The Great Suit Debate
Software entrepreneur Mark Cuban explains "Why I Don't Wear a Suit and Can't Figure Out Why Anyone Does!" He started out with a bad attitude:
I bought both of those polyester wonders, one Grey pinstripe, the other blue pinstripe for a total of $99 dollars plus tax. To go with those fashion forward wonders, I had several white polo button downs that I had purchased used from a re-sale shop, and a couple ties that I had bought on sale or had gotten as hand me downs from friends.
Cuban's bank account got a lot better, but his view toward suits only got a whole lot worse.
After I sold MicroSolutions I decided that I never would wear a suit again. I was able to hold true to that while I was making a lot of money trading stocks for the next 5 years, but then Todd and I started AudioNet which would morph into Broadcast.com.
With our new business, I decided that I would have to wear a suit, but would modify the rule so that I would only wear a suit when someone I was selling to was wearing a suit. If they were selling to me, I didn't care if they were wearing a tux. I was going to go comfortable and not wear a suit.
When Broadcast.com was sold, the suit went out the window completely. I vowed to never wear one again other than weddings and funerals, and only then because it wasn't worth the hassle to deal with people asking why you didn't wear a suit. I'm certain the people getting married dint care, and I don't think anyone is going to be looking down at me wondering why I showed up at their funeral without a suit. Suits make no sense whatsoever.
One problem with suits that Mark Cuban never really discusses, probably because he now has so much money the difficulty never occurs, is the utility of wearing a suit as a function of your available budget. Because if there's one thing everyone agrees is worse than a suit, it's a cheap suit. Here's an Australian realtor warning customers against doing business with people attired by the sort of tailor I can afford. Now if an Australian real estate agent can look down his nose at you then it is proof you are in real trouble. "Home sellers should be careful and expect to receive what they pay for, because let's face it, if you pay peanuts you can expect to receive the service from a suitably qualified monkey dressed in a cheap suit." Ouch.
The other thing that Mark Cuban missed is that some people naturally look good in a suit, while for others, it never works, no matter how much it costs. To see what I mean, imagine Daniel Craig and Danny de Vito. But it's more than just a matter of bone structure. I've noticed that most people who look good in suits are actually comfortable wearing them. Like they grew up in a family where you put them on like t-shirts. So should you hate them? I guess it depends on what kind of person you think you are.