I discussed the notion with one more friend of mine (I have a total of four friends qualified to comment on this, the list is quickly approaching the end). He’s a lawyer, which I think is categorized as “more-than-sometimes-pants” profession. He promptly informed me that a man looking at all stylish will undermine him if he’s in a serious profession. He remarked:
I think for men in real business, like law or banking or engineering, anything that’s not consulting or PR, there is a suspicion of anyone who is too fashion conscious. You don’t want your neurosurgeon in a pink ascot, even if its slammin’.
For lawyers, you want to look professional and sufficiently successful, but not attract attention to the fashion per se. And trial lawyers, even the richest ones around, they stick to blue suits with striped ties. The jury cant think you’re a rich dandy, and if they’re talking about your clothes, they’re not talking about your arguments
So, we’ve come to the understanding that:
If you work at a hedge fund or meet with higher ups, you should try to look like you were born atop a pile of silver spoons, gold watches and Nantucket Red pants.
If you are a lawyer, you should look like you are a man of the people, and wear blue.
If you are Ted Gushue, you’ve got to stop wearing flip flops to the office.
None of these things will necessarily, as far as I can tell, make people think you’re less intelligent, but they will make people like you less.
But I think the most interesting response came from the third man I talked to, who works in media.