Timely Hats for Seasonable Men - The GentleManual (2024)

The hat on this man’s head is a Tilley, and the man beneath it is Alex Tilley. For two decades his hatshave received a lot of attention, especially during the summer months.

Alex Tilleysold the brand, but the buzz over his bonnets persists and remains deserved.

Table of Contents

Rarely is a man either dazzling or imbecilic solely on account of his baseball cap. Baseball caps as a class are safe, but are stylish only when they do not diminish a good-look. Rarely do they make a look a goodone.

A Word on Lightweight Hats

The straw Trilby has made a remarkable comeback. Many men of a certain age (myself included) had mixed feelings when low-quality imported Trilbies began to grace the gondolas of H&M. It was great to see a classic back in vogue, and terrifying to know that – when it regained street-cred – it would hemorrhage cachet. That’s the price of popularity. Damn you, Instagram.

A certain kind of gent can wear a certain kind of Trilby to fine effect. As with the fedora and the Panama, the man daring enough to don a Trilby needs to have a strong sense of style. He also needs the confidence to wear the hat neglectfully. Let me repeat that word: neglectfully.

Hat Rule No.1

The man should wear the hat; the hat should never wear the man.

A fedora or Trilby needs to be the finishing-touch without it ever seeming as if is being worn solely because it isintended to be the finishing touch. The man who looks good in a brimmed hat knows it’s the right hat, and knows why it is; but he doesn’t wear it just because he knows it is the right hat. Yes, it’s a paradox — and that’s why few men get it right. Study Laozi and Sunzi, and you’ll grasp the logic of the lid — without grasping it.

A more seasoned gentleman can look dapper in a Panama; a younger man in the same hat risks presenting as affected, or comic. Younger men enjoy some discretionary latitude when it comes to Trilbies and pork-pies; older gents need to be careful not to look like pervs.

This, by the way, is the charm of the baseball cap: There are better and worse caps, and better and worse occasions on which to wear one, but rarely is a man either dazzling or imbecilic solely on account of it. Baseball caps as a class are safe, and they are safe because they are common — widely-distributed across genders, ages, trades, avocations, regions, ideologies, and socioeconomic strata.

Hat Rule No.2

Baseball caps are stylish only when they do not diminish a good-look. They never makean ensemble look good.

In recommending the Tilly, we could start by reaffirming the importance of not letting the summer sun bake your brains. The FDA recommends wearing hats, as does The Skin Cancer Foundation. Researchers have rated protective clothing (inclusive of hats) higher than they did sunscreen, and you probably do not need an MD to point out that hats do a fine job shielding one’s noggin from intense, direct sunlight. Fashion and style aside, there are times when you should be wearing a hat, irrespective of whether or not you wish to.The beauty of the Tilley is that it is an extraordinary field-tested sun shield. It is water-repellent and durable, and mold-resistant. It floats. It is also less theatrical than a fedora or a boater, more polished than a bucket hat, and less martial than a boonie hat — although we love our collection of boonies. On the beach, a cricket hat,Bermuda hat,or any old agglomeration of straw does nicely.

But then there’s that walk from the beach along the promenade or boardwalk, or that searing expanse of tarmac between your villa and favorite cafe. Made for the most inhospitable environs of terra incognita, it is in civilization (and on its fringes) that a Tilley shines. This is a rugged, hard-wearing hat that never looks cheap and always looks particular. It derives its visual earnestness from its well-balanced “function-first” proportions, not from “tacticool.” If there’s something about a Tilley that says “been there, done that,” it’s because the man wearing a Tilley probably has. And that’s a look that can’t be faked.

Mad About These Hatters

There is a ton of Tilley testimonia out there — stuff like this from Field & Stream.

The Filson packer hat, and “FDR’s summer hat” from Duluth Trading, caught our eye.

If you’re going to buy your first boonie, start withthis classy number from bestmadeco.com.

An aficionado? You need one of these, too. We sure do.

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