Unique Scenarios for Dress
I've identified three unique areas of dress: 1. Work 2. Casual 3. Social Functions
What one wears for work, usually will not work for casual settings, nor will either work for social functions. For the ambitious individual, looking to create some sort of routine with clothing, it can be challenging. This is what I have developed in order to create some sort of sanity around clothing.
Solution 1: Wearing the same thing everyday - The Dillema
The easiest approach towards this one, which I did earlier in my career is wearing the same thing every day. It was grey jeans and a charcoal hoodie. I had something like 9 pairs of the same clothing. This was great, the issue is that as I progressed in life, and in my career, this became problematic in social functions. I was acutely aware of how this might negatively impact my social life, especially girls. The second issue is that I never found the perfect piece of clothing. This one was either too tight around the calves, this one was either too loose around the waist. I found myself buying clothing, but then being frustrated with how it felt, comfort-wise. The third issue, is that even though I ended up getting more clothing for social functions, I found it wasn't enough, due to the increased level of social functions. This plan, while noble in design, was an absolute crapshoot. Something I decided we better fix, quick!
Solution 2: Dillema Phase 2
I started to add a plethora of dress clothing to the array. Something like eight different dress pants, and eight different dress shirts. I found that was enough for social events. For my day to day, when there wasn't a social event, I ended up still keeping with the same hoodie and jeans.
However, then something unexpected started happening. Social events started to become more casual, and I still wore the same hoodie and jeans. People started noticing. "Hey Charlie, you wash your clothing right hehe(nervous laugh)?!" I was just some ambitious person trying to stay focused, but the unwanted attention seemed to defeat the purpose. If I had to mentally prepare myself every day for the potential onslaught of, "thou are different", what mental energy did this approach save in the end? This was compounded by the fact I started hitting the gym around then, and my clothing stopped fitting around then anyways.
So, then I started to get myself a wider variety of jeans and hoodies. I found, true, I like jeans and hoodies better than others, but I think I went through a personality change during this time. I started to care less about how I dressed, which ironically is the opposite of why those who wear the same thing every day do it. They wear the same thing every day, to side-step the mental energy they employ towards how others may think.
This led to the 3rd dilemma, which is, some clothing I wore, I simply didn't like. What ended up happening is that I only started getting for myself items that I truly enjoyed wearing. It was like the A-team fo dress clothing. However, this whole trial period was expensive, and honestly someone
One of these days, down the line, if and when my professional life is more stable, as well as my social life, I will consider going back to this strategy. However, in this stage in my life, the ideal is having a variety of dress clothing, and casual clothing. The important part is to make sure I enjoy wearing all articles of clothing, so it is not too mentally taxing.