I was recently greeted by this question from Brett Berhoff who then followed the question with this simple analysis:
Do you think your clothes influence success? What will the future of clothing look like? Will every day be pajama day?
Obviously, this is a really simplistic comparison. The answer to his question using his analysis is that if you’re a billionaire then you can certainly dress however you want. What does that mean for the rest of us?
For the rest of us, how we dress matters. However, the fact that dress matters doesn’t directly imply that it means you should always dress up. In fact, some situations require that you dress down to be able to fit in with the culture of the company.
My wife told me a simple example recently of a friend who went for a job interview at a snowboard company. The instructions for the interview directly instructed those being interviewed to dress casually for the interview. Everyone who went for the interview ignored that instruction and dressed up in a shirt and tie except our friend who wore his jeans and t-shirt as instructed. We all know how this story ends, he got the job because he was the right culture fit for that organization.
The reality of dress is that the key factor in “dressing for success” is understanding the culture of the organization. How you dress says a lot about you. Are you a detail oriented person? Are you creative? Do you listen to instructions? Did you do your research to understand the culture of that organization? Are you someone who would represent the company effectively? And much more. Each of these questions can often be answered by how you dress.
The reality is that you can be an effective worker wearing a high end suit or shorts and a t-shirt. However, it’s much harder to work effectively if everyone around you is in a high end suit and you’re in shorts and t-shirt or vice versa. Understanding the culture and the message your dress sends in that culture is important. Unless you’re a billionaire, then don’t worry about it.