The trilby has become the cheesy default hat for too many men, and it’s a mistake.
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.
Top Photo—Luke Hayfield Photography/Flickr
All other images from Wikimedia Commons
Late to this game, but here’s my contribution: In the U.K. they call(ed) them all Trilbies. Both “fedora” and “trilby” originated at almost the same time and first appeared in theatrical plays. Nomenclature is arbitrary by nature and some flexibility is required. What the author is calling a trilby is often called a stingy brim fedora my hatters, milliners, and the folks at the fedora lounge website. Both wide and narrow brim hats have their places and people with all sorts of body and face shapes can look good in both. My personal feelings are that wider brimmed fedoras look… Read more »
THANK YOU for this! Wear whatever you want, but at least know WHAT you’re wearing.
I think youre completely full of shit. I think Trilby’s look good on a lot of guys….me included.
More than Sinatra, I think of the Blues Brothers
I disagree with you on one point. The trillby and fedora are the same hat! They started calling fedoras with a narrow brim trillby to make a distinction between the two styles. But that doesnt mean its an entirely different hat altogether. Get your facts straight.
I’ve read disagreement about whether the famous Frank Sinatra hat is a trilby or a fedora. Frank Sinatra has worn many fedoras and has been photographed in them. Frank Sinatra has also worn many trilbies and has been photographed in them. Frank Sinatra has also been photographed wearing homburgs, high hats, and military hats.
Whether or not a trilby is a type of fedora depends upon your definition of fedora — and there is more than one. One authority says that it must have a wide brim, and another says that it *usually* has a wide brim. The same with respect to material. Some say that a fedora must be made out of felt, otherwise it is not a fedora no matter how it looks otherwise. Some define a fedora as having a center crease. Does that mean that if it is steamed and the crease is reshaped into teardrop it is no longer… Read more »
Some people say that trilbies are cheesy and the guys who wear them are jerks. Some people say that the guys who wear *fedoras* are jerks.
I believe that people with unkempt hair, sloppy clothes, and stupid looks on their faces look like jerks no matter what kind of hat they are wearing.
But if they have sloppy clothes it wouldn’t be regardless of what they are wearing since you specifically called out what they are wearing
Whether or not a person would look “better” wearing a classical fedora than a trilby is not only determined by his facial shape, shoulder width, and wardrobe, but by the style of the era. In the 1940s and 1950s, practically all men wore fedoras and looked good in them. Trilbies would look odd on them. When it was stylish to wear wide lapels and wide ties, *narrow” ones would look old fashioned. When *narrow* lapels and ties were popular, *wide* ones looked out of style and old fashioned. The same can be said for the length and bagginess of men’s… Read more »
With respect to the remark that wearing a trilby makes people look like jerks, I think that the people with unkempt hair, sloppy clothes, and stupid expressions on their faces who are pictured with trilbies would look like even bigger jerks if they were wearing classical fedoras. Some people look better in trilbies, some look better in fedoras.
What is the hat that Frank Sinatra is wearing on the cover of the That’s Life record album from 1966?
I enjoyed the article but didn’t think it was necessary to call the trilby ‘unfortunate’. I am a hat wearer and most that I own are trilbys. I think they really suit me but then again I am slim and of smaller build so perhaps that is why. Fedoras are good also but I tend to find them less comfortable to wear. One hat not mentioned in your article is the boater which is another style which suits me and is very comfortable to wear.
Thing is, most of these only look good when you’re wearing a suit. Or at least a button-down shirt and tie, which used to be common. Anything less than that, you’re better off with a ballcap.
Only if you can pull off a ball cap. My head is shaped in such a way that a ball cap would make me look incredibly redneck, and that is a style i definitly wish to avoid haha
I thought that a Trilby was fedora as well, but know i have a fedora and realize the difference. I not hate the trilby, but i love the fedora, Now that i could find a store selling it in Buenos aIres. Also i have a Funyi the classic BS.AS hat. Well i have many hats models, that i love to wear. I’m going to wear the fedora as well the trilby.
So many guys on here upset at this article because the author is basically saying they look like a dick when wearing a trilby – the CORRECT name of the hat. But, being guys, they refuse to believe they could ever not look good. Newflash: you look like a dick.
News Flash: Your opinion, touted as gospel truth, is nothing short of fallacious. Your OPINION doesn’t mean shit in the wide world, after all.
“There’s a meme going around some circles that guys who wear fedoras are jerks.”
I think that this post, if anything, confirms that.
I have broad shoulders, I love my nice trilby that I bought years ago from a used discount vintage clothing shop, and given all of the compliments that I get when I’m wearing it, I think that this article is pure hogwash.
