The human animal is by and large easily bamboozled by the surface impressions of things. You will meet comparatively few people who see beyond the most superficial of apperances. Another way of stating this is that people want to be communicated with in a visual, quick, low-friction way. Communication is receiver based, so why not send them information on the channel that they listen to?
I. Frustration and the Technical Disposition
For the technically inclined—those who peer at nearly-identical resistors whose ratings differ by a hundred thousand ohms, or pass days in contemplation of apparently-dissimilar manifolds that are nonetheless provably topologically equivalent—this is profoundly annoying. “Why can’t these stupid people see past shallow surface appearances and perceive the real essence of the thing!?” This objection can take many other forms, including but not limited to “Why doesn’t that girl notice how cool I am?” and “Why doesn’t my boss promote me?” Most of these objections are valid on their own merits, but in practice, attempts to compete with the nature of the human animal and the nurture of superficial, visual, TV-friendly modern culture is a fool’s game. A better strategy is to accept your fellow man for who he is, and use his foibles to your own advantage. This is doubly true when ordinary people are evaluating you via their shallow heuristics.
II. Clothing is a Propaganda Expense
As a male, you’re very likely not wholly enthused about shopping for clothes and worrying about how you look. Worrying about your haircut and spending time researching personal-appearance best practices probably seem like time wasted. If you file these time and money costs in the “Fun” or “Relaxing” categories, you’re right—they’re stupid, boring, and way less interesting than trucks, guns, dogs, weight lifting, and volunteering to help the needy. But that’s a categorization error, because spending money on your personal appearance is fundamentally a propaganda cost, not something that you do for yourself.
In other words, you spend gumption on clothes, hair, and other superficials not because those expenditures make you a more complete human or a better mathematician or plumber or whatever you are, but rather because other people are stupid and you can trivially control their minds by putting on a pair of trousers that they associate with some social role. You would be grossly remiss to pass up such an easy opportunity for mind control. And when you view it this way, clothes, hair, and social skills are a great bargain for you, the buyer—in general, changing people’s minds or behavior is very difficult and expensive (for reference, examine the costs associated with TV advertising), but you’ve got the chance to do it for the price of a clean shirt, sharp shoes, and a fresh haircut.
III. Country Tweeds and City Silks
But context is quite important. As a thought experiment, consider the two pairs of gentlemen shown in Figs. 1 and 2. The former shows a pair of blandly but respectably dressed fellows; the latter a pair of genuine 1980’s London punks. If the four men had an argument in Trafalgar Square, perhaps concerned with the relative merits of the Sex Pistols’ and Roxy Music’s artistic ouvres, and this argument came to blows, whose story would the police believe, who would be handled more roughly, and who hauled unceremoniously to the paddy wagon? But if we consider that same altercation in a new venue, perhaps at a punk rock concert in Shoreditch where a rougher sort of street justice prevails, the ties and blazers would become an immediate liability.
Similarly, which of those men can a nice girl from Wimbleton use to gain social status amongst her friends? What if she’s a nice Ukrainian au pair? What if she’s a hipster chick in Brooklyn? Which fellow would be promoted first at work? To whom will the investors give money for a new startup?
Obviously these men are a contrived example, selected for maximum contrast, but the principle holds in many less extreme cases. The point is that there’s not a single correct uniform for every situation. Tune your propaganda to the audience at hand. When in doubt, dress to impress the dominant power group in the vicinity.
IV. Response as a Function of Power
Oddly enough, appearance-propaganda’s success rate will probably improve as you use it on people of higher social stature and power. This is because influential people tend to be busy, and therefore tend to rely on progressively quicker and easier heuristics as they rise through the world. As another thought experiment, consider trying to bamboozle a nine-year old into liking you with mere superficialities. Such a small child has all the time in the world to evaluate you slowly, and hasn’t yet been thoroughly socialized with his society’s coded system of appearances. You could of course make a favorable impression, but it might require quite a bit of time and effort spent on talking about toys and playing football—and even then, children often have a reliable nose for character and intentions, so the real substance of your personality would be relevant. Conversely, judges, policemen, CEO’s, and other similarly weighty folk are almost trivially biased in your favor by the briefest of efforts—perhaps something along the lines of shaving, standing up straight, and putting on a tie. This effect is partially responsible for the large number of gits in high places, who learned this technique long ago and have been using it to rise through hierarchies ever since.
V. Actionable Advice
Surely some readers are wondering how to begin, having been dressed since time immemorial by girlfriends, mothers, or Adidas. There are many right answers here, and even more wrong ones. But a known-good starting point is to saunter into Charles Tyrwhitt, T.M. Lewin, Bonobos, Banana Republic, or J. Crew, and buy navy and brown trousers, light blue shirts with button-down collars, unobtrusively patterned socks, and a set of brown leather-soled wingtip brogues. Wear the shirts untucked with sleeves rolled up. Get some V-neck (never crew-neck!) undershirts, such that the white undershirt doesn’t show beneath your open collar. Furthermore, the shirts will be too wide, so you’ll need to take them to a tailor to be darted. This costs twelve pounds per shirt, so don’t be intimidated. Wearing your new duds, wander into a barbershop in the central business district of your city and tell them you need a haircut that works in the office and also in a bar. Congratulations—you are now better dressed than 90% of men, and this uniform will get you through 90% of situations in the modern middle-class life. Of course, much has been written on this topic, and it wouldn’t hurt to peruse some of the relevant literature.
Brotip: at work, a tried-and-true algorithm is to observe the fast-tracked managers/successful employees who are one or two levels above you in the social status/corporate rank hierarchy, and then gradually dress exactly like them.