Why I wear the same thing every day

There have been many articles written about wearing the same thing every day. It’s not uncommon to see it listed as one of the ways to optimize your performance in various publications like Inc. or Forbes. It makes for a catchy title — “Follow these 5 steps to live like a billionaire”.

The reason typically given is that it reduces the amount of decision fatigue in your day. We all have a limited capacity for decision making and therefore limiting even the smallest decisions gives you a greater capacity to focus on the most important choices later in the day. I think this has definitely played out in my own experience, but it was not the initial motivation for me.


First, what do I mean that I wear the same thing every day? Here’s the uniform:

Blue button up dress shirt
Levi 501 Jeans
Allen Edmond’s Chili dress shoes
Charles Tyrwhitt Slim fit non-iron puppytooth sky blue shirt

I cycle through about a half a dozen blue button up dress shirts. After a few years of doing this I’ve landed on a single brand and a specific fabric. They are nice so they last and don’t have to be ironed every day. I figure a shirt lasts about two years if I’m cycling through seven in the closet.

I have 2 pairs of Levi 501 “Shrink-to-fit”. I’ve tried to find something simple that won’t change too much and is always available in a color I want from Amazon. They aren’t very fancy, but work for my day to day environment which includes startup office, motorcycle commute, occasional “tech” business casual events, church, and date nights with my wife.

The final piece is a pair of Allen Edmond’s Chili Fairfax. I bought the first pair 2013 and they are still going strong (that’s about 1,250 days). They’ve been refinished once with rubber soles. I now have a few in rotation so they last longer.

I don’t think this combination will change for a very, very long time. The reason why has as much to do about how I got here as it does the final result. First, I’ll run through the history of how I landed here and then summarize how this has benefited my life day to day.


This all started with two key components from my youth. First, we were not a very wealthy family. It’s hard to know exactly how tight things were, but we shopped thrift stores, Aldi, and drove vehicles that were always at least 10 years old. We never went without, but compared to the Christmas presents most families got their kids it felt like it. That lead to one key element in this story — we shopped at Goodwill. I hated it. I’m not sure why, but I was very self conscious about how I looked at school. I’m not sure if it was because I knew that I was wearing $2.50 slacks from Goodwill or because they actually were out of date. Probably a bit of a combination of the two, but either way, it always felt like the most difficult part of my life at the time. I was a good student, a decent athlete, and had great friends, but deciding what to wear in the morning was a mess. Between not wanting to wear the same thing twice in a row, not having more than a few things that I was really comfortable with, and being hyper aware of my situation in the fashion pecking order at school, it was stressful.

As a quick detour, I want to point out that I’m not saying any of the above feelings were right or justified, but for some reason, they were very prominent. I was very blessed to live in an intact family with parents who loved and cared for me and did whatever they could to provide. I had it good.

Ok, so how does all of that lead to being the most boring dresser in the world? Well, the saying is true

“the apple doesn’t fall far from the tree”

I picked up my Mother’s wonderful affinity for Goodwill sometime in college. The funny thing was that it wasn’t about money for me. Well, ultimately it was about value, but not the absolutely requirement that I save money. I was getting into backpacking at the time and began to really like brands like Patagonia, REI, Northface, Marmot, etc. One day while at the Goodwill in Crawfordsville, IN, I found two pull over fleeces that literally changed the direction of my clothing perspective forever. They were awesome. They were both from The Gap. Nice, but nothing to write home about. But the excitement of finding a $60 product for $1.50 (half price day) was awesome.

After I graduated I started working at a startup and even though there was no dress code at all, I still felt all of the same pressure when picking clothes for the day. I was sick of it. And now I had time and money. Mainly time. I spent a lot of time at Goodwill. My roommate and I got addicted to finding deals at Goodwill. We lived in an area that was really wealthy so there were many good used clothes. We bought suits, shoes, and lots of shirts. During one trip he and I returned with over 30 shirts. Brooks Brothers, Bacharach, Lands’ End, and Joseph A. Banks. I got really used to wearing dress shirts. Initially I wore all different colors, but began to notice big differences in the nice brands vs. the cheaper ones. Then I landed two blue shirts. One Brooks Brother’s and one Lands’ End. Both were fantastically wrinkle free. To this day, I’ve not owned a shirt that came out of the dryer looking as good as these. I’m not sure if it was years of dry cleaning or just a fluke, but they were both awesome. Particularly the Lands’ End shirt. I remember fondly being able to wear that shirt and feel confident no matter what. It was cheap, low maintenance, and I got compliments. I started wearing it frequently.

Then the elbows ripped…

I was seriously bummed and ready to solve this problem once and for all. So I bought three of the closest shirt I could find from Lands’ End. They were good. They were about the same color as the original, fit well, and were well made. But they weren’t wrinkle free. They were labeled as such, but they still came out with little crinkles everywhere. The shirt from Goodwill looked like it had been pressed by the ironing trainer in the Army. Either way, I was now wearing blue shirts every day.

About the same time, I found a pair of casual dress shoes at Goodwill that I was wearing every day and had lasted for about a year. I bought the exact same shoes brand new when the old ones wore out.

The rest has been slow upgrades and iteration. I eventually committed to Charles Tyrwhitt dress shirts after a stint with Brooks Brothers and landed on Levi 501’s as a nice, consistent jean fit after years of too much variance in Eddie Bauer options.

The final step were the shoes. This is the second part of my experience growing up that informed my final attire combo. My dad was an insurance salesman when I was growing up. He worked his tail off to establish himself in a business that required relationships and for better or worse depended on first impressions. When you’re going door to door to thousands of houses and businesses, anything that can raise your close rate by a few percentage points is worth it. So, he bought two pairs of Allen Edmonds. He bought them in 1989 and I was still wearing them in high school around 2001. I never really realized how nice they were and how well he took care of them until I started searching for a nice pair of shoes myself. Once I finally decided to upgrade, I went directly to AE. I found a pair of seconds at Nordstrom Rack. They made for the perfect first pair. Great color and not too fancy so they would work with jeans.


  1. I absolutely have more capacity and energy for hard decisions. This is not understated. The impact has been so significant to me that I’ve applied the same principle to other simple things like the parking spot I chose at work every day.
  2. I am confident in what I wear every single day without any hesitation. This should probably be first. It is the single most important reason I do this.
  3. I save money. This might seem odd considering I’m buying fairly high quality products. If you saw the lack of other clothes in my wardrobe, you’d understand this vividly.
  4. I am not (as) involved in the rampant consumerism that is the American economy

Decision making

In The Power of Habit Charles Duhigg talks about how critical habits are to our ability to be efficient and effective in work and our personal lives. Habits not only help us be consistent, but they actually move mental load into basal ganglia. This frees our decision making portion of the brain, the prefrontal cortex, to focus and have the bandwidth to make other decisions.

Anyone who knows me really well, probably knows I’m not a naturally disciplined person. In fact, habitual would be the last word to describe me. I’m sporadic and distracted and more likely to chaos than order. This is why simple habits like wearing the same thing, or parking in the same place, or having a simple routine for getting into and out of my car help me so much. They take things that can be a major stressor for me because of my scattered brain and help shove all those little nagging decisions into the basal ganglia where I don’t have to think about them. My prefrontal cortex feels so active sometimes that it quite literally hurts. Anything I can do to reduce the neurons firing around that area of my head is a relief.


It is easy to gloss over this. If you’ve never felt stress or lack of confidence in what you wear you are blessed. I’m sure this varies from individual to individual, but for me, this one thing has had a huge impact on my life. So much so that it is hard to remember the feeling at this point. It has been so long since I’ve worried in any way, shape, or form about what to wear on a normal day. It is possible some of this is simply due to maturity. I’ve gotten married, had three children, and changed jobs 4 times in the timeframe that this wardrobe formed up. But I still think I’d be pausing every morning to make decisions if it weren’t for this.


I love finding things that have long term value. Some of my most cherished items are those that cost a little extra on the front end, but will last for much longer than alternatives. Everything from the $50 Seiko Watch I wear that requires no battery and has a timelines design to a $10 knife that I use in the garden and for grilling. There is something really appealing about the simplicity of things that aren’t disposable and will last for a long time. It pits two pathologies of mine against each other — my lack of order and organization against my extreme angst over losing things. One forces me into conquering the other. I take care of things and cherish them and KEEP THEM ORGANIZED so I don’t lose them.

The wardrobe is the same. I polish my shoes carefully and use rubber overshoes when it is raining or there is snow on the ground so that they last for a very long time. I change after getting home so I don’t get my shirts or jeans dirty. Simple habits that make the investment pay off both mentally and financially.


You might think that this one is odd. How am I not participating in consumerism? I’ve linked to at least a half dozen amazon products in this article alone. It is quite simple. I don’t obsess about it. I don’t envy what others have. I don’t feel the need to have the latest. I have a watch I’ll give to one of my sons. I have a leather bag that they’ll fight over when I die. I have a pocket knife my wife gave me eight years ago. I’m not saying I never desire something I don’t have, just that making slow, intentional decisions really suppresses the excess of our culture and helps me stay focused on things that really matter — relationships with family, friends, and time spent using things instead of buying things.