Fashion Five: Pat Riley, Menswear Dog, Handbook of Style, Japanese Boots

Every Sunday, I’ll share five ideas and content usually focused on fashion and menswear.

One of my fashion goals this quarter is to take more fit pics and document my style journey. Growing up, I was never comfortable in front of the camera. My dad and sister were always snapping family pictures on vacations and at parties, but I hated being in them. Deep down, it was because I wasn’t comfortable in my own skin. What’s been fulfilling about my style journey is that it’s helped me embrace who I am—and even overcome my fear of the camera.

Last Sunday, I was wearing my new Giant Chinos for the first time, paired with my favorite black leather boots and a tweed blazer. I was feeling my fit. I found a spot with a stoop to prop my phone on with aesthetic red-bricked apartments in the background. Perfect. There were a lot of people walking around. I pretended to be on my phone, looking up frequently, to make sure that I could capture the right moment so no one passed by. But there are too many damn people. I walk around the block looking for a different spot with less foot traffic. I found a decent spot with less people but the lighting and background wasn’t it. So I go back to my original spot.

This time, there weren’t as many people around, so I went for it. I placed my phone on a stoop with the front-facing camera angled toward me and hit record. As I was recording, I noticed a couple walking toward me. Making brief eye contact with them spiked my anxiety, and I quickly grabbed my phone to end the recording.

I don’t know why taking public fit pics feels so embarrassing—no one cares. In fact, as the couple passed by, the guy said, “Nice fit, man!”

Later, I asked a friend who takes public fit checks all the time how she makes it look so effortless. She told me that she still feels anxious every time, too.

It’s normal.

And honestly, I’m starting to enjoy the thrill.

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Recent style inspiration

Pat Riley, left, head coach of the Lakers and Jerry West, right, general manager of the Lakers. Riley and West helped build the 1980s Lakers dynasty, also known as Showtime, which brought 5 championships to the city.

Pat Riley and Magic Johnson

Known for his competitive intensity and meticulous attention to detail, Pat Riley is a 5x NBA champion as a head coach.

Pat Riley, the legendary NBA coach and current General Manager of the Miami Heat, was known for his sharp sense of style, often wearing Giorgio Armani suits on the sidelines. Armani even provided Riley with suits for free and made him an unofficial spokesperson for the brand. While NBA coaches are no longer required to wear suits since the pandemic, Riley’s vintage Armani fits remain iconic and a testament to his impeccable style.

Instagram account I’m looking at

@mensweardog. I first learned about Menswear Dog through my friend David’s recent podcast with Yena Kim, the creator behind the account. Over a decade ago, Yena started dressing her Shiba Inu, Bodhi, in menswear fits, and he quickly became a sensation, featured in GQ, The New York Times, and Time magazine. Sadly, Bodhi passed away last month, but his legacy continues to leave a lasting impression.

Book I’m reading

Cover for the Handbook of Men’s Style

Handbook of Men’s Style by Esquire. The Handbook of Men’s Style by Esquire is often recommended in the menswear community—and for good reason. It’s an excellent introduction for any man looking to elevate his style. The book is packed with practical advice, covering everything from wardrobe essentials to details like the ideal width of your lapels, and much more.

Video Series I enjoyed

Sole Searching by Stitchdown. The Japanese ironically do vintage Americana better than America and their boots industry is another example of this. They’ve taken heritage Western boot styles such as military, engineer, and work boots and not only replicated it, but elevated it in Japanese fashion.

Meme I laughed at

Me at every function. Shout to Andi for the share.

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Fit of the Week: Polo Boy

aron_ch

A post shared by @aron_ch

@Aron_ch is a digital illustrator specializing in Ivy style, and as I was scrolling through his archives, this particular fit caught my eye.

The outfit tells a cohesive story, blending classic preppy elements with a modern sensibility. The looser selvedge denim paired with New Balances brings a contemporary edge, while the timeless style up top anchors the look. This contrast creates an intriguing tension: the juxtaposition of polished, classic Ivy aesthetics with a casual, trendy vibe.

It’s one of my favorite outfit formulas: pairing a collared shirt or something more dressed-up with casual elements like “dad” sneakers or a baseball cap. The mix of refined and relaxed pieces adds visual interest and gives the outfit a unique, approachable charm.

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Have a wonderful Sunday!

See you again next week,

<3 James