Winter Style Notes: 'City Boys'

The enduring influence of Popeye magazine's "City Boy", and why it matters.

One morning last week, I put on a pair of dark green wide-legged cords, a loose blue-and-white striped cotton shirt, an oversized red wool knit jumper and blue alpaca wool socks. The next day, I wore the same loose-fitting shirt, but with a long A-line chambray shirt, an oversized navy knit vest, and black merino wool knee socks.

Winter is nearly upon us once more, and this year, I’m revisiting the formula that worked pretty well for me last year—big on big on big.

Recently, I was flipping through my old magazine stash, and I realised there’s a term for this: “City Boy” style, as coined by Popeye magazine.

A page from an editorial styled by Akio Hasegawa. I can’t read Japanese, but according to Google Translate, the key sentence is the line at the bottom of the page: “Ordinary clothes, nothing special.” Taken from Akio Hasegawa’s Instagram account.

Specifically, I’m thinking of the neo-trad iteration of “City Boy”, as put forward by stylist Akio Hasegawa, who among many things, was Popeye’s fashion director between 2012 to 2018 (he still does amazing work for the magazine), and does styling work for brands like Engineered Garments and Nanamica.

He also runs his own website AH.H (full of inspiration and great styling ideas), and I’m always falling in love with his work before I realise he is behind it (like this super cool editorial for Nepenthes).

A selection of Akio Hasegawa's styling work via his Instagram account.

This loose, layered “City Boy” style appeals to me because it’s functional—hardwearing fabrics, sensible, sturdy shoes—and in sync with my casual lifestyle needs and tastes. But it’s also one of those styles that you can take and interpret your way—maybe your tastes run gorpcore, maybe it runs trad, maybe it runs a little folksy-eclectic. There’s room to incorporate personality.

Two takes on the City Boy style in one editorial; the look on the left is more sporty, and outdoors influenced, while the look on the right is more draped and elegant. Styling by Akio Hasegawa.

And unlike “Ametora” (a Japanese portmanteau that means “American Traditional”, often iterated as Japanese Ivy¹), it’s more relaxed, less costume-y, and crucially, friendly to all genders (even though you rarely see women represented Popeye). Maybe the baggy-on-baggy look takes some getting used to, but for me, it it feels liberating.

It’s also not a look that comes down to owning “the right piece”. Yes, a Needles HD trouser, a hard-to-find Nautica Japan navy wool peacoat, or a pair of Visvim boots are highly covetable, but City Boy style as defined by Hasegawa is about celebrating the beauty in the ordinary.

I’ve always liked the look but I never really got into it until I moved to Melbourne and had to dress for winter—beyond a loose shirt or big tee with baggy shorts, all the other artfully layered looks didn’t really lend itself to the tropics. (That said, Hasegawa does make a big blue shirt, nylon army shorts and runner flip flops feel super stylish.) Here in Melbourne, I found myself drawn to winter wear with a lot of sturdy volume, and suddenly, I was channelling the City Boy life.

My budding attempts at channelling City Boy style.

Popeye magazine itself has a pretty interesting history—it was launched in 1976 to sell a fantasy version of the American West Coast lifestyle to Japanese youths. Yes, exactly like how “Take Ivy” sold a fantasy version of Ivy League prep to Japanese youths a decade earlier, to huge success.

The vibe of Popeye in 1976 was “Amekaji”, or “American Casual”, and you can think of it as Ametora’s cool, laidback younger brother—instead of the collegiate, sporty trad Ivy look (Oxford button-downs, sport coats, loafers, khaki pants), it was more casual and Americana influenced (Levi’s 501s, Red Wing boots, baseball or letterman jackets, M-65s).

Not that there was anything casual about how Popeye took the aesthetic. Its debut issue dedicated seven pages to sneakers, together with instructions on how to jog, surf, skateboard, and hang-glide, and a “27-page feature on the campus of a distant school called the University of California, Los Angeles”².

In a 2016 interview, Yoshihisa Kinameri³, the founding editor of Popeye, talked about why he’d sent four staffers to Southern California in early 1976 to capture the West Coast lifestyle.

“It’s hard to capture the feeling now, but then, it was just all so different. We had seen running in the Olympics, but seeing jogging in real life was completely strange…The hang gliding, the skateboarding, the variety of sneakers. It was all totally new. In Japan at the time, students had maybe two kinds of sneakers, and they were cheap and not stylish at all.”

“In Los Angeles, people looked happy and cheerful,” he added. “It was magical; it was like heaven.”

Ametora and Amekaji hold a special place in my heart, because it introduced me to a very specific reaction towards American (and western) cultural dominance that I had never seen before. I grew up in Singapore, a former British colony, during a time when we looked to American and European powers as model for social and economic progress—you could say we aspired to “democratic values” as preached by western powers (we were very naive).

Being ethnic Chinese I grew up speaking both English and Mandarin⁴, but there was never any doubt which was the language of progress. And even though I watched plenty of Chinese-language cinema and TV shows, read Chinese books, and listened to Chinese and Cantonese pop, all of this at the time was heavily influenced by American culture. In short, whether we liked it or not, the West led the way.

The exception to this cultural (and economic) dominance in the late 1980s and 1990s was of course, Japan. J-pop and other aspects of Japanese contemporary culture occupied the rarified position now held by K-pop; in style and fashion, everyone looked at what Japanese stars wore. We admired the daring cool of Harujuku girls, and beheld the likes of Yohji Yamamoto and Rei Kawakubo in hushed reverence.

Japan, was no doubt, also heavily influenced by the West, but it adopted Americana as a language of rebellion, and it earnestly remade it according to its own sensibilities⁵. And in doing so, it made it better. Long before I understood what “representation” meant, Japan was the only Asian superpower I could think of that owned its culture proudly and held its own. It taught me that cultural dominance could be countered by interpreting it on our own terms.

Looking through at my old copies of Popeye, I realise it’s not only the aesthetic that resonates with me, it’s also the significance of the magazine’s history⁶ and what it has come to mean over time.

Long live the City Boy⁷.

Via Akio Hasegawa’s Instagram.

1. W David Marx’s “Ametora: How Japan saved American Style” is a lovely deep dive into this topic. This interview with him captures some of the essence of the book.

2. “How Japan invented Los Angeles and reinvented American style”, Los Angeles Review of Books.

3. Yoshihisa Kinameri died on July 13, 2023. RIP.

4. Singapore is a multi-ethnic country and the government recognises four official languages (Malay, English, Mandarin and Tamil). In school, English is the language of instruction, and everyone studies English as the first language. Our respective mother languages are studied as second languages.

5. Read this little ode to Japanese magazine culture in the Financial Times.

6. See all the Popeye covers over the years here.

7. There is nothing quite like Reddit when you want to dig into a subculture. Threads on City Boys here and here.