How To Measure Your Head For a hat to fit properly, it is very important to measure your head size correctly before ordering. This is actually very simple. Using a tape measure, the type a seamstress uses is best because you can easily wrap it around your head (a piece of string will also work). Place the tape measure (or string) around your head slightly above the eyebrows and ears, approximately the width of a finger. If your measurement is tight, your hat may also be a tighter fit. A Loose measurement will result in a looser fitting hat. Take note of the measurement and repeat two or three more times to ensure a correct measurement. ( measure the string against a tape measure ) and find the measurement on the chart closest to yours. If you have not ordered a hat for a while, be sure to re-measure, as different hair styles, weight gain or loss, aging and other factors can give you a different hat size today than in the past.