The Taste and Skill Gap in Fashion

An idea that I’ve wrote about a few times is the gap between taste and skill. As a creative, this gap always exists; it’s part of what motivates us to get better but also frustrating because taste and skill are asymptotic. Your skill will never be as good as your taste.

Fashion taste can evolve quickly these days. We’re constantly exposed to fashion through social media and other daily influences. What’s frustrating about fashion os that your styling skills are only as good as your wardrobe. Without the right pieces, you won’t be able to fully execute the looks you envision.

Fashion enthusiasts are driven by a constant desire for new clothes. As their tastes evolve, they may seek to improve their styling, but the underlying motivation is the pursuit of acquiring novel garments.

July 19, 2024

10 Things I Learned About My Personal Style This Year

In a previous blog post, I wrote that building a wardrobe takes 5-7 years. This is because it takes time to develop a personal style, and then to find pieces that match that style.

Developing a personal style is a process of trial and error. I may think I know my style, but then realize I don’t like certain pieces I’ve bought. Or I’ll try on something that isn’t my typical style, but I end up liking how it looks on me.

This year, I’ve learned a lot about my personal style. Here are 10 learnings:

  1. Three words I’d use to describe my style are subtle, elevated, and contrasting.
  2. I’ve worn slim-fit pants for years, but after trying different styles, I’ve found that regular-fit pants with a high waist are my favorite.
  3. I prefer relaxed-fit button-ups, oversized sweaters, and slim-fit t-shirts for tops.
  4. Collared shirts > T-shirts.
  5. I don’t need to stick to my size”. I would always buy tops in a mens small but since sizing isn’t standardized in the industry some pieces look better on me in a size medium or large.
  6. Boots, Loafers, Derbies > Sneakers.
  7. Indigo is my favorite color.
  8. Much of my style inspiration comes from Japanese fashion. Many of my favorite brands are based in Japan like Kapital, Momotaro, and BEAMS.
  9. My style most closely aligns with Drew Joiner. He’s also my favourite fashion creator right now.
  10. The story of a brand and a piece is just as important to me as the aesthetics.
July 18, 2024

Living a Rich Life Outside of Work

My friend who recently visited New York City remarked that everyone seems to have a side hustle. We all have our regular jobs, but we also write, paint, or DJ in our free time.

I was talking with my friend, J, and after knowing her for nearly a year she asks me, So James, what do you for a living?”

I have a few close friends whose jobs I’m unaware of.

I don’t actively avoid discussing work with my friends. We live rich lives outside of work and the topic of work just doesn’t come up.

July 17, 2024

Make Space to Miss It

Two months ago, I was going through a tough breakup and I had an OTWC event that I was hosting on the upcoming Sunday. Despite my personal struggles, I wanted to put on a good show for the community members who had already signed up to attend.

And I’m glad I did, that event was a reminder of why I host the OTWC. During this session, I wrote one of my favorite pieces of the year - a short personal piece describing the emotions I was feeling at the time. I was also surrounded by the love and empathy of the community, something I was grateful for at the time.

Organizing the OTWC isn’t easy. I often doubt if I’m built” for this. Yes, it’s stressful, it’s time-consuming, and I’m often anxious about our next event. Yet, I find so much joy in organizing the events, serving the community, and meeting other writers. The joy far outweighs the pain.

We’ve been on pause for the past few weeks and it’s during our breaks that I’m reminded how much this community means to me. I wouldn’t trade it for anything.

July 16, 2024

OTWC is Back to Weekly

This is a cross post from OTWCs Substack

For nearly two years, we hosted weekly writing events in the city.

Earlier this year, we made some big changes, one of them being the transition from weekly to monthly events.

During that time, one thing became clear: the weekly cadence is an essential ingredient that makes OTWC special.

Sometimes, giving space allows you to appreciate what you miss.

It’s time to bring back what works.

Starting on Sunday July 28th, OTWC is back to hosting our weekly writing sessions.

Join us every Sunday morning throughout the rest of the Summer.

RSVP for our Season 3 Kickoff here.

Hope to see you there!

July 15, 2024

How I Got into Fashion

Back in elementary school, the popular trend was big, bulky, and colorful G-shock watches. For my birthday, my parents got me one. It was a black G-shock that was bigger than my pre-teen wrist with red accents loaded with features I didn’t need like the moon phase and tide graph. I loved it.

I broke necks the first day I wore it at school. One of the popular kids asked if he can borrow it for a period. My status instantly elevated to that of one of the cool” kids. As a status-conscious, insecure, teenage boy, this is when I started associating dress with status. I wore that watch daily for the rest of the school year. And this mindset continued throughout high school and early university.

