How To Measure Your Head For A Fitted Hat. A good way to test a hat’s fit is to simply use your finger — if you can fit one finger between your head and the cap then you know you have the right size. Adjust the tape measure so it sits in middle.
Also make sure that you’re not gripping the head too tight. Although it is a matter of personal choice, a good spot to measure is the widest part of your head, as that’s where a hat often fits the best.
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Basically you need to measure your head exactly where the hat will sit. Be sure to hold the beginning part of the measuring tape and wrap in around your head slowly and deliberately.