Originally worn by Englishmen solely in the country, the tapered TRILBY, with its unfinished edge to the brim, has a distinctively informal style.

Throughout the first half of the last century, a hat on a man’s head was as common as a pin through his shirt collar. Indeed, up until the late 50’s, were a man to appear in public without a hat he would have been considered under dressed. Back in the anti-establishment 60’s and the fashion free-for-all that defined the 80’s and 90’s, some considered a man wearing any form of headwear as, well, overdressed.

Curiously, hats are once again popular, especially among young American actors who are championing the cause. Yet if hats have straddled the fashion spectrum over the decades, from propriety to superfluousness, Hollywood has certainly done its part to continually keep them in vogue. Who could forget Sidney Greenstreet and his Panama, so personal a signature to his sinister style that for a time any similar straw hat was called a Greenstreet. Rex Harrison never looked dandier than when donning his soft tweed Irish fisherman’s cap in “My Fair Lady.” Al Pacino, as Don Michael Corleone in “The Godfather,” was a model of formidable, if not imposing, elegance when donning a black pin striped suit and an oxford gray fur felt Homburg.Today American hat manufacturers are enjoying a Renaissance of sorts, with healthy sales of snap brim Fedoras in the style worn by Harrison Ford as Indiana Jones, who looked every bit the dashing adventurer in his beat-up version.

It is fitting somehow that certain hats and the actors who wore and continue to wear them on the screen have become so etched in our collective memory. The most classic gentleman’s hat, the Fedora, takes its name from a character in an 1881 tragedy by French playwright Victorien Sardou. And the Trilby, a trimmer, more compact version of the Fedora, was named after the central character in a book and stage play by English author George du Maurier.

Few in the know would argue that the Fedora deserves credit as the first low-crowned, soft hat for men. But popular as it was throughout the 20’s as an alternative to the stiffer Homburg for finishing off dressy town suits, when clothing became a bit less formal and tweeds found their way into town, so too did the Trilby.

Originally worn by Englishmen solely in the country, the tapered Trilby, with its often unfinished edge to the brim, had the distinctively informal style that was appealing, particularly to men in America. And when Edward VIII, Prince of Wales, endorsed the snap brim softer hat by appearing in one in public, the Trilby’s popularity soared on both sides of the Atlantic.

Perhaps the greatest virtue of the Trilby, or “sloucher” as it is sometime called, is its pliability, which allows the wearer to work the shape of the crease or angle of the brim in a manner that suits his personal style. Just as individual is the hat’s tilt; unlike the stiff Homburg or bowler, a snap-brim style offers a man his choice of angle, although it should always be worn slanting to the left (according to history, men once wore their ladies’ plumes in the left side of their hats and tilted them to prevent the feather from being slashed by an opponent’s sword. This is also the reason the bow on a hat’s puggeree is always on the left side of every hat today).

The best Trilbys are made of genuine fur felt, usually rabbit, which is one of the strongest fabrics since the short fibers bond well when they are wet and steam is applied. Apart from being lightweight, the felt is highly water-resistant and resilient enough to be easily pressed back into shape should it become overly damp. Hand-sewn leather linings, otherwise known as sweat bands, are another trademark of quality Trilbys, much preferred to the glued-in variety often seen in inferior versions.

Actor Johnny Depp is a Trilby aficionado

Experts seem to agree that a Trilby is an excellent choice for a first hat since it looks good on virtually anyone—perfect for those who want to play it safe with his headwear or may think they don’t look good in a hat. Yet despite its compact, relatively conservative style, certain rules apply, at least according to clothing designer Alan Flusser. In his book, Clothes and the Man: The Principles of Fine Men’s Dress, Flusser contends that not all hats look appropriate on every individual. “The height of the crown and the width of the brim ought to be in correct proportion to the size and shape of a man’s head and face,” Flusser writes. “A man with a narrow face should wear a hat with a narrower brim; otherwise the heavy shadowing of the hat will make him appear even thinner. Conversely, a man with a rounder, wider face, or with facial hair, ought to wear a hat with a wider brim, lest he risk looking like Oliver Hardy.”

True or not, Flusser’s contention appears valid enough. But regardless of whether you subscribe to the principles he has put forth, one thing is for certain: Oliver Hardy is one Hollywood legend whose sartorial style no man should envy.