My university had strong engineering and computer science programs so naturally I gravitated towards a career in technology. One unique characteristic of the tech industry was the lack of a formal dress code. Many of the most prominent figures in tech famously flexed their minimalist wardrobes. Steve Jobs with his signature Issey Miyake black turtleneck, medium wash Levi’s 501 jeans, and gray New Balance 992. Or Mark Zuckerberg with his daily uniform of a tee and jeans which he says reduces his cognitive load in the morning. Tech was seen as anti-elite. You couldn’t judge someone by how they dressed because they could be building the next big unicorn.

Embracing the tech uniform gave me permission to not care about what I was wearing. I thought it was refreshing. I thought this was how it should be. No one else around me cared either. I traded much of my wardrobe for plain basics - white sneakers, t-shirts, and pants.

I started to dress and look like everyone else.


My style remained largely unchanged in my late teens and early twenties.

Then in early 2020, I had a conversation with a friend that became the catalyst for my fashion journey. I was back in my hometown and I bumped into an old high school friend at the gym. We haven’t talked since senior year of high school and the first thing he says to me is, James, you look exactly the same.”

The last time we talked, I was 16, I was still a kid. I was 22 now. Internally, I grew so much. Externally, I looked the same. My friend likely assumed that because I looked the same, I was the same.

My friend’s comment made me realize there was a disconnect between my self-perception and how I expressed myself through how I dressed. Ever since that day, I became hyperaware of this gap.


In the Summer of 2022, I was celebrating my one-year anniversary in NYC. I’ve been working full-time now for a year now so I had some disposable income. It was then that I decided that the timing was perfect.

During that Summer, I became a student of fashion. I donated 90% of my wardrobe and built it up from scratch. I bought textbooks, courses, and discussed this with my friends in the industry. Living in New York City, one of the world’s fashion hubs, I was constantly inspired by the outfits I observed on the subway, in coffee shops, and while walking throughout the city. I viewed every clothing store as a classroom and engaged the sales associates as if they were professors, asking them questions to expand my fashion knowledge. Every day I was learning something new.

Fashion is a cultural language that I was becoming fluent in. It’s an art that everyone participates in every day. What you wear reflects who you are and the best part is you can choose to be whoever or whatever you want. You can use your clothing as a canvas to express yourself — show different styles, tell a story, or represent your personality.

My style is my story. It’s a reflection of who I was, who I am, and who I want to be. In the past, I was an engineering student, a musician, a breakdancer, a Torontonian. Currently, I’m a Technologist, a Writer, a Filipino-Canadian, a New Yorker. To craft a stylish wardrobe means to infuse my story into the different pieces, I want to honor my roots, and dress like the person I want to become.

July 14, 2024

Make Your Writing Sing

I’m often asked what makes great writing.

One overlooked aspect is rhythm. It’s making your words sing in a way that engages the reader.

The above example from Gary Provost illustrates this beautifully.

July 13, 2024

You Don’t Need to Read

In a 2015 interview, Kendrick Lamar was asked if he reads a lot. Here’s his response:

Naw-uh… I’d rather be interacting with a person than gathering up information from somewhere else. [I’d rather] speak to a person with wisdom that’s been here before me.

Kendrick Lamar was the first hip hop artist to win a Pulitzer. Given his complex lyrics and the subject matters he raps about, I assumed Kendrick was an avid reader. It turns out that’s not the case.

If you live an interesting life and surround yourself with interesting people, you don’t need to read. Personal experience is enough.

July 12, 2024

Blue Collar and White Collar

Blue chambray shirtBlue chambray shirt

The term blue collar refers to manual laborers while white collar refers to knowledge workers. But where do these terms come from?

Blue collar refers to the blue-colored denim or chambray shirts commonly worn by factory, construction, and other types of manual labors. These shirts were durable, easy to maintain, and the blue collar concealed dirt and grime.

White collar comes from the white dress shirts worn by professionals who work in an office environment.

July 11, 2024

Just Spend 5 Minutes

Want to write more? Spend 5 minutes tomorrow writing on your notes app.

Want to read more? Instead of looking at your phone while waiting in line, crack open a book and read for 5 minutes.

Whatever habit you want to build. Whatever skill you want to learn.

Just spend 5 minutes.

It all adds up.

July 10, 2024

Fall Down Seven Times, Get Up Eight

Failing is a natural part of any dream worth pursuing. Part of the fulfillment and joy of the journey is pushing yourself beyond what you are capable of. But that also means you’ll fail. And you’ll fail a lot.

Nana korobi, ya oki is a Japanese proverb that translates to fall 7 times, get up 8. It embodies the spirit of perseverance, persistence, and resilience necessary for any journey.

I fell a few times this year. One I’m still getting back up from. But from these failures I learned where I need to grow, I learned humility, and I learned more about myself.

