Summer is nearly over. In addition to the days getting shorter, the air getting cooler and the trees changing color, sartorial concerns are foremost in some minds. In my case, my wardrobe is pretty constant—a good T-shirt and cargo pants get me through seasonal fashion shifts—with the exception of my hat.

Owing to climate change and my genetic predisposition for baldness (if I had my druthers, my locks would be long and wavy), I am compelled to wear hats to protect my pate from the harsh effects of the sun. It’s less fashion than practical. But since I have to be practical, I might as well be fashionable.

Each season demands a different hat: summer is straw. Early fall is straw, and late fall is felt. Winter is wool. Spring is straw again. I don’t vary the styles much. Fedoras and Panamas are my hats of choice, weather-permitting, otherwise a classic beanie will do. Stetson is my brand.

This Labor Day, I face a chapeau paradox. My current summer straw Panama, now in its fourth year, has lost its pristine charm, and cleaning is not feasible. I need to swap it out for a new model—but Stetson only produces the style for the European market.

I realize there are a lot of other things to worry about at this time, but hats get me out of my head, so to speak (and after all, this is Labor Day weekend and I don’t have much else to write about for the holiday).

The hats below are my late summer/early fall options. At top is my favorite Panama from Rome. Below that is a Fedora from a bespoke Parisian hatter on Rue Cassette. Under that is a Stetson Panama that I bought from J.J. Hat Center, the only hat shop I know of in Manhattan. Finally, a vintage brimmed cap worn by guides at the 1939 New York World’s Fair (I’ve been known to wear it outside when I’m feeling adventurous).

I am leaning, however, toward this new one. I’ll probably end up wearing my old faithful until it turns a sweaty shade of beige and the straw begins to fray. Have a happy Labor Day, and don’t forget to wear a hat (or sunscreen).

Steven Heller has written for Print since the 1980s. He is co-chair of SVA MFA Designer as Entrepreneur. The author, co-author and editor of over 200 books on design and popular culture, he is the recipient of the Smithsonian Institution National Design Award for "Design Mind," the AIGA Medal for Lifetime Achievement and other honors. He was a senior art director at the New York Times for 33 years and a writer of obituaries and book review columnist for the Times. His memoir, Growing Up Underground (Princeton Architectural Press) will be published in 2022.

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