A well-fitting cowboy hat should feel secure without being tight. It shouldn’t slide around when you move your head, but it also shouldn’t leave marks on your forehead. The right fit strikes a balance—snug enough to stay put, comfortable enough to wear all day.

Factors that can affect how a hat fits

• Head Shape – Some people have round heads, others more oval. Most cowboy hats are oval-shaped by default.
• Hat Style – Different crown shapes or brim widths can affect how a hat sits.
• Material – Felt hats may conform more with wear, while straw or palm-leaf hats tend to hold their shape.

What to look for in a proper fit

• The hat sits about ½" to 1" above your eyebrows and ears.
• There’s a light grip around your head, especially just above the temples.
• You should be able to tilt your head forward or backward without the hat falling off.
• It shouldn’t feel like it’s squeezing or pinching at any point

1. Use a flexible measuring tape – Cloth or tailor’s tape works best. If you don’t have one, use a string and then measure it against a ruler.
2. Wrap the tape around your head – Measure where the hat will sit: about ½" above your eyebrows and just above your ears. Make sure the tape is level all the way around, not tilted up or down in the back.
3. Keep the tape snug, but not tight – It should feel like a comfortable hat fit—not pinching or loose. Don’t pull too hard or leave extra slack.
4. Take note of the measurement – Record it in inches and centimeters, if possible. Most hat sizing charts use inches or fitted sizes like 7 ¼, 7 ⅜, etc.
5. Double-check the fit – Try measuring twice to be sure. Small differences can affect your final size, especially if you're between two.

Already measured your head and checked the size chart? Here are a few more things that can help you get the best possible fit. These tips may be especially useful if you're between sizes or buying your first cowboy hat.

• Try on hats late in the day – Your head can swell slightly throughout the day, especially in warm weather. Trying on hats in the afternoon gives you a more accurate sense of how they’ll fit during real-world wear.
• Match the fit to how you’ll wear it – Some folks wear their hat flat and low; others tilt it back or perch it higher on the crown. Measure and choose your size based on how you naturally wear your hat.
• Account for seasonal changes – Felt hats worn in winter may feel different than straw hats worn in summe. A slightly looser fit might be more comfortable in cold weather with added layers.
• Check brand sizing before you buy – Not all cowboy hat brands use identical sizing. A size 7 in one brand may feel tighter or looser in another. If you're loyal to a brand, use their official chart for the most accurate match.
• When in doubt, size up and use inserts – It's easier to make a hat fit tighter than to stretch one that's too small. If you're between sizes, go with the larger size and use foam tape or a hat liner if needed.