This is the first of a series on Stylish Entrepreneurs (sponsored by Gillette, yeah!). I’m going to take a closer look at the personal branding of some famous technology entrepreneurs. Who exactly? Well, Kevin Rose, Ryan Carson and some other names you should be familiar with.

I’m starting with one of the most respected and recognizable entrepreneurs in the world: Steve Jobs.

Steve is interesting for this series for several reasons; he is a geek, an icon and he clearly has style.

Is Steve hip? Fashionable? Hmm, not really. But you can give almost anybody in the world the following description and they will know who you are talking about: New Balance Sneakers 993, Levi’s 501, Cashmere & Silk black mock turtleneck.

Steve Jobs doesn’t seem to alternate his wardrobe much. But if we look really close there have been some subtle changes over the years. Would you believe me if I said he once wore a white mock turtleneck? He did, at WWDC 99. He has also been seen in suits (including bow tie!) and with a suave leather jacket at the Apple Store New York opening. Some of Steve’s alternative wardrobes:

Yeah, all Steve. But we will always remember him as the guy with the jeans and black turtleneck. Like this:

So why does he do it? Is it boredom? Doesn’t he care? Some people think having a repetitive wardrobe is said to be symptomatic of Asperger Syndrome. Could be it. My guess it isn’t random or compulsive but calculated, as everything else. Steve carefully crafted himself a public image, and the turtleneck and jeans paint a picture; he is casual, smart, stylish and agile, all in one.

You would make a fool of yourself wearing the same thing (although I did start wearing New Balance shoes a while back, and Steve certainly influenced that) but if you want you could. The website will help you become a Steve Jobs Lookalike with a few clicks. They do have the turtleneck wrong though. Our sources say the turtleneck is made by St. Croix and will cost you close to $200.

So how do you dress? Do you think its important to have ‘a look’? Do you even think about these things as an entrepreneur?

This series/post is brought to you by Gillette. Learn more about Gillette and its products at