That’s Not A Fedora (And Stop Wearing It)

For upon |There’s a meme going around some circles that guys who wear fedoras are jerks. This tends to be accompanied by photos of guys who are not wearing fedoras. Instead, they have fallen prey to a devastatingly common trend in retro-fashion: the trilby.

I’ve seen shops that carry nothing but a hundred variations on this unfortunate hat. Guys retain vague memories of seeing old photos of Frank Sinatra wearing something similar, and assume that its powers will translate to them. They will blithely call it a fedora, unaware of the haberdasher’s blasphemy they are committing.

The structures of the two hats are similar, but the trilby has a sharper crown and, most importantly, a much narrower brim. This distinction may seem minor, but we are discussing aesthetics here, and a minor distinction makes all the difference in the world.

Trilbies, using less material and being more forgiving of poor fabric, are cheap to make and thus have become widely available. So on one level, a guy in a cheap trilby is saying “I wanted a hat so I just grabbed the first one I saw and considered that sufficient.” Worse, though, the simple fact is that trilbies look like crap on most men. They’re unflattering and unattractive.

The key to choosing a hat, for men, is simply this: a man’s hatbrim should be in proportion to his shoulders. Sinatra could pull off a trilby because, back in the day, he was a skinny little guy with a narrow, vertical-line aesthetic. Most men, however, have broader shoulders, and thus should wear a wider brim. A trilby on a big man looks like the reservoir tip on a condom.

If you’re a man who wants to wear a hat, I applaud you! They’re a great look, and there’s a hat out there for you. However, it is probably not on the hat cart at the mall. Unless you are a very slim little fellow, the trilby is probably not your look. Fear not, though: many good alternatives are available.

For the gent who wants to maintain a lean line, but wants a jaunty bit of class and a certain lighthearted style, the derby is an excellent choice. It’s fun, it can be formal or casual, and it’s not a goddamned trilby.

For those who really want a fedora, there’s always actually wearing a fedora. This is a great mid-sized brim for the gentleman with mid-sized shoulders, but a decent hat shop will have a variety of brim widths to best match your build.

Another great mid-size brim option is the porkpie, which you may recognize as the distinctive style of hat Walter White wore in Breaking Bad. This is a great casual hat with a certain flair to it.

For slightly broader shoulders and a great classic look, consider the homburg. You may remember Al Pacino rocking this hat in The Godfather, or Humphrey Bogart wearing one in Sabrina. It’s a hat with dignity and distinction.

Broad-shouldered men should also consider the slightly Western flair of the gambler style, a broad brim that provides a distinctive and noticeable silhouette. It’s a confident hat, one that stands out.

These are far from the only options, of course; there are many, many different ways you can go if you decide to wear a hat. All I ask is that if you decide to wear a hat, you wear a hat. Don’t go halfway, don’t nervously grab the first thing you find and hope you can pull it off. Find something that works on you and then work it.

And for god’s sake stop calling trilbies fedoras. They have different names for a reason.