I called, then, on Ted Gushue, who is not only very brave about putting his name on his stories, but also is some kind of style icon. He told me a very sad story which runs thus:
In the middle of the dog days of summer I’d accidentally pulled a major workplace fashion faux pas: I wore flip flops to work. Now normally I wouldn’t think too much of it, I sit at a desk and most wouldn’t notice – but on this day I had a meeting with the higher-ups at work, and as I do in most meetings when sitting down to settle in, I cross one leg over the other.
Upon crossing, the entire meeting was brought to a halt as the president of my company said something along the lines of: “let’s all take a moment here to stop and admire Ted’s naked feet.” Completely brutal. I was mortified, and for a split second was genuinely concerned for my future at that job.
As for cheap suits/poorly fitting suits I’d certainly say that it would hinder your progress through the corporate ladder. If you are oblivious to the fact that you dress like a schlub, the chances are you aren’t doing too terribly hot in the other areas that matter either. The biggest drawback to wearing an ill fitting suit is more about what happens after the 5 o’clock whistle blows, translation: the boss might not tap you on the shoulder for that all important drink that could shape your career.
The main thing I took away from this is that one should not cross one’s legs like Cary Grant at meetings – although that sounds like a very dapper move – but the message still seemed to hold that if you dress in a way your boss does not dress, they might like you a good deal less. Which amounts, I suppose, to the same thing as being thought less intelligent insofar as it will limit your career advancement.