Entrepreneur Clothes

The Entrepreneur’s Wardrobe

I just spent an insanely, stupid amount of time getting dressed this morning.  The amount of time and energy I wasted pacing back and forth, from my closet to my mirror, trying on different shirts, pants, and shoes is depressing and infuriating. I’m now anxious and my blood is starting to boil at this seemingly trivial problem.

I’m too busy changing the world to worry about clothes.

As an entrepreneur, my commute is about a 500 yards down the road to a local coffeeshop. So, I have zero people I need to impress. Although, I am deathly afraid of looking like a bum, or even worse, being the smelly guy who just rolled out of the bed, or came from the gym.

This is all I thought about on my “commute” to work today; and now I find myself therapeutically venting on my blog, in hopes of finding a solution.

Mark Zuckerberg and Tim Ferriss have talked about this very issue. Too much of their valuable energy was being wasted on what to wear in the morning. That’s why, in case you haven’t noticed, they wear the same thing almost every single day.

When asked about why he wears the same clothes everyday, Zuckerberg said, “I really want to clear my life to make it so that I have to make as few decisions as possible about anything except how to best serve this community.”

My closet is filled with bullshit I never wear. Just fancy crap that looked great in my mind, or pretty swag on a mannequin with half my waste size.  I have blue crap, red crap, green crap, big crap, and small crap. Again, most of which I never wear.

Watch out for those bullshit pins on mannequins

This reminds of of Hick’s Law, a marketing law that I’ve preached to employees and clients for 10 years. Hick’s Law basically states that the more options you have, the harder it is to make a decision.

Damn! My closet is filled with options, most of which I hate.

Step 1: I need to Purge

I need to put all the shit I don’t wear into a pile and donate it, or throw it away. Not 20% of my clothes, I’m thinking 80%, gone.

I can almost feel the weight being lifted off my shoulders already. I can’t wait to get home!

Purge Complete!

Step 2: Define my wardrobe

What do I really like to wear? And be honest, Marvin. Don’t bullshit yourself.

Well, jeans go with almost anything.  They’re extremely comfortable, and unlike sweatpants, they socially acceptable almost everywhere.

I also like very dark long sleeve or short sleeve shirts. This includes dark blue, charcoal, and black. That’s it. No other colors. I don’t look fat in dark clothes, and they always go with jeans.

Socks and shoes.

I hate socks and I hate shoe with laces. I’d wear Toms everyday of the year if I could. The only problem is that I live in Chicago, and come December, my Toms won’t stand a fighting chance against the horrors of Chicago slush.

I need to find simple winter shoes that can easily slip on and off, similar to Toms. Got it.

Step 3: Stock up

I know what I want now, thus I know what i need. So, I need to stock pile. I need to take a trip to the store, and stock pile a bunch of the same shirts, same jeans, and same shoes.

I have a few t-shirts and long sleeve shirts that fit my goal now, I just need more of them. I need to buy 8-10 of the exact same shirts, and I need to buy 3-5 of the exact same jeans and the exact same shoes.

Forget colors, forget different styles. Let’s keep my morning super simple and super efficient. I’ve got more important things to worry about.

My new wardrobe:

The Entrepreneur’s Wardrobe

One last thing…

I really think simplicity is the future. After all, “simplicity is the ultimate form of sophistication”, according to Leonardo da Vinci. I see a future without labels. No Gap or Old Navy logo across our chests. No LV logos on purses, and no swooshes on shoes.

We’re stressed out because we’re walking advertisements, and we don’t even know it. We’re making too many unnecessary and unimportant choices, and it’s killing us. Well, it’s killing me.

Off to the store.

Thanks for listening.