StyleJonathan Cavaliere

Are You Ready for the Hat Renaissance?

StyleJonathan Cavaliere

Are You Ready for the Hat Renaissance?

There is one item that never ceases to perplex fashion-oriented people of all stripes, from the beginner to the expert. It’s an area of interest for many, yet understood by few. I’m speaking of course about the cherry on top of our outfits–hats.

Legend has it that John F. Kennedy’s alleged choice to not wear a hat to his inauguration killed the popularity of the accessory. While there is plenty of reason to dispute that theory (including the fact that JFK did in fact wear a hat that day), the observation that hats largely went from a wardrobe staple to a relic of bygone times is an accurate one–or at least it has been until recently.

Many believe that hats are currently making a comeback. Thanks in part to hipsters, in part to those who love to rediscover forgotten gems of the past, and in part to the enduring functionality and stylishness of certain hat types, we may very well be on the brink of a hat renaissance.

Hats are (in some ways) like cats. You either hate ‘em or you love em’. But even if you love them, there’s a catch. That catch is that some of us are so inexperienced and unfamiliar with hats that we may not know what to do with them (much like with cats). I’m sorry to be the bearer of bad news, but many of us may even run the risk of trying to look like a high class gentleman while actually looking like an amateurish joker. I wouldn’t want to see any of us accidentally go down that road to embarrassment.

Never fear, though, because the rules of hat life are actually quite easy to master and the gains are worth the non-existent pains.

When it comes to donning a chapeau, there are four main things to know: the style, the size, the setting, and the outfit.

There are countless different types of hat styles out there spanning virtually every time and place in human history, so one short article won’t do them justice. Luckily, our current comeback trend focusses on two biggies –namely, the fedora and the trilby.


Now, if some of you are currently asking “what is a trilby?”, you’re not alone–although in truth, most people should actually be asking themselves “what is a fedora?”

It turns out that the more common style worn today is actually the trilby, which, psyche, is commonly mistaken for a fedora. Somehow, society has forgotten one of the names and one of the styles, and has mismatched the one of each that it remembers! So let’s set the record straight.

A fedora is a wide-brimmed, flexible felt hat with a pinched crown, and can be adjusted and physically manipulated into shape using your bare hands. You will likely recognize this style if you’ve ever watched old gangster movies, and its most famous wearer was probably Hollywood legend, Humphrey Bogart. This was the most popular style of the first half of the 20th century, and is probably why the style’s name is so familiar to us. Nevertheless, by technical hat standards, only hats that meet this specific set of criteria can be called a fedora, and using the term so broadly as to apply to other styles does nothing but drive hat enthusiasts mad.

So what, then, is the kind of hat that we have all been mislabeling? You know, the kind that has a crown and brim but is usually smaller, can be found in a wider variety of styles, and holds itself naturally in shape at all times? This hat is known as a trilby. It is a thinner and far more casual style, and can serve a broader set of purposes today than a fedora. The most famous wearer of this style is likely music superstar Frank Sinatra, who wore it long before it became the go to style for hat wearers that it is today.

With regards to finding the right size for one’s hat, there is one golden rule: the size of one’s hat should be proportional to the width of one’s shoulders. This is one of the biggest rookie mistakes people make when they decide to just plop a hat on their head one day without any of the prerequisite knowledge. If you’re a slimmer than average gentleman, you will probably want to go for a thinner trilby style. If you are broad shouldered, you should be going for the wider fedora style. And while we’re on the subject of golden rules, hat enthusiasts also have one with regards to where to wear a hat. Put simply, it’s that a hat should always be removed when you are indoors. This is another frequent violation by many first time hat wearers who simply don’t know any better. Regardless of what style you’re wearing, knowing to take it off when you enter a room or building is an immediate way of separating yourself from the amateurs.


Finally, there is the question of how a hat fits in with the rest of your outfit. While this may be more open ended depending on the standards of modern society versus previous decades, the key has traditionally been that hats are meant as an accessory, not a centerpiece. If the Sinatra or Bogart look is what you’re going for, it would be very difficult to achieve that by just adding a hat to a T-shirt and basketball shorts combo. A hat’s role from a fashion perspective is to punctuate an outfit, but that only works if there is an outfit there to be punctuated. This is probably the most overlooked rule of hat etiquette nowadays, but remains a legitimate point of contention nevertheless. If you really want a hat to look right, I strongly recommend accompanying a fedora with a suit or with at least a business casual outfit for a trilby.

So, gentlemen, the secrets are now yours to make use of. You now have the knowledge you need to separate yourself from the amateurs and to identify yourself as a member of the elite few who know how to put elevated head gear to good use. In other words, you’re ready for the hat renaissance.  Bring it on!