For as long as I can remember, when the winter months arrive, I wear a black leather jacket and a black knitted longshoreman’s hat.

The hat is basically a simple knit cap beanie; snug-fitting, brimless or minimally brimmed, made from wool or acrylic, originally worn by dock workers, fishermen, laborers, sailors, and stevedores.

I’m a creature of habit. When it comes to clothing, once I find something I like, it’s hard for me to change my mind. I didn’t grow up with the longshoreman’s hat. In suburban Canada, where I spent my childhood, the winter headgear of choice was the toque. Every year, classmates arrived with a fresh batch, probably bought from Eaton’s, Simpsons, or some other national retail chain. The hats were colorful, fuzzy, long, and often downright silly in a Bob and Doug Mackenzie way.

But during my cab driving days, I explored different clothing styles and imagery, and the longshoreman’s hat spoke to me. It was darker, cleaner, sharper, and far more aligned with the look I wanted to project.

There was a quiet toughness to the hat, a kind of minimalist confidence. I also believe it’s relatively hip and stylish. In some respects, I’m paying homage to a long line of people who have worn it: Jean Reno, who played Léon in Léon: The Professional (1994), wore one. So did The Edge, guitarist with U2. Wearing the black knitted longshoreman’s hat feels like joining that tradition.

But the appeal isn’t only symbolic. The hat is practical. It’s inexpensive enough that losing one doesn’t ruin your day. It folds down neatly into a jacket pocket without bulging or ruining the silhouette. And it looks intentional without trying too hard. It’s part of street culture without slipping into contemporary streetwear.

That said, not every black knit cap qualifies. There are rules. Buy me the wrong one, and it will sit untouched forever in the basket where we store our hats; get it right, and I’ll wear it for years. And it cannot have the insignia of a company, organization, or brand on it. I don’t want to be mistaken for a human billboard.

For clarity, here’s what makes a true black knitted longshoreman’s hat, at least to me:

1. Price: It shouldn’t be expensive. If I lose it, I should be able to replace it without thinking twice.
2. Material: A wool-polyester blend is ideal. All wool sometimes itches, smells when wet, and loses shape; all polyester causes my head to overheat and becomes uncomfortable to wear.
3. Knit: The knit must be tight, with no prominent ribbing. It also cannot be unnecessarily thick or thin, like a running cap.
4. Length: When folded once, the cuff should be about two inches and cover roughly half the ears. If the hat is too long, it’s probably a hipster stocking cap; too short, and it’s most likely a French fashion beanie, which seems a tad overdressed and a little kitsch.

For years, I could find a suitable version at places like the long-gone Hercules Army Surplus Store on Yonge Street in Toronto, or Canal Jeans on Broadway in New York City. Before Amazon, I had to hunt for them; now the search is easier, but my standards haven’t loosened.

Not only is the black knitted longshoreman’s hat both a look and a habit, but it’s become part of my identity. In this manner, it’s a small thing that somehow connects memory, utility, style, and a sense of belonging.