It’s upon us again, dear diary, that most dreadful day for office workers around the world. True, the weekend is nearly within our grasp, and perhaps you think William T Fitzgerald is looking at his calendar upside down. But I refer to that awful tradition of self-immolation, that scourge of the white-collar male, that self-inflected wound that started out as a benefit but has morphed into a folly: Casual Friday.

Any other day of the week, we alpha dogs face a few simple but clear decisions. Blue or black, solids or pinstripes, loafers or lace-ups?

Although our choices are few, they do matter. Take the colour of the suit.

Plain black is frankly boring, too heavy a strip makes you look like a convict, any off-the-wall silvers or browns can make you stand out for the wrong reasons. I usually opt for navy blue or dark grey.

Then it’s the shirt. Again plain white is the boring option; the danger of being mistaken for a waiter is significant and potentially career-breaking*. Coloured shirts can work well, but what about those ones with differently-coloured collars and cuffs. You know, the blue length and the white trim. Buddy, you’re not a yacht.

Nevertheless, if you throw in a bit of colour or a little gingham, it’s a nightmare to find the matching tie. I opt for a pastel pink or blue shirt. Strictly double cuffs, and Hong Kong humidity be damned.

This allows my one concession to display my sense of humour; witty cufflinks are so much better than comedy ties. My favourite pair has ‘Buy’ on one side and ‘Sell’ on another. Maybe on a Friday I’ll wear the ‘Hot’ and ‘Cold’ tap ones – always raises a chuckle in the office.

Our CEO, Kim, has a penchant for cartoon ties, the ultimate business faux pas. Even when we have client meetings, he’ll turn up with Fred Flintstone or the Three Stooges hanging from his neck. Perhaps he thinks this endears him to others.

And when Kim decides to sport a bow tie? Don’t get me started.

Now, in this part of the world, most of us have our suits and shirts tailored. Maybe it’s not Oxford Street, but Hong Kong’s finest can deliver something light years beyond what you’re gonna get at Marks & Sparks or Macy’s for the same price. And if you still want to go off the rack, there’s plenty of the top brands at Lane Crawford.

Guys, it’s not that difficult.

Yet my colleagues roam around in ill-fitting outfits, horribly clashing colours or, worse, three sets of stripes all at once. And even those who somehow manage to get the ensemble right tend to screw up on the shoes. Mate, Zegna or no Zegna, those dusty rubbery things make you look like a Kowloon boiler-room hack.

However, my ultimate no-no is the monogrammed shirt. I admit, this may be an obsession particular to me. When I first moved here and acquired my inaugural Hong Kong tailored suit, the tailor showed a bit of initiative and stitched my initials into the cuffs. But nobody wants to entertain clients with the initials ‘WTF’ on their sleeves.

Diary, I have digressed. My concern is not what goes on Monday through Thursday. My concern is what we’re wearing today. Casual Friday.

For up-and-coming execs such as yours truly, Casual Friday is a minefield.

You can’t dress too young, lest they fail to take you seriously. You can’t dress too old, like a fuddy-duddy. You must be kitted out soberly enough to reassure the boss, but with enough pizzazz to catch the eye of the office girls.

What’s that I hear? It’s worse for women? Right, like the one who just strode past my desk wearing tight jeans and a low-cut top, which seems to be the consensus outfit amongst the sisters today.

Believe me, girls, I know what’s going on. The trading floor’s more like a catwalk-turned-boxing ring.

Now, at most American firms, the default setting for guys on Casual Friday is a blue shirt (option: polo), chinos and loafers. Reminds me of those times maybe five years ago when there were anti-capitalist demonstrations in New York. Firms told their employees to dress down for the week but everyone ended up wearing exactly the same outfit, making them an even bigger target.

Of course, the idea of Casual Friday is to make people more relaxed and empowered. Does it work? Not a bit. People in my office simply turn up later than usual, take longer lunches, chat more and finish up sooner. Give a guy some slack…or rather, slacks…and he takes the Mickey.

*Speak for yourself, garçon. –Ed., in a crisp white shirt.

William T Fitzgerald is a fictional character, as are all the other individuals and companies in “RFP Diary”. Any resemblance to the living or to real firms is purely coincidental. Will’s adventures continue fortnightly.