July 9, 2024

What to do when the party is dead”?

My friend, Ethan, told me a story worth sharing:

During my last night in Rio de Janeiro, I planned on meeting up with some hostel friends at a nightclub. I arrived past midnight, and they were already there. They were complaining about the vibes and atmosphere at the club. My friend told me that it was dead in here.”

Feeling inspired in the moment I gave a pep talk; If the party is dead, you have two choices: complain about it or turn it up.”

Prior to entering the club, I was present, I was grateful, and I was ready for an amazing evening. The fact that the club was dead” did not stop me. I went on the dance floor, I felt the music, and I moved how I felt like. I didn’t consume alcohol to get drunk, but to feel energy and excitement. I was living in the moment. I was in a state of euphoria and I wanted to share my energy with those around me. Eventually, my friends joined me, strangers joined in, and we all danced together. The club came to life. It felt like a dream.

I had one of the best nights of my life, we all did. To become the life of the party wasn’t my aim. My only aim was to be present, engaged, and share my energy with those around me. Becoming the life of the party was just a side effect.
July 8, 2024

On Repeating Outfits

From the Lizzie McGuire movieFrom the Lizzie McGuire movie

If I’m going to a function, and I know that at least one person has seen my fit before, the above dialogue plays in my head. In the fashion world, an outfit repeater is almost seen as a criminal offense. Then I realize I don’t give a fuck. No one else cares too if you’re wearing the same outfit twice.

Outfit repeater” is a result of the social media age and fast fashion. You don’t want to be seen on social media wearing the same outfit and fast fashion has made it easier than ever to have the trendiest, newest piece, for next to nothing.

The irony is that some of the most stylish people wear the same outfit daily. To have a daily uniform is the apex of having a signature style. It shows self awareness and confidence in their own style. Rick Owens, Bill Cunningham, and Karl Lagerfeld more or less have worn the same outfit for years, yet no one calls them an outfit repeater.

I too have little desire to have a large wardrobe. I prefer a smaller wardrobe with high-quality pieces that I wear for years. This means that I do repeat outfits and I’m proud to do so.

July 7, 2024

Menswear is Functional, Womenswear is Form

Many menswear garments today are historically rooted in function. For example, denim jeans were made for the gold miners in San Francisco. Or chore jackets featured many pockets for French labourers.

Traditional womenswear, on the other hand, seemed to focus on form. Think of dresses, high heels, and skirts.

This is another example of how clothing is a mirror of the cultural zeitgeist and how gendered clothing reinforces stereotypes.

July 6, 2024

Less Goals, More Experiments

Whether it be writing, recruiting for a job, or getting ripped, I’ve proved to myself that I can repeatedly set goals and accomplish them. Each time I achieve a challenging goal, it boosts my confidence and reinforces my belief that I can accomplish any goal I set for myself.

This year, my focus has been on my creative goals, but I’ve tended to overthink and lack execution. What’s difficult about setting goals for my creative life is that there’s a multitude of paths I can take. There’s no right answer. Instead of focusing on goals, I’m shifting my mindset to an experimental approach. This means less overthinking, less goal-setting, and more trying out different ideas to see what works best.

July 5, 2024

On Having a Niche

One of the biggest conflicts in my creative life has been whether to niche down or not. Every playbook on how to grow an audience says that you need to focus on a niche to grow. My beef with this idea is that having a niche feels unnatural. We’re complex, multifaceted beings with a variety of interests. Why limit yourself to a niche?

I’ve seen it happen time and time again. A creator niching down and feeling stuck because they pigeonholed themselves. They become a victim of their own success.

But now I understand that I needed a mental reframing. I wrote a post the other day on newness vs nuance that has been living in my head rent-free. Beginners find novelty in newness, while masters find novelty in nuance. Writers like Matt Levine, Ryan Holiday, and Arnold Schwarzenegger have daily newsletters they’ve been writing for years about one topic. Matt Levine writes about finance, Ryan Holiday about stoicism, and Arnold Schwarzenegger about health and fitness. Especially if you’re genuinely curious about the topic, you can go infinitely deep into it and not run out of ideas to discuss. That’s how you focus on a niche in an authentic way.

July 4, 2024

Don’t Buy Retail

This week, I visited my local thrift stores after work. 

I first stopped by Crossroads Trading which is around a 5 minute walk from my house. I usually don’t have any luck at this store but this time was different.  I checked out their jean section and I was surprised by their selection. There were loads of pairs of Levi’s 501s and 505s, both are in style at the moment. But I also found 3 pairs of Acne Studios jeans and a pair of trousers from Bruno Cucinelli. The Acne jeans probably retailed for around 400$ each and the Bruno Cucinelli trousers probably were 800$ at the very least. All pieces were under 40$. While it was tempting, the style wasn’t what I was looking for. 