Those people commenting on your hat are just trying to be nice..”if you have nothing nice to say…” kind of situation.
They really think its weird and/or your a dick.But rather than laugh or make a nasty comment, they said “i love your hat”. Trilbies fall under the same category of weird…er… dickish things? as socks with sandles, bronies over the age of 12, and Guido blowout haircuts.
I got tired of reading the ignorance about half way down and only saw ONE comment that actually had a lick of sense to it, and that was from Derek, the 50 year young fella [dated January 12, 2014 at 4:28 am]. So if there were older posts I missed, apparently the more recent posters did too, so I will reiterate and elaborate on Derek’s statement. A trilby IS a fedora. The ignorant posters here, would by the same logic state that a square is not a rectangle (fyi, it is). A trilby is a fedora with a shorter, or… Read more »
Well said, Justin.
Hats off to you, sir!
Your ipse dixit “logic” is fallacious. A tribly is not a fedora, nor is a pentagon a hexagram. There is no commutative axiom where members of a set are perforce identical, except in n-dimensional topology. A three piece suit is not a two piece suit is not a blazer is not a sport jacket. A trilby is not a fedora. They are two different things.
Noah Brand YOU ARE MY Hero!!!! I grew up in a time when MEN knew how and DID wear hats!!! My Dad could “Rock” a Fedora from Dobbs like nobody’s business. He was also a Snazzy dresser and hand painted ties were all part of putting a mean wardrobe together!! As YOU can tell this was the 1940’s and 50’s!! I loved your article because you KNOW what you’re talking about. The Trilbie doesn’t cut it with me and I’m female. I agree with you — a man should wear a HAT if he’s going to WEAR a hat. Thank… Read more »
A perfect article about hats I have read after long time people many time mix up all these hats but you have defined it in a very edifying manner.
I wear Fedoras, Homburgs, Gamblers, and in the summer wear my Cuenca Panama hat. My Fedoras are brand name hats like Dunlap, Cavanagh and Stetson. My Panama Fedora hat I bought in Cuenca, Ecuador. Most of my hats range in price from $280 – $2700. My youngest son came home one day wearing a trilby hat that he wore and just threw around, and that’s what those Wal-Mart type hats are for. Modern Trilbys are hats that very young men wear, because you can buy them for like $7.00 at Wal-Mart. When my youngest son turned 18, I bought him… Read more »
It’s so nice to know that there is a man in the world who knows how to dress. Any well dressed men I know are dressed by their wives. My husband refused to allow this and usually looked like hell. I love homburgs and when I was growing up, all men wore hats, and suits. They replaced felt hats with straw in the summer, Grandpa had a real panama hat. I also notice lately that if a man wears a tie he doesn’t wear a jacket, and if he wears a jacket, no tie. I don’t get it. I think… Read more »
I agree. I’m a 21yo college student studying archaeology and as a joke one day I started dressing like Indy (for field work it’s the classic look and then in class it’s a suit and tie) and after awhile the look just stuck. I own a Penman Last Crusade Indy hat which cost me around 560 dollars (beaver felt) and nobody and I mean nobody has ever thought of the “trilby” look ever. I get Indiana Jones almost everywhere I go but nobody ever confuses my fedora with a trilby. I think this whole “trilby is a fedora and you’re… Read more »
Since when mentioning the prices of one’s hats became a means of showing class? Well, it does show the opposite: no class. Clearly, someone desperately wants to be seen as upper class by talking about the dollars they spent: often again and again in one post. Bourgeois are always entertaining.
Trilbies are trilbies… and Fedoras are fedoras. They are two different hats that can give a good sense of style depending on the one who wears it. Fedoras are nice but should be worn and paired with a collared shirt. While trilbies are more flexible and looks good, not only with a collared shirt but even when paired with a non-collared top. It’s the person who gives character to what he wear depending on the attitude on how he carry his clothes. So, wear what fits you, what makes you comfortable, and what makes you happy. In our evolving world,… Read more »
The width of the brim on a man’s at has more to do with the shape and width of this face than the width of his shoulders. I have very broad shoulders but look ridiculous in broad-brimmed hats, because with my prominent cheekbones, narrow lower jaw a prominent chin, I’d look like a skeleton in a broad-brimmed hat.
Other than that, I wouldn’t take advice from a pretentious fashionista. I choose style over fashion any day.
My favorite hat that gets me an unlimited amount of compliments is my ‘Bromley’
So, is the hat worn by Thomas Jane’s character in “The Expanse” a short-brimmed Fedora or a Trilby? By this article and the few close-ups I’ve seen, I’m guessing Fedora?