How Should a Hat Fit? [2021 Fit Guide]

Hats are not the fashionable accessory that they once were. You won’t see many sporting the bowler in the west nor the Turkish cap in the east.

However, there are still those that believe in the classic sartorial aesthetic enough to care about hats. Hat sizing almost seems like a lost art.

In a world where everything seems like it’s ready made and nothing is fitted, hat fitting is also very tricky. However, if you’re one of those few souls that ask “how should a hat fit”; this is the guide for you.

How should a hat fit?

The definitive guide to how a hat should fit – measuring your hat size

Step 1: Get a Measuring Tape

Before you begin the exercise of measuring your hat size you’ll need a few things. The first job is a flexible measuring tape.

This isn’t the one that you can draw out of a little box. This is the one that tailors usually hang over their necks and is made of soft vinyl. This doesn’t stretch, and bends very easily.

If you don’t have yourself one of these measuring tapes then you can make do with a piece of string. You can even use a ribbon if you want. Just make sure that whatever you use doesn’t stretch or elongate in any way. Get a marker or a fountain pen to mark specific places on the string or ribbon.

Also, decide on one unit of measurement. Don’t use feet, or meters, of course. Use centimeters or inches.

Stick to one type of measurement unit so you can make do with what you have. Converting in between those units can often lead to imprecise measurements and thus imprecise selections.

Choosing the perfect hat size for your head

Measuring Your Hat Size

It’s both an art and a science to do this. Using a tape measure or a length of string will work fine.

However, there are two ways you can do this.

First Method: Straight Measurement

Place the string or the ribbon or the tape measure 1/8” above the year. It should measure across the mid-forehead and circle your entire head. Make sure that you don’t circle your ears. The tape should also be held firm against the sides of your head. No portion should be loose.

Also make sure that you’re not gripping the head too tight. Remember, you’re sizing for comfort as well as for fitting. You don’t want a hat that fits your head but squeezes the blood out of your skull. Also, the sizing measures are just guidelines which you can build on. If you like to wear your hat a certain way, like tilted, then you should size for that. Just make sure that the measurement you choose shouldn’t be uncomfortable in any way.

Second method: Comparison method

A valid method to determine your hat size is comparison as well. It should warrant telling you that it’s no replacement for straight measurement. However, if you’re in a hurry and want something to keep your head covered and warm, go for it.

This method is best used for a trip or an event which you need to dress for at short notice. I don’t recommend this for those that need to dress for a ball or a ceremony they know of beforehand.

Other methods:

You need to simply try on a random hat the next time that you visit a hat shop. Sizes are universal, but they can vary a little depending on the manufacturers. This is why sizing hats is technically better than comparing.

You can refer to sizing charts like this one to convert a vague size like ‘medium’ to a measurement. You should also note here that unlike other accessories or apparel, sizes can vary from one manufacturer to the next. There is no guarantee that every size that you will find there will be a perfect fit.

This is why you should pick out a haberdasher or a hat shop that you trust. Just like a tailor or a barber, a haberdasher should be one that you can trust with anything. They should know your taste and your measurements without any need for reminding.

If you still have any inhibitions then you can use this hat sizing chart to help you make the right choice.

Miscellaneous tips for sizing a hat properly

There are various small tips that have emerged over the years from hat connoisseurs to fit any hat perfect. Take your pick.

  • Use hat tape to adjust how a hat fits on your head. This is also called a hat size reducer. These are usually foam strips that have adhesive on one size. It sticks to the inside of the sweatband. This creates a very secure fit. If you choose a hat that turns out to be a little looser than you though, this is the best corrector.
  • When choosing a hat you should know the body’s proportions. Don’t just look at your face. Judge how the hat looks in comparison to your shoulders and your waist. Judge how it goes with your ears, eyes, stomach, etc.
  • Remember that the hat literally will top off your look. Make it so it’s a welcome addition.

Measuring your head for a hat

How to choose from different hat types


The classic Fedora has been used in movies almost as much as the bowler. It was used for gangster movies, surrealist French cinema, the new age movement, etc.

You may also remember it from a certain adventurer named Indiana Jones.

It’s a great hat to have. So when you pick one out, make sure it’s minimalist and that it matches your attire. You may try to wear it tilted to the side over one ear if you’d like also.

What kinds of hats can you wear?

Baseball Cap

Baseball caps are pretty fashionable among US citizens, with it being a national pastime and all that.

Make sure it fits the head but doesn’t squeeze. This will literally go with any casual attire that you have on, as long as you’re not going for a work or formal look.

Just make sure to get one that’s minimalist if you’re not supporting any specific team.

Flat Cap

If you want to look like Tommy Shelby from Peaky Blinders, this is the hat for you.

However, you should sport a classic look with it. Don’t wear a hoodie and flip flops with it. Wear it with a three-piece suit or a polo shirt.

Also, get one that isn’t too close fitting. They’re designed to be worn forward, not backward. So give it room to be shown off.


Beanies should accommodate your head type and hair. One that messes up your hair or squeezes your head is not your friend.

Also make sure that the beanie covers your hair if it’s short and covers just enough if you have long hair. I’m a fan of cashmere, but that may be a bit much for your budget or your style.

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