The question
I'm the 28-year-old CEO of a multimillion-dollar company. Recently, I made some presentations to pinstriped potential investors while wearing my usual jeans and hoodie. They complained afterward that I was being 'disrespectful.' Aren't they just being old-fashioned?
The answer
Well, you have to admit, it was a calculated and provocative move. People who claim they simply don't care about clothes are not being honest. They are usually more sartorially inflexible than anyone. In your case, your frat-boy look is part of your company's brand, and it sends a message of youthfulness and sociability (perhaps your company has something to do with entertainment?).
In other words, you knew exactly what you were doing – you were trying to intimidate those old-school capitalists with your hip, tech-world ways (does your company have anything to do with computers?). They called you on it. Nobody likes to be made to feel awkward. People dress in uniforms all the time to match different social occasions, not just for themselves but also to avoid making others feel inappropriate. The bankers would have been jerks to show up at your barbecue in their suits; that would have been disrespectful, too.
Still, I highly doubt your outfit made any difference to their valuation of your company or their reports to their clients. And you knew that, too. You didn't need to play by their rules, and you were rubbing it in their face a little, weren't you?
Russell Smith is a novelist. His recent memoir, Blindsided , is available as a Kobo e-book. Have a fashion question? E-mail style@globeandmail.com .