Fashion Five: Bob Dylan’ Jeans, Engineer Boots, Alexander McQueen, How to Layer, and Toronto in 1958
Every Sunday, I’ll share five ideas and content usually focused on fashion and menswear.
Hi all!
I arrived back home in Toronto from NYC yesterday.
One message I often share is that our clothes tell stories. As I was going through my old closet, I found myself reflecting on the memories tied to different pieces. Today, I want to share the story behind my Dragon Ball shirt.
Back in high school, I was in a Hot Topic at my local mall, and I saw this bright orange shirt with Japanese kanji. It was the iconic Dragon Ball shirt that Goku wore in most of the series. I had to have it.
In my first semester studying engineering at Waterloo, my worst subject was CHEM102: Chemistry for Engineers. I struggled through the entire semester, barely staying afloat. When finals week arrived, I knew that the Chemistry exam would be the most challenging. I studied like my life depended on it. I needed all the help I could get.
On the day of the exam, I was figuring out what to wear. Then the idea came of wearing my Dragon Ball shirt. Wearing that shirt made me feel like Goku. Just as Goku transformed into a Super Saiyan after being pushed to his breaking point by Frieza, I was ready to face my antagonist: this final exam. CHEM102 had been my nemesis all semester. It was time to take it down.
I walked over to DWE and took a seat in the front row. I had my calculator ready. I had my writing utensils ready. And I had my Dragon Ball shirt on. I couldn’t fail now. I gave that exam everything I had.
When the results came out later that week, I discovered I’d barely passed with a 55 (just over the 50 needed to pass). I had survived. I’d won.
From then on, any time a daunting exam loomed, I’d whip out the Dragon Ball shirt. It became my battle armor in college, my personal symbol of resilience and determination.
As many of us return home for the holidays, I’d love to hear about the stories and memories that come to mind as you go through your childhood closet!
Anyways, let’s jump into this week’s fashion five!
I) Bob Dylan’s Jeans
In preparation for the Bob Dylan biopic, Levi’s Vintage Clothing released a replica of Dylan’s custom jeans for an eye watering price of $495. His then-girlfriend, Suze Rotolo, had cut a U-shape from the hem and filled it with contrasting denim fabric. This modification created a wider leg opening, allowing boots to drape nicely.
II) Engineer Boots
One thing I often write about in this newsletter is how menswear is deeply rooted in function. Ever since watching a series on Japanese boot makers, I’ve noticed many of them specialize in crafting Engineer Boots. Originally created in the early 1930s for train engineers and workers, these boots were designed to provide protection from sparks and debris. They feature a tall shaft for added coverage and signature leather straps at the top and around the ankle for support and adjustability.
III) On Alexander McQueen
Runway shows are more than just a showcase of clothing—they're performance art, offering a glimpse into the artist's perspective, worldview, and emotions. This reel brilliantly analyzes the tortured genius of Alexander McQueen, focusing on the creative direction behind one of his magnum opus works, Voss.
IV) Why Great Outfits Understand Layering
Layering is a fundamental styling technique. Drew Joiner breaks down 7 laws of layering to help you level up any outfit. Here’s a brief summary:
What is seen can be appreciated
Alternating patterns and textures create the most intrigue when separated by another layer
Balance your colors
Thin to thick > thick to thin
Balance your proportions
Create windows into your layers
Nail the details
V) Toronto in 1958
I was born and raised in Toronto, and over the past two decades, the city has changed so much. Looking at photos of Toronto from 1958, it feels completely unrecognizable. The skyline is entirely different—there’s no CN Tower (it wasn’t completed until 1976)—and even the highways, including the QEW, have drastically changed.
Fit of the Week - Japanese Workwear
A new style inspiration of mine is Minoru Matsuura, the founder of Brass Tokyo and Clinch Boots. His style is a masterclass in how the Japanese reinterpret American workwear, often surpassing the original in creativity and execution. Much of what he wears is rooted in heritage American clothing, but his approach gives it a distinctly modern and personal twist.
Using layering principles from Drew Joiner’s video I shared above, let’s break down his outfit:
Layering with Intent (Rule 1 & Rule 2):
Minoru applies the principle of "what can be seen can be appreciated" by buttoning only the top button of his chambray shirt. This creates a visual "window" that showcases the henley shirt underneath, adding depth and texture to the outfit. Personally, I might have buttoned the middle buttons while leaving the top and bottom open, but the way he does it—buttoned just at the top—feels effortless and cool.
Proportional Balance (Rule 5):
He balances the oversized chambray shirt with equally oversized painter’s pants, creating harmony in the outfit’s proportions. This relaxed silhouette emphasizes comfort while staying true to the workwear aesthetic.
Attention to Detail (Rule 7):
Minoru’s attention to detail is evident in every element of his outfit. The distressed painter’s pants, likely worn during real workshop use, add authenticity and a sense of life lived. His handmade boots, crafted by his own hands, elevate the look with their refined craftsmanship. These boots—most likely Clinch boots—tie the outfit together and highlight his dual role as a business owner and artisan.
Thanks again for subscribing! I’d love to hear some quick feedback on what you enjoyed and what you would like to see more of.
Have a wonderful Sunday and Merry Christmas to those who celebrate!
See you again next week,
<3 James