The most important tip for the wearing of all these hats is the one which is most frequently ignored in North America: wear it forward on the head. Even more forward than you want, the lower the better. Do not display any of your forehead: the front brim should sit just above your eyes. If you wear it back on your head you will look like a character from Mark Twain. The farther forward, the more urban and grown-up you will look.


  • If you really can afford nothing described in this book, then scrape up your pennies and go to a barber; it is all you truly need.
  • If you are at all in doubt about your haircut, cut it shorter. You cannot go wrong with a closely cropped head: it is still the most masculine look, women still find it reassuring, no matter how fashionable the style may seem, and it should be the default option for any man averse to risk.
  • Through much of the twentieth century, any kind of facial hair was anathema to the privileged classes.
  • The key to comfortable shaving is heat. A clean cloth soaked in hot water applied to the face for a good minute before you begin, and the use of a hot shaving brush to apply soap, solve half the regularly reported problems: the heat softens the bristles and brings them up for snipping.
  • After you have finished and rinsed off the excess soap (paying careful attention to your ears, where embarrassing deposits of foam are wont to last all day), you will rinse your face with cold water to close the pores again. You will then apply some kind of moisturizer.
  • If you shave, you have to shave every day.
  • Women want their men to look grown-up, and grown-up men present themselves to the world in a way that shows that they have something important to do. They also show respect for those around them by looking clean. Believe me: the stubbly look is immature. Get over it.

“Be prepared, whenever you leave the house, to find yourself somewhere cooler than you expected to be. What if someone pulls up in a silver Mercedes, plucks you out of the parking lot, thrusts a martini into your hand, and introduces you to a countess? Will you be ready?”

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