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.
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.
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.