How to Dress for Success in Five Simple Rules

An attractive woman with a pleasant, open face stepped into the elevator beside me. Ever since I became a Property Consultant in Hong Kong I have made a point of reaching out to strangers and engaging them in conversation. I want to expand my social network. Everybody needs a place to live, after all.

“Do you think it’s stupid to wear a tie in this hot weather?” I asked, displaying my costly strip of patterned silk for her consideration.

“No!” she replied without hesitation. She seemed pleased with the opportunity to express an opinion on the appropriate business attire for men. “I think you look good!”

“So few people seem to take the trouble to dress properly these days,” I confided, “but I like to wear a tie even in this heat.”

“It is really hot!” she agreed.

“I’m sweating like a whore in church,” I confessed and spread my arms so that she could better observe how closely my damp shirt was sticking to me, “but I’d be sweating just as much even if I was naked.”

She discreetly stabbed at the elevator buttons.

“It’s not so much the heat,” I explained, “it’s the humidity.”

The elevator doors parted with a swish and another potential client bounded nimbly from my burgeoning social network.

Twenty five years ago my good friend Eli lent me a book called “Dress for Success” by John T. Molloy. Eli was a charming, likeable man, older than me, who was always immaculately groomed. He wore an obvious toupee and a pencil moustache. His grey suits were tight and his white shirts appeared to be fashioned from nylon and possibly ironed directly on to his plump torso. His thick, black body hair showed through the translucent fabric and one couldn’t help thinking that he must be an outstanding candidate for a transplant. I therefore regarded his book with a degree of suspicion.

“You’re clearly a bright young man,” said Eli, “but your fashionable look is holding you back from true success in your career!”

Eli was Managing Director of his own grandiosely named company, Royal Lineage Film Productions. His business model was to send out girls with cameras to popular tourist spots where they would surreptitiously take Polaroid pictures of smooching foreign couples, insert the instant photographs into transparent plastic key rings and then courteously offer to keep these holiday souvenirs unless their victims coughed up a modest sum to protect their privacy. I wasn’t sure that I was ready to handle Eli’s heady level of true success but nevertheless I accepted the book in the genuine spirit of generosity in which it was offered.

I read it cover-to-cover and recognized the truth of the advice. I changed the way that I dressed. All at once bank clerks welcomed me with a smile. Taxi drivers sat up straighter and drove me directly to my destinations. Ladies opened doors for me and insisted I go first. Customers signed disadvantageous deals based on nothing more than a first impression.

And yet, as Eli amply demonstrated, it was possible to carefully study this remarkable book and still fail to achieve the desired results. Perhaps Mr. Molloy’s research was too voluminous to be clearly understood. Perhaps he had left too much room for personal interpretation. Without further ado then, I have refined and condensed my own principles of dressing for success in the ubiquitous manner of our times into Five Simple Rules. Here they are:

1) Dress for success, not to impress! This is a crucial concept which I cannot emphasize enough. Your aim is not to make a positive impression; it is to avoid making a negative impression. A fashionable look that makes a statement may impress a few trendy peers but the majority of people you meet will not take you seriously. That’s what we mean when we talk of fashion victims. Wear no jewelry other than a wedding ring and a tasteful watch. Your trouser belt and shoes should be black leather. Captains of industry do not wear brown shoes except when shooting grouse or gardening. My research shows that Mark Twain, Abraham Lincoln or Oscar Wilde said, “It is better to remain silent and be thought a fool than to speak out and remove all doubt.” If your attire is speaking out loudly I absolutely guarantee it is saying something foolish.

2) Be clean. Wear your hair short, clean and dry — no gel, no shine, no grease. If you wear a ponytail you must immediately rush to have it cut off before wasting any more time attempting rules 3, 4 and 5. You should be clean shaven. Stubble and beards are for film stars and Vikings. Finger nails should be clipped short. If you are approaching my age, you will have coarse hair erupting from your nose and ears and your eyebrows will be attempting to escape. Trim them with scissors or a small power tool if necessary.

3) The Rule of Three. A man has three elements to his business dress: his suit, his shirt and his tie. They should contrast and complement but never match. Of these three garments any one, but only one, may carry a pattern. If you wear patterns on two elements simultaneously you are probably Tim Gunn or an architect. If all three are patterned you may be suited for a career in the circus.

4) Fit. Many years ago I was a “fit model” working for several famous fashion designers. My qualifications were that I had perfectly average measurements and nothing more lucrative to do during daylight hours. This educational experience taught me the secret of the well-dressed man. His clothes fit. So get your suits and shirts made by a good tailor. They may even cost less than if they were off the rack.

5) Fit in. Dress appropriately for your industry. I need to reassure sceptical clients that I am competent to advise and act for them in a property deal. I dress to project credibility and authority. My dear father, by contrast, dressed in sports jackets with patches on the elbows and he mismatched his shirts and ties. He had grown up on a sheep farm and had only to discard his flat cap to fit in at the Physics Department where he herded photons and taught nuclear secrets to attentive foreigners.

Men in open-necked shirts obviously travel by bus or tram. They struggle to the office in the morning among the sweaty, teeming masses on the MTR. Men in jackets and ties, on the other hand, clearly must be making deals in the cool comfort of the Hong Kong Club and traveling around town in an air-conditioned limousine.

Have you noticed the way that presidents and newsreaders dress? If you wish to speak with authority you should emulate them. If your clients question your advice or your employees question your decisions, it may just be because you are dressing for failure.

Dressing right won’t guarantee success in your career. If all you know is how to dress you will soon be found out. But dressing poorly is self-sabotage. It’s hard enough to get ahead, don’t you think?

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