The Material

A cowboy hat is a beloved possession: It fans fires, it blocks the rain, it gives shade—and it lends authenticity at any honky-tonk or greased-pig contest. But it’s also an extension of one’s personality, so commissioning one takes serious thought (and serious dough: from $300 to $1,500). The first decision? Felt or straw. Felt hats are made from varying gradations of beaver and rabbit furs, 100 percent beaver being the best quality; high-caliber straw hats are woven from Mexican palm leaves. The pros and cons: Felt is water-repellent, but it traps heat; straw allows breezes to circulate, but it lets UV rays through. And while a straw hat may be cheaper, it shares the shelf life of a gallon of milk, whereas a felt hat may easily outlast your dairy cow.

The Style

“A well-made hat tells a story about the individual wearing it,” says Chuck Wilkerson, the co-owner of Mike’s Custom Hatters, in Longview, the official outfitter for Missouri’s Roy Rogers–Dale Evans Museum. Most shops offer a wide variety of brims (widths range from four to five inches) and crown styles, such as the flat-topped Gambler and the pear-shaped Tycoon creases or the subtle Montana pinch. At Mike’s, ranch hands order the Cattleman, a classic wide-brimmed model with a prominent center crease and two deep crown tucks. Choose from just about any color, but if you plan on actually roping little dogies, pass on pure white—ivory resists dirty work much better.

The Fit

Take heed lest you measure improperly and fall victim to a common malady: hat headache. “Wrap the tape around your head about a half inch above the brow bone and the ear,” says Kelly Owens, the co-owner of Limpia Creek Custom Hats, in Fort Davis, a company recently given the sole honor of creating replicas of hats once worn by John Wayne. “Measure the circumference of your head to the nearest eighth of an inch, divide by pi [3.14], and that’s your hat size.” Also be prepared to answer a few fitting questions. Do hats leave red marks on your forehead? Your head is probably oval-shaped. Do they leave you tender above the ears? Your head is likely a uniform sphere.

The Flair

No cowboy headgear is complete without a hatband, that fashionable necessity used to cover up the hatter’s stitchwork on the sweatband. The traditional choice? A simple felt strip matching the hat color, fastened with a small buckle. Braided leather lends a rustic look, while a gold-and-diamond chain, say, sends a message about your recent interest in the Barnett Shale. The options, in short, