1. Backwards baseball hat, or any hat for that matter. Even in Silicon Valley, a backwards baseball hat is sure to make audience members snicker and roll their eyes. It doesn’t matter if it has the company’s name on it, it doesn’t look good. It is very difficult to listen to a CEO when you are wondering if they just woke up. And if someone can’t wake up in time for a mid-afternoon presentation, how do they run a company?
2. Sweatpants. ‘nough said.
3. The hoodie. That is so 2007. Do you really expect us to believe that you are the next Facebook? Even if you are, we don’t care.
4. Sunglasses. See hat.
5. College paraphernalia. I love my alma mater, but wearing my favorite college sweatshirt to talk with investors is a flag of insecurity. “Really, I went to this school and you should be impressed.” Or not. Save this one for grocery shopping.
6. Haute couture or expensive designer wear. If you are talking to potential investors you are asking for money. You are asking for money to pay your salary. Why should they pay you to wear better clothing than most actors unless you are starting a fashion company?
7. Gum. Warning. Don’t sit in the first row. You may get hit by projectile gum during the presentation. It happens.
8. Shorts or skinny jeans. Whoa nelly. This distraction just makes one wonder which season it is. Is this pitch for a resort? Leg hair removal? Liposuction? Plus, not many people can wear these and look professional.
9. Gimmicks. It is one thing to dress in clothes that reflect the nature of the market in which you do business. There is a fine line between looking cute and looking stupid. Even if your app is the must have for skateboarders, dressing like Hawk or White mid-tre flip is not going to show others that you can run a company. Just don’t go there.
10. Goggles – No, I am not kidding. And it wasn’t even a gimmick.
11. Dirt. Unconsciously, people connect cleanliness and competence. This means, don’t eat spaghetti before talking with others. Since I am prone to spills, I shy away from wearing white. It is sure to end poorly.
12. Like any teenager you know, even if you are a teenager. You are not, nor will you ever be, the coolest person in the room. Stop trying to be.
13. Smug smile. Why are you here?
As in any situation, it is your job to convince the audience of your story. Part of this is how you dress. If you were trusting a stranger with thousands, if not millions, of dollars, how would you want them to look? Be respectful.