Steve Jobs is so famous for his black turtleneck look. So is Mark Zuckerberg with his plain t-shirts. In case you were wondering why they like wearing the same thing everyday (or at least every time they have an audience), it’s because of the hassle most of us feel on the daily. What on earth am I going to wear? Why do I even care? 

It’s simple. At a certain point we stop dressing up for fun and we start to care. We learn that we can communicate with our style. We can perceive someone’s mood and even guess their income by just paying attention to their outfit. Our clothes start to reflect our taste. And how we choose to wear them or how well we desire to present ourselves will start to show who we are. So we start to obsess on what we should and shouldn’t wear. What message are we sending? Are we overdressed? And spoiler alert, the questions never end. 

Some of us start to notice the power we have. The power to control our image and use our outfits as masks to get what we want. Celebrities use it to make sure their fans know how much better they are than them. Even politicians know this and use it to their advantage. And well, the billionaires figured it out too. They can certainly afford excellent stylists to communicate exactly what they want. But instead of weaponizing it, they seem to have eliminated it all together. Late Steve Jobs was famous for his black turtlenecks because he liked the idea of uniforms. 

I remember my high school had uniforms. It was common for schools to have uniforms. Because if you don’t have to worry about what you are wearing, or if you are not spending time looking at what other people are wearing, you can focus on your studies. Now billionaires do it so we won’t spend time judging how they look. They don’t even want to give us the chance to judge their personalities based on their taste. Even Silicon Valley’s fraudulent billionaire, Elizabeth Holmes, used the same trick. We are quite sure it stemmed from her obsession with Steve Jobs but it was still a uniform that she chose to wear. Ironic isn’t it? 

We usually don’t get to choose our uniforms. And unless you are a billionaire, you probably won’t be able to get away with wearing the same thing everyday. It would just raise more judgements. And as much as we don’t want to give a rat’s behind, we tend to care. Which brings us back into the loop. To wear or not to wear?