Greenhorns choose cowboy hats solely on how they look on the retail rack or based on misleading impulse to buy they get after a quick glimpse in the try-on mirror. But savvier cowboy hat shoppers buy based on how well the Western headwear's crown complements the shape of their faces. The crown of a cowboy hat is the portion that rises most prominently from the top of the head; while the brim is the portion that extends furthest outward from the side of the head. Cowboy hats attract attention, and the key to drawing flattering glances is picking hats with crowns that balance out a person's facial characteristics.

Get the best possible approximation of your facial shape. By trial and error, you can free-hand a sketch of your face’s shape while looking into a mirror. A multi-panel mirror can make you more aware of prominent facial features (nose, ears, beard) that can throw the look of the chosen cowboy hat’s crown off balance and detract from your overall appearance. Friends or family members can help. Have them draw frontal and profile sketches of you.

If it’s determined that your facial shape is thin and elongated, select a cowboy hat with a crown of medium height. A crown that is either too tall or too squat will exaggerate the face’s narrowness. Hats with wider brims help balance out prominent ears and noses.

Pick a cowboy hat with a crown of medium height if your face is full or round. A crown that’s too squat should would make the face appear fuller, and a crown that’s too high would have a similar, distorting effect.

A person with a compact or small-chinned face should consider cowboy hats with lower crowns so that his/her headwear does not appear overwhelming. A crown tapered with a forward tilt at the top also helps deflect attention from a small chin.

Choose a hat with a higher crown and a brim that's at least medium if your face is oval. Hats with low or medium brims or trim brims won't flatter your face's dimensions and more likely would distort them.