Then I hit the jackpot, I found a pair of Jil Sander+ Regular Fit Selvedge Denim jeans. I searched it up online and they retailed for $1200, here, they were only 60$. They were in perfect condition, the silhouette was exactly what I was looking for, though the waist was a bit loose. Nonetheless, I’m a sucker for Japanese denim, I had to get them. Right after, I brought them to Frank, my tailor, and he said he can easily bring in the waist for 40$. I basically got a pair of perfectly fitting Jil Sander jeans for 100$. 

I went thrifting again later that week to fill in the rest of my Summer wardrobe gaps. I found a Rag and Bone black button-down for $20 (retails for $250), a You Must Create camp collar shirt for $15 (retails for $200) and a vintage Ralph Lauren relaxed fit button-down for $20 (retails for $100+). 

Hauls like these are why I don’t buy retail clothing anymore. Almost 80% of my wardrobe is either thrifted or from vintage stores. Some of my favourite pieces in my wardrobe that I wear often I thrifted for like 5% of what it would sell retail. Not only is it significantly cheaper to buy second hand, but they’ll also be unique pieces that no one has, and buying second hand is more sustainable than buying new from retail.

July 3, 2024

Two Years in New York City

I live in New York City.”

On July 2nd 2022, I said those words for the first time.  

Two years later, I’ll still wake up in the morning, stare out at the Brooklyn sky, and remind myself that this isn’t a dream. I fucking live in New York City. 

Whenever I travel outside of NYC and meet someone new, one of the first questions they ask me is where I’m from. Last year, I would’ve said I was from New York but I’m originally from Toronto. On an earlier trip this year to San Diego and my recent trip to Europe, I just said I was from New York. I wasn’t consciously removing my association from Toronto, it was more subconsciously. Perhaps, that’s yet another milestone that I’m becoming more and more of a New Yorker.  

When does one become a New Yorker anyway? Is it when you start folding your pizza in half? Is it when you start pronouncing Houston Street correctly (it’s not Hew-sten)? Or is it when you start cheering for the Knicks in the playoffs?

Being a New Yorker is not a special badge given to you by the city’s mayor once you reach a certain milestone. If you live in New York, you’re a New Yorker. It’s that simple. 

I know this city better than any other in the world. It’s a city that I fell in love with and fell in love in. And the more I learn about it, the more I love it. 

I wrote an old post on leaving things better than I found it. I see living in a city as a mutual relationship. I can’t just live here and take, take, take. My time in New York has been incredible and I want to do what I can to give back. 

Here’s to another year in New York City 🍻

July 2, 2024

Read 100 Books About What You Do

There’s a saying that if you haven’t read hundreds of books about what you do, you are functionally illiterate.

Take for example a military general. A great military general can’t just learn through trial and error. The stakes are too high. One mistake may cost thousands of people’s lives.

Thankfully, most of us don’t have jobs where other lives are at stake, but the point still stands.

The problems you face aren’t unique to you, there have been hundreds, probably thousands of people that have faced similar problems in the past, and succeeded. And you owe it to yourself to learn from those that came before you.

July 1, 2024

It’s Not How Good You Are, It’s How Good You Want to Be

As a gift for one of my past internships, my manager gave me Paul Arden’s book, It’s Not How Good You Are, It’s How Good You Want to Be.”

When I first moved to New York, it was one of the few books I made space for in my suitcase.

Whenever I feel unmotivated, I turn to its first few pages and I feel the fire within me igniting again.

Here are a few excerpts from its opening pages:

Nearly all the rich and powerful are not notably talented, educated, charming or good looking. They become rich and powerful by wanting to be rich and powerful.

Your vision of where or who you want to be is the greatest asset you have. Without having a goal it’s difficult to score.

All of us how want to be good at our jobs, but how good do we really want to be?

Quite good. Good.

Very good.

The best in our field.

Or the best in the world?

Talent helps, but it won’t take you as far as ambition. Everybody wants to be good, but not many people are prepared to make the sacrifices it takes to be great.

To many people, being nice is more important. There’s equal merit in that, but you must not confuse being good with being liked.

Most people are looking for a solution, a way to become good. There is no instant solution, the only way to learn is through experience and mistakes.

You will become whoever you want to be.

You can achieve the unachievable.

Firstly, you need to aim beyond what you are capable of. You must develop a complete disregard for where abilities end. Try to do the things that you’re incapable of.

If you think you’re unable to work for the best company in your sphere, make that your aim.

If you think you’re incapable of running a company, make that your aim.

If you think you’re unable to be on the cover of Time magazine, make it your business to be there.

Make your vision of where you want to be a reality.

Nothing is impossible.
June 30, 2024

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