I like to wear a trilby. Do I look like a prat?
Actually, if you must wear a hat (I am nervous of hats generally, unless they are serving solely to keep your ears warm), a trilby is the least prattish way to go.
A trilby is a – wait, before we get to that, what is a prat? I love this insult, as it is so specific and so frequently clothes-oriented. Dictionaries will tell you a prat is a fool, plain and simple, and that it comes from slang for buttocks. But I find in use the word has class overtones: It seems to mean not just a fool but a pompous one, a conservative one, a guy so conventional he looks like an advertisement for pedantry. Brits in ascots and tweed, carrying silver flasks, are often called prats. So I'm not surprised at your hat-related fear. Hats with brims, particularly wide brims, can seem like the terminally boring person's most flailing attempt at appearing interesting.
A trilby, however, is restrained. It is a soft felt or tweed hat with a narrow brim and an indented crown. It is the most commonly worn type of men's dress hat in North America. If it is smooth felt it is dressier; tweed versions are only for walking in the country. Its back brim is always worn snapped upward.
Now there is great and impassioned debate about what distinguishes a trilby from a fedora. Some will say that a fedora is a larger hat with a wider brim. I have always maintained that a fedora was any hat with a brim that could be snapped up or down – in other words that fedora was the larger category and trilby was a subset of it. (In other words, all trilbies are fedoras but not all fedoras are trilbies.) Current usage, though, seems to have settled on the former distinction: In Canada at least, a fedora is known as the more dramatic Indiana Jones-style hat with a wide brim. In other words, it is goofier. Wear a big fedora and risk looking like a guy who also wants the biggest boat and the biggest signet ring and the biggest pinot noir.
Note that neither one is a porkpie, which has a flat crown.
A trilby is neat and gentlemanly. Just keep the hatband plain – no feathers. And remember to take it off as soon as you step indoors.
Interestingly, both trilby and fedora are words that came from the theatre: a play called Trilby (1895) and a play called Fedora (1882). Trilby, the play, was based on the novel of the same name that also gave the world the word Svengali, after a charismatic character in it. You see what I mean about drama? Hats are drama, drama, drama. You want to go easy on that.
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