denim personality (mini-📝 34/100)

I’ve been getting really into fashion lately. Perhaps my visit to New York was what really kicked it into overdrive for me given the opportunity to get inspiration everywhere you go on the street, but I’ve always been enamored with the idea of fashion and making yourself look good to feel good. As a child, I was bold with my choices. According to my dad who resurfaced an old journal entry recently, I once tried on some shoes in a store and refused to take them off because I was so enamored with them, and my parents ended up having to buy this nice pair of shoes for a 5-year-old (what a difficult child I must have been 😅). I’ve always tended to be reserved in my choice of presentation, sticking to the popular styles and shying away from experimentation with pieces or styles that caught my eye. I’m trying my best now to unlearn that old habit and embrace that playful side of mine. To that end, I’ve been challenging myself to try a new fit every day to explore my style and force myself to try new combinations that are less “safe.”

early to the denim trend, even got the smolder down

a fit from NYC

I remember when I was in my pursue-prestige-at-all-costs phase in college grinding for a good tech job and I watched a video about how the most successful tech CEOs minimized their decision-making consumption by eliminating unneeded daily decisions. One such decision is what you decide to put on in the morning. Many chose to adopt a daily uniform to automate this process. You probably recognize Steve Jobs and his black turtleneck and Mark Zuckerberg in his grey t-shirt. I recall an intense sensation of cognitive dissonance when I came across this concept. I wanted to be willing to sacrifice everything for the dream life I pictured—making a difference in the world at a well-known tech job, but it felt wrong to be giving up a tiny thing that gave me joy every day. I wondered if happiness was part of the deal, whether your obligation to making an impact meant giving up on your own desires.

Steve Jobs and Mark Zuckerberg rocking their signature outfits

A couple days ago I stared watching Naomi Osaka’s Netflix documentary. It starts by charting her explosion into stardom in tennis and how she grew into it. Besides tennis, her other passion is fashion. In the documentary, she laments how athletes usually don’t get to dress up and are told not to care for fashion because it’s a distraction from the craft. Sound familiar? Naomi didn’t let that dissuade her from wearing fits on the court or collaborating on collections with some of the most renown companies and designers in the scene. Perhaps it’s because she’s used to having to burst barriers and trounce on expectations in order to get what she wants. There’s a hardline determination and hunger to get what she wants, and no one telling her otherwise is going to stop her. It reminds me of the “dauntlessness” and “intensity” used to describe Omar Sy in his repeated career suicides. You need that unfailing courage in order to fly against what the “experts” and gatekeepers in the field demand of you.

I only hope I can emulate that dauntlessness in the face of greater adversity. After all, why give up a piece of yourself for a group of people that don’t care about you?

from Naomi’s website

It seems like regardless of where you go or what craft you choose, successful people will tell you the right way to do things and which things are right and which others are wrong, which way is up and which way is down. There’s an attitude that some things are useless and others are essential. And then the rules get broken by some upstart newcomer, and the world has to find itself again.

Fashion feels integral to my personality. It’s a representation of how I’m feeling, of what emotions I want to convey, of the version of myself I want to be. Wearing a uniform every day tells me you prize efficiency and practicality. Experimenting with mixing formal wear and streetwear or loud colors and patterns tells me you embrace playfulness and love the thrill of the new. I feel like every time I try a new out-there combination, I uncover a buried piece of my soul, a piece of that child who knew what he liked and wasn’t afraid to shout it to the world.


This is the 34th installment in my experiment of publishing raw, lightly edited mini-essays every day towards achieving 100 public pieces. Check out the rationale and the full list here or view my evergreen, longer pieces on my website.