Dyed hair, ripped clothes, lots of tatoos and makeup used to be deemed as unprofessional attire by many industries for years but we’ve come a long way and in 2021, the world, especially in high tech and startup culture, is here for this medium of self expression. So, this article won’t focus on the repetitive jargon of what your clothing says about you, because that doesn’t matter. Nor will it be intended for the fashion forward audience because you already got this, effortlessly. But for those of us, like me, who struggle to even maintain an appropriate closet full of clothes, this article is for you.

Learn from my strategy for staying sane and being productive in the ‘what to wear’ department.

Intro: Scenarios for Dress

I've identified three unique areas of dress: 1. Work 2. Casual 3. Social

Generally, what one wears to work does not always work for casual settings, and neither work or casual clothes always fit social events and occasions. Sometimes there are overlaps, but sometimes there are clear social norms of which outfit to choose.

Solution 1: Same Thing Everyday - The Dilemma

What I thought was the easiest approach towards maintaining an easy dressing routine, which I did earlier in my career, was to wear the same thing every day; grey jeans and a charcoal hoodie with a t-shirt underneath. I had around 9 pairs of the same jeans and my hoodie. This method worked for me, I didn’t need to think. Just put on the same fit I had on yesterday (clean version, of course). But I progressed in life, and in my career and began networking which meant social functions became way more relevant.

I was acutely aware of how my ‘all purpose’ jeans and hoodie might negatively impact my social appearance, especially with girls. So, I decided to do the right thing and go shopping for additional pieces I could wear out. I ran into a few problems though. Finding clothes that fit well was a big one. Standardized sizing does not translate well to comfort and fit for every person. Sometimes you find your size and it fits like a glove but many times you find your size and you're sweating trying to pull your arm through its sleeve.

My second issue was that whatever I did add to my wardrobe never seemed enough, quality-wise but also, quantity. I needed more clothes because I was attending many different kinds of events, from social Galas supporting a charity to client meetings and yes, dates.

Solution 2: Dillema Phase 2

As I continued to add a plethora of dress clothes to my closet, I finally reached the perfect quantity. Something like eight different pants and eight different shirts. For my day to day though, I carried on with the same hoodie and jeans.

I liked my closet, it was a great balance containing everything I needed, or seemingly needed. But then something unexpected happened. The social events I was getting invited to started to become more casual. Looking at both sides of the closet, I decided to stick with my hoodie and jeans to attend these in the middle affairs.

“Hey Charlie, you wash your clothes right!?” friends from these events would jokingly say.

Nervous Laugh

I was just some ambitious person trying to stay focused on my goals, but the unwanted attention seemed to interfere. If I had to mentally prepare myself every day for the potential onslaught of, "thou are different" then what mental energy did this approach save in the end? This was compounded by the fact I started hitting the gym at this time, and my clothing again stopped fitting.

Solution 3

I like jeans and hoodies the best and now some clothing I was wearing I actually didn’t even enjoy wearing. I wore clothing for other people, or for the way I felt how other people perceived me whether it was real or not.

I went back to the drawing board, in other words the mall, and started to get myself a wider variety of jeans and hoodies, different colors, shapes, and brands. I wanted to wear the same clothing everyday to sidestep the mental energy I needed into excogitating what others may think. Ironically though, I started to care less of what others thought and continued to just wear the clothes I liked and enjoyed wearing.

At the end of this saga, I had an A-team wardrobe of dress clothing, casual clothing and some things in between. Needless to say, this whole trial period was expensive. One of these days, down the line, if and when my professional life becomes more stable, as well as my social life, I will consider going back to my closet and re-strategizing as new opportunities come my way. However, at this stage in my life, the ideal is having a variety of dress and casual clothing and articles that I enjoy wearing.

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.

Solution 3

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.