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Could You be a Hat Guy?

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Scene: A young man in business slacks enters a hat shop. He makes a joke about the word “haberdashery,” on the door and chuckles something about Elmer Fudd. He walks over to the hat rack and plops a Panama hat on his head. It falls over his eyebrows.

Enter: Me. Your neighborhood haberdasher, or hat seller.

I ask the young man if he has a particular kind of hat in mind; he says no, he’s never thought of himself as a hat guy, he just stopped in for fun.

But there he is standing before me, his mere presence wordlessly expressing his intrigue: Could he be a hat person?

He grabs a trilby hat, raises an eyebrow, and makes a mock Sinatra face in the mirror. “Is it me?”

I cannot lie.

The trilby teeters atop his round face. He laughs at himself. “I never look good in hats,” he says.

“Don’t be silly,” I assure him, taking the trilby. “That’s like saying you don’t look good in shirts.” I hand him a felted fedora, “You just have to find the right one.”


Hats have moved from an expected element of every man’s wardrobe – circa 1930 – to a unique item that makes a statement about a man’s confidence and style. Deciding on one can feel like a big choice, committing to a definition of sorts. But it’s not all that grand. When it comes down to it, choosing the right hat is a utilitarian feat: it all comes down to face shape.
face shapes in sketches
Image adapted from The Fashion for Men
To determine your face shape, grab a tape measure. Go for a non-rigid one – the kind you find in a sewing kit rather than a toolbox – unless you want to have a really awkward encounter with your tape measure. (Please take photos for us if you do.)

Forehead: Measure the widest part of your forehead lengthwise – the points usually fall somewhere between the peak of your eyebrow and side hairline.

Cheekbones: Measure from the sharp bump just below the outer corner of your right eye to the same point below your left eye.

Jawline: Measure from the tip of your chin to the back of your jawbone (beneath the ear, where the jawbone angles upward). Multiply this number by two.

Face Length: Measure from the tip of your chin up to the center of your hairline.

Record these measurements and note the longest one.

Round Faces

Angular hats are best for round faces. The high crown and slanted brim of a fedora provides asymmetry for naturally symmetrical faces. The effect of the hat can be amped up by angling it forward or to the side. The best facial hair for round faces will give a more oval effect to the head, like a well-groomed circle beard. Whatever you do, don’t grow heavy sideburns if you have a round face … not even a fedora could help then.

The Fedora

1 FedoraFedoras are low, soft felt hats with a slightly curled brim and lengthwise crease through the crown. Over the years they’ve been popular with everyone from Humphrey Bogart to Michael Jackson.

The Flat Cap

2 Flat CapAlso known as a cabbie hat, golf hat, or ivy cap, the flat cap is rounded on top with a short, stiff brim. It’s most commonly made of wool or tweed. It traces back to 14th century England. See some familiar faces in flat caps.
Do I have a Round Face? Your cheekbones and face length have similar measurements. Your forehead and jawline (which also have a similar measurements) are shorter than your face length. You have a soft angle to your jaw.

Square Faces

A square face benefits from a bit of softening. We don’t all have to be boxers. The best hats for this face shape have rounded edges or a floppy fit. This look compliments a light but full beard, giving the face an overall more slender look.

The Bowler

3 BowlerAlso called a derby hat, the bowler hat features a rounded dome crown and a hard felt brim. It has its roots in the working class, but has since also become popular with British aristocracy.

The Homburg

4 HomburgThe Homburg is a felted “business formal” hat characterized by a dent that runs through the center of its crown. Rumor has it the design was inspired by a German hunting cap.
Do I have a Square Face? All of your measurements are fairly similar. And you have a sharp angle to your jaw.

Rectangular Faces

With a rectangular face, the trick is to accentuate the leanness of one’s face while at the same time giving it some roundness so it doesn’t appear unusually long. While a short brim tends to draw attention to long lines, a wider brim will draw one’s attention away from it. Along with having built-in sun protection from a wide brimmed hat, the long-faced among us arguably have the easiest job when it comes to shaving as well: the most flattering look for this face shape is the good old five o’clock shadow.

The Pork Pie Hat

5 Pork PieThe pork pie hat is characterized by a flat top, no crease, and a narrow, curled brim. It was most popular during the Great Depression. Its naming story is probably the most interesting in the hat chronicles, being named after, you guessed it, an actual pork pie.

The Cowboy Hat

6 CowboyThe cowboy hat is famous the world over. First made by John B. Stetson in 1865, it’s now a symbol of the west. People take their cowboy hats seriously, so be sure you know the proper way to wear one before setting off on the road.
Do I have a Rectangular Face? Face length is the longest measurement. All of the others are fairly similar.

Oval Faces

The oval face is probably the easiest for hat wearing. Almost any hat flatters an oval face. So why not go for some of the more interesting hat styles out there? While you’re at it, try a goatee with your trilby or a full beard with your top hat – it’ll all look good.

The Trilby

7 TrilbyThe trilby is probably the most confused with the fedora. But don’t be fooled: it has a much narrower brim. Historically, it has been popular among aristocrats, and made a comeback in the 2010s.

The Top Hat

8 Top HatThe top hat is a highly formal hat with a tall, cylinder-shaped crown. Counter to popular belief, President Lincoln’s famous headpiece was a stovepipe hat rather than the more demure top hat. While stovepipe hats have since faded into history, top hats are still going strong.

Do I have an Oval Face? Face length is larger than cheekbone width, and the forehead is larger than jawline (don’t forget, you have to multiply that one bytwo to get an accurate measurement). The angle of the jaw is rounded.

It’s not entirely fair that women have a whole slew of luxury items that quietly speak volumes about their taste and personality – Birkin bags anyone? Men’s choices are somewhat more limited. Or focused, one could say.

The proper hat can really elevate a man’s personal style from run of the mill to standout.

Have fun choosing!  Once you pick your hats, let us know: What’s your face shape? And what hats look best/worst on you?

About the author:
biopic_kaproKatie Kapro holds her MFA in nonfiction writing. She loves playing with style and giving her boyfriend really awkward haircuts. @kapro101

Katie la Kapro

Katie la Kapro

6 thoughts on “Could You be a Hat Guy?”

  1. I live in a small city, 60k people. How does one find a haberdasher? Other than the local western shops, “Lids” is the only hat store I’ve seen.

    1. Oof, that’s a good question. If there isn’t a hat store in town I propose swiping all of the hats off townspeople’s heads and starting your own. No, no that won’t work.
      At my shop we saw a lot of travelers come through – there’s something particularly nice about buying yourself a hat in a place you’re just visiting. It comes with a story. There’s a great little haberdashery in Harvard Square in Cambridge, MA if you’re ever in that area.
      Vintage shops are a good place to check too!

  2. Never cut your hair Brian!
    Long hair is great and hat hair bites. So I say the lesser of the two should be the one to conform. There are a few things that can help with hat hair. The biggest one is to make sure your hat has a bit of extra roominess to it. Think of trying on a hat like trying on pants – if they’re tight, they’re going to squish and constrain and leave marks on your waistline (or forehead, blarg). Flat caps can be especially good on this front because they have a sturdy band but also leave plenty of room up top for your hair to do its thing.
    Lighter materials too are especially good for controlling hat hair – look for something with a cotton lining.

  3. Brian Fiori (AKA T he Dean)

    Better to be a”hat guy” than “THAT guy”.
    Seriously though, I love hats. And I think I look good in them. Alas, I can’t wear them often. Not because of my face, but because of my hair. At some point, you will likely be sitting at a table, and etiquette says a gentleman removes his hat. My problem? Horrible hat head. I have long, very curly, hair. It cannot survive removing a hat without looking preposterous. I cannot comb or pick out, my hair, either.
    Yes, I could cut my hair, or get a new hair style. But I like my hair more than I like hats. Any suggestions, Katie?

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