Hats are more than fashion. They have been prevalent in every culture since the dawn of time. Whether it was an Egyptian Pharaoh, a Canadian Mountie or a Christian parson, a hat has always signified a person’s status and class and instantly creates a vibrant first impression.
Nowadays, men are experimenting more and more with their headware. Older men are donning newsboy caps and male models are wearing beanies in July. This experimentation can be exciting and fun; however, many other people find themselves unsure and silly exploring new hats. And the excuses are everywhere: “My head’s too big!”… My head’s too small!”…“I am not stylish enough to wear a hat!”…Whatever your excuse, there is a hat that is right for you.
In truth, a hat is the ultimate reflection of one’s personality. Finding the right one might mean doing some self-exploration. The more you know yourself and how you want to be perceived, they easier it will be to find the right hat.
The work will pay off. Let us get started by examining some of the more popular styles throughout the ages. Try them all on if you must, but remember some basics.
Fedora
One of the most classic kinds of hats, a fedora was often the first choice for icons like Frank Sinatra and Humphrey Bogart. It is categorized by a tall crown that tapers forward, and a brim that occasionally tilts down. It is worn on the front of the head, and the brim should fall right above your eye line.
Who can wear this type of hat?: Classic, older and more sophisticated gentlemen work best in fedoras. The size of the hat requires a sizeable personality. (Think Indiana Jones.) With the right look, a fedora can work, but it can quickly skew a bit tacky if not worn correctly.
Who should beware?: Always keep a fedora classy, as cheap and ill-fitting ones might make you seem too big for your britches. The shape of the hat means that a fedora must fit correctly, and the large crown usually makes fedoras trickier for the bald men out there. Anyone with larger foreheads should also be wary.
Note: A trilby (see below) is often confused by some people as a fedora. However, they are very different hats.
Trilby
A trilby is a popular hat among younger guys these days. Often confused with a fedora, a trilby has a much smaller brim and a taller crown. It is often worn towards the back of your head. The Blues Brothers wore trilbies.
Who can wear this type of hat?: Younger, hipper types usually wear a trilby best.
Who should beware?: The popularity of this particular hat has made them widely available at any mall or department store. However, the cheaply made versions (some using more flashy textiles) have garnered the trilby a frat boy reputation. Wear a trilby with the right style and it will work, but keep it subtle.
Porkpie
A porkpie hat has a crown which is the same height all the way around, and a stiff brim. Unlike a fedora, it does not feature a tilted brim and it does not taper in front. Most famously, Walter White, from the television series Breaking Bad, donned an iconic porkpie.
Who can wear this type of hat?: Men of all ages, who are confident, trendy, a bit dapper but not incredibly sophisticated or formal. The porkpie is usually best for a more city-type, though a country man could look great in one too.
Who should beware?: Porkpies can get a bit too hipster-y. To avoid this, be sure to never pair a porkpie with suspenders, a long beard or a PBR. A man with a pointier shaped head might also struggle with a porkpie.
Homburg
Homburgs are a classic style of hat. Though less prevalent nowadays than fedoras or porkpies, they are usually easily worn and add a touch of sophistication. Usually taller than a porkpie but lacking the taper of a fedora, they are characterized by a single dent in the center. Al Pacino donned a homburg on The Godfather.
Who can wear this type of hat?: Strong, sophisticated gentlemen. More mature and more formal gentleman. Whereas a porkpie can be dressed down, a homburg is a bit more formal.
Who should beware?: Men who tend to dress casually will find a homburg harder to wear. Men with smaller heads might also find the hat difficult to not get lost in.
Newsboy, or Flatcap
The typical style of an early twentieth century newsboy, the flatcap is a cotton (or wool), pliable hat with a stiffer brim. The simple design allows for a great deal of malleability, and many men can find a flatcap that works for them. Nowadays, they come in various textiles and styles.
Who can wear this type of hat?: Almost anyone can find a flatcap that works for them. A more popular style for gentlemen with shorter (or no hair, it is a casual hat for more casual occasions. Personable, easy-going guys wear them well.
Who should beware?: Younger faces often look comically younger in a newsboy hat. If you have a baby face, maybe consider another hat.
Beanie knit hat
A beanie is the typical snowy weather hat. A knit cap that is worn tight and close to the head, it gives the wearer a cue ball look (unless of course it has an iconic pom-pom)
Who can wear this type of hat?: Cold People. While the beanie has become a bit more popular with younger gentlemen, the hat is most appropriate (and encouraged) for it’s practical use on colder days. As a non-practical fashion choice, it is usually best on very young gentlemen.
Who should beware?: People who live in warm climates do not really have much use of a beanie.
Slouch knit hat
A slouch knit hat is the beanie’s more hipster-y brother. Larger, and not worn tight to the head, it has a breezy and youthful vibe to it.
Who can wear this type of hat?: Super laid back men, guy into winter sports and musicians can get away with this hat. It definitely has a bit of California attitude about it.
Who should beware?: Anyone over the age of the 40 should really rethink this style.
Baseball cap
Probably the most prevalent hat in any man’s wardrobe, a baseball cap is also the most casual. Widely accepted and seen around the world, a baseball cap will always dress down your outfit.
Who can wear this type of hat?: The most casual, sports- loving types probably already own one. Like any hat, baseball hats should also be very personal and reflect the owner and his love for a team (or color).
Who should beware?: Anyone going to any formal occasion should NEVER wear a baseball cap. Also, be sure that the brim of the baseball hat you choose looks nice on you. Even with baseball caps, it is important to try on a few.
Cadet or Military hat
Similar to a baseball cap, but with a squarer, more structured crown, a cadet cap is a great alternative for a casual cap. The textile does not have to be camou or green, as military is simply the cut and structure of that hat.
Who can wear this type of hat?: Anyone looking to upgrade his baseball cap can usually find a decent cadet hat.
Who should beware?: More formal types, or anyone unrelaxed. The cadet hat is a stronger, but still casual hat.
Cowboy hat
Another classic. The cowboy hat is large, brimmed and categorized by the strong dent and taper to the front
Who can wear this type of hat?: Rugged, authentic cowboys and men like them.
Who should beware?: It is very easy for a cowboy hat to look like a costume. If you don’t have a cowboy soul, the hat can easily start wearing you.
Straw hat
A classic option, a straw hat was popular in the late nineteenth and early twentieth century. Made of straw (of course), it is stiff and rarely has a dent on top. Wearing one is definitely a nod to another time.
Who can wear this type of hat?: People who can strongly embrace the old world charm. Old souls who still have a bit of quirk are ideal wearers.
Who should beware?: Most people should beware as a straw hat (like the cowboy) can look like a costume. If the pizzazz of a straw hat feels like it fits into your personality, wear one.
Bowler Hats/Derby
A popular hat for many years, a bowler (or derby) is known for its rounded, dome-shaped top and prominent brim. For many years, bowlers were seen as a status symbol in the U.K. Today, they are much less prevalent.
Who can wear this type of hat?: Hipsters, or people unafraid to wear a hat that is an obvious throwback to an old school classic.
Who should beware?: Most people will find that nowadays a bowler is a trickier look to pull off.
Top hats
Known to be the ultimate sign of high class society, a top hat, or topper, is tall with a broad brim and a flat crown. Abraham Lincoln wore a “stovepipe hat”, a style of top hat he helped popularize in the mid-nineteenth century. Toppers are still worn by British royalty and other society folks, though they have all but disappeared otherwise.
Who can wear this type of hat?: Magicians, Mr. Peanut and Lincoln impersonators.
Who should beware? Top hats (even more than bowlers and cowboy hats) are instantly perceived as costumes. Avoid the perception and consider a homburg, fedora or porkpie.
With that, it is time to get to work. Explore different sides of yourself and you will certainly find that perfect hat – no matter your head size, or personal style. The search is half the fun. My hat’s off to you! See you at the haberdashery!
