A friend of mine recently had the chance to meet a musician he admired at a workshop. Upon meeting him, my friend texted me this statement: “He’s such a big deal, he wears sweatpants to these workshops!”
I responded in the only way I knew how, which was to address this huge assumption about what we would all be wearing if we were no longer trying to prove anything to anybody.
I asked him, “Is this what you aspire to? A life of sweatpants?”
We then agreed that possibly the true show of “making it” would be to just be naked, all the time. Or would it? I tried to think about myself, living my dream life of sewing at home, hosting dinner parties and playing music. Would I really ever be happy wearing sweatpants all the time? Maybe cute sweatpants. More likely, party dresses. To be honest, I find myself already wearing these things on a regular basis; I think for the most part I am wearing the clothes I aspire to wear, because they fell like a true representation of the life I live and want to live.
I know I’m not an “Average Joe,” so I began to take survey of famous people and how they dressed as they reached the height in their careers:
Steve Jobs
Steve Jobs famously wore a black turtleneck, jeans and gray, New Balance sneakers every day.
Some say that this was Steve Jobs’ way of eliminating the trivial decision making that goes into picking a unique outfit each morning. Maybe this is true, but I would argue that Steve Jobs actually carefully chose this uniform to be the purest form of self expression for him and stuck with it because he felt like it presented him in the way he wanted to be seen and the way that he saw himself.
Steve Jobs wasn’t born wearing a turtle neck and jeans (as far as I’m aware). And if you look at some past photos of him, you can find him wearing a variety of clothing, from blazers & bow ties to striped sweaters and jeans. Steve Jobs, during his early years, was like any of us: occasionally donning a fancy suit because that’s what was expected of him.
But when Steve Jobs returned to Apple in 1997 the iconic photos of him in a black turtleneck, wire-frame glasses, light colored, relaxed fit jeans and gray New Balance sneakers begin to arise.
Sure, he seemingly always had wire frame glasses. And sure, you can find some vintage photos of Steve Jobs in a black turtleneck with shaggy hair and possibly no shoes. But the combination, the repetition. To me, this iconic outfit choice represents a honing in of values and choices for Steve Jobs. It represents the moment that he figured it out and decided to say, “this is who I am, this outfit is a reflection of my values and the company I represent.”
The repetition, then, is more happenstance and less about eliminating choices. When you figure out who you are and who you want to be, why would you choose to dress any differently?
Francis McDormand
Francis McDormand is famous for not following “the rules” of the red carpet. While Hollywood starlets borrow expensive jewels and designer gowns, Francis McDormand does what she likes, including wearing (custom) yellow, suede, Birkenstocks with her pink, Valentino gown, as she did at the 2019 Oscars.
For someone like Frances McDormand, no longer dressing to fulfill other’s expectations doesn’t leave her wearing the same jeans, graphic tee and tousled hair everyday. Instead she consistently defies our expectations by sometimes dressing up, sometimes dressing down but always looking impossibly cool in whatever she wears, because she wears it with with an air of edgy confidence one can only gain by truly accepting and being comfortable with the person that they are.
In Summary
While I researched Steve Jobs for this blog post, I read a lot of articles pointing to other successful men who always wear the same thing, like Barack Obama or Mark Zuckerberg. The articles stressed the idea of eliminating choice from your wardrobe to help you focus on more important decisions. I don’t disagree with this idea (as a woman who owns the same skirt in several colors), but I think the bigger picture that none of the articles got to is how to choose your ideal, daily, uniform.
Mark Zuckerberg didn’t don a blue-gray t-shirt and a neutral hoodie because he was trying to dress like some other Silicon Valley bigwig. He wore it because it felt like him. It felt comfortable, it implies youth and a hint of rebellion against the idea of having to dress up to be taken seriously. Mark Zuckerberg’s outfits are uniquely his, but also not all that unique at all. Any of us could choose to dress like Mark Zuckerberg if we chose to. But would it be the right choice for you?
To really “make it,” in our lives, our careers, our happiness, doesn’t that just mean that we fully become the person that we are trying to become? And, ideally, as this person we are also learning and growing and reacting to the world around us, so we should leave room in our wardrobe choices for spontaneity, .
My one piece of advice as you find yourself honing and curating your ideal uniform, whether it be limited to blue-gray tee shirts and hoodies or an eccentric mix of jeans, gowns and Birkenstocks, is to just make sure it makes you feel happy, comfortable, inspired and confident. Mimicking the outfits of other famous, successful people eliminates the most important part of this equation- YOU! And YOU should be the showcase of whatever outfit you don.
