Lloyd Lemons posts on the "Death of the Casual Look" in business. What people wear is a first impression and a lasting impression usually for me. I usually can remember when people wore something out of the ordinary – everyone else in suits and he in a collared shirt. Or everyone dressed quite casually and she in a suit. Some people profess to always wear a suit and I largely like to err on the side of being overly dressed than underdressed. In the early goings it was especially important for me to wear a suit all the time so I looked older in sales pitches. Now, that is less of an issue and in fact in casual business meetings or meals I like to go very casual to be most comfortable. The only pet peeve I have when it comes to business attire is when someone is clearly uncomfortable with their starched shirt, tie squeezing their neck, and suit making them sweat. This is where it hinders your ability to work.
When I first met VC Brad Feld I think he wore jeans and a t-shirt while everyone else in the meeting wore a button down dress shirt or suit (in my case). Out of the hundreds of meetings I’ve been in over the past few years this is the one and only meeting when what someone wore clearly sticks in my mind for speculation. Jeans and a t-shirt are just more comfortable, of course, but I have always wondered if there was more to it. Trying to play up a techie side? To reinforce a laid back nature? To show an independent streak? Of course, he promptly turned both the first two issues on their back by showing wide latitude in the types of business issues discussed and the intense (though friendly) conversation. In Brad’s case, I think his choice of dress worked, but I’ve also experienced people when it doesn’t. I don’t like to read into things too much, but I often link what people wear to what kind of image they are putting on display. This is especially prevalent in my high school where you have the punks (chains and piercings), the jocks (jerseys), and the nerds (glasses and out-of-control hair).