Struggle To Find The Perfect Hat To Wear ( Updated 2017 )

You think Pharrell Williams in his very high Vivienne Westwood hat is so cool and maybe, you will have that cool if you top off a look like him. However, at the time you put that hat on, nightmare is coming as it makes you look like an old bald man.

Or you can’t count how many hours you have spent to find a perfect hat but, alas, up to now, you still don’t. Here at Coolmenstyle, I don’t prefer to see my buddies up and down the country struggling to pick his right hat. Thus, in this article, I will enlighten you with my style guide. Read on!

The Most Basics You Should Know about Hats

1. Terminology

When it comes to choosing a perfect hat, you should know some basic terminologies. Don’t fret, I used to be a guy who didn’t have any idea about them, too. Just tried a hat, if it looked good on me, I would pick it.

But, sooner and sooner, when I did some research about hat’s terminologies, I realize that they help a lot as I can see the difference and know particular features to look for a good one.

Here, I swear, it’s very easy to remember:

Styles of hat

Look at these two pictures, not mention their color, do you think they are different hat styles? And can you distinguish them? Having knowledge about almost styles of hat helps you not only figure them out, but also find out which one is suitable.

I’ll give an example on those two hats above, they are ivy and newsboy cap. With a newsboy cap, a man with top-heavy face will be perfect in it. However, he won’t be suitable in an ivy cap because the design of this hat will make his face look “heavier”.

Up to now, there are quite a lot styles of hat and cap. Here I’ll name some of them:

  • Pork pie hat
  • Fedora hats
  • Derby Bowler hats
  • Gambler hats
  • Outback hats
  • Top hats
  • Bucket hats
  • Driver and Ivy caps
  • Newsboy caps
  • Baseball Caps
  • Greek fisherman caps
  • Pub and duckbill caps

If you are not sure about your knowledge on hats and their styles, I think you should consult this guide:

How to distinguish the most common hats and caps styles for men

Face Shape

In the previous part, I have just given you an example of how suitable of different cap styles on a top-heavy face. And yeah, this one is about the influence of face shapes on choosing a perfect hat/cap.

If you either don’t know about which kind of face shape you have, you should. Sometimes, with the same hat but your friend looks handsome in it, but you don’t. Or as I said from the beginning, maybe Pharrell Williams is suitable with Vivienne Westwood hats but you aren’t. It’s because your face shape is different from him.

Commonly, there are 7 face shapes overall:

Oval Face

If you have this face shape, I must say that the world of hats is opening up to you because you can pretty much fit any style hat. However, still remember that your face shape is slightly rounded off, you should avoid those hats/caps that make your face look wider or the roundness of your face look more clearly.

In particular, don’t pick any hats adding height, roundness or width to your face. A safe choice is medium crowns as they will make your face shape in proportion. Try fedora hat and Gambler hats. Avoid snapback and baseball caps


  • Medium width brim
  • Medium, squared crown


  • Round crown

Long, Thin Face

Like oval face, long, thin face can match almost styles of hat. Yet, there are also some things you should avoid whilst choosing a hat/cap. Contrast to an oval face, a long, thin face should stay away from anything that make it look even longer. Choose a hat style that shortens and widens your face so that it will give an illusion of proportional ratio.


  • Wider brim and band
  • Shorter rounded crown


  • Squared off crowns

Consider bucket hats, baseball caps and snapbacks, they will be your healer. These hat styles are also hot trends for this summer while you can mix and match with many cool fashion looks. Give them a try!

Square Face

This is a common face shape which has box like shape because fairly even all the way around. Those guys who own square face will have masculine look. However, because of their rigidness, you should look for a hat that makes your face shape appear more curvature, less boxy.


  • Rounder crown
  • Medium height
  • Wide brim combines with the edges rolled to create round shape whilst narrow your face


  • Boxy crown


  • Homburg style
  • Baseball cap
  • Fedora hat with the round crown design and the brim rolled

You may concern:

Best fedora hats for men

Which is the best baseball cap?

Top-Heavy Face

This might be the first time you hear this kind of face shape. A top-heavy face has a wider head at the top, but will be narrower to the jaw, which means that you need something top heavy to balance your face ratio.


  • Medium brim width
  • Medium to short crown


  • High crowns


To avoid highlight your top-heavy face, give up those hats with high crowns, which means you may say goodbye to Vivienne Westwood hat. Instead, you opt for a classic straw boater or a fedora hat. They are also versatile hats which you can mix with your casual outfit.

Round face

In this case, my advice is to carry out the asymmetry rule. It means that you should choose a hat whose design is opposite to your face shape. Confuse? Here is an example. If you have a round face, all you need to look for is a hat style with high squared crown because it will be a slimming treatment to your face shape.


  • High crown with straight brim


  • Wide round crown and brim
  • Tall rounded crown


  • Ivy caps
  • Top hats
  • Greek fisherman caps

Oblong face

The highlight features of oblong face are round chin and longer-than-wide face shape, which means it is fairly straight lines from jaw to temple. Thus, to avoid accentuate them, you ought to pick those hats with flared brim and high crown to make your overall look a bit more proportion.


  • High squared crown or short rounded crown
  • Flared brim


  • Flat or narrow brim


  • Newsboys cap
  • Fedoras hat with large brim
  • Cloche
  • Sun hat


Heart-shaped face

For those men who have heart-shaped face, you should choose a hat that helps you to even the width of your forehead. To cause attention of the others as well as create a new look, you can slant the hat to one side. This will also help you make your face look narrower.

In reality, any kind of hats will be well-matched on you, but the ones with large brim. Thus, remember this exception.


  • Medium brim


  • Large brim


  • Cloche
  • Boater
  • Homburg
  • Fedora with a medium sized brim
  • Beanie
  • Beret


Choosing a suitable hat for your face shape is not enough, you need to consider a high-quality one. That’s why you should choose the material cleverly.

From my experience, almost hats have the same material. They are usually made from condensed mat with very tough and sturdy fibers to keep its shape. For example, top haps, fedora hats, or baseball caps. They all need a tough material to keep their square or round crown and large to medium brim.

The most common fibers are wool, tough fabric, leather, straws and tweed which not only offers toughness and durability but also keeps warmth and breathability.

To know whether a hat is a high-quality product or not, just hold it on your hands and feel their softness. Then, bend it up and down. If it’s a good one, the hat will be bent easily, but when you release it, it will return to its original shape rapidly.

Choosing the hat’s material also depends on which season you want to wear it. For example, if you choose a hat for summer or going to the beach, consider straws and tweed. On the opposite, pick a leather or wool hat to wear on the winter.

There are also hats made from animal furs/hairs such as beavers’ hairs. These are usually very expensive so that if you want to try a luxury feel, try them out.


Along with the kind of material and the brand you choose, the price will be up and down. Therefore, while choosing a hat, you should consider their price and your budget.

Commonly, the price of a hat is from dozens to hundreds of dollars. Some luxury hats from high-end brand may be up to thousands.


When it comes to the hat’s size, you should know that we are talking about the inside circumference of the hat’s trim. Like clothes, hats have many different sizes, which means you should know your head size to pick the right one.

Choosing a hat without caring about the size is a bad idea because if it’s too loose, the hat will fall in front of your eyes. On the contrary, a too tight hat will make you feel like headache for long time wearing or uncomfortable.

If you choose to buy a hat online, the very first thing is to measure your head. All you need is a flexible measuring tape, you can take measurements quickly the circumference of your head on your own. Have a look at the video below, it will guide you the right way to do it:

Last but not least, you should remember that each hat brand has different sizing charts to convert from your head’s circumference to the hat sizes. Thus, if you wear a particular size of a brand and want to change to another brand, you should have a look at their sizing chart to make sure which one is the best for you.


In summary, there is four main things when it comes to choosing a perfect hat:

  • Does it suit your face?
  • Does it fit your head?
  • Is it high quality?
  • Your budget for it

A hat might be not the main items on your outfit, but it is an accessory to not only protect you from sunlight, but also make you look better. Thus, don’t ignore when you choose one, don’t throw your money through window. Invest on it and wish you have the best hat from my style guide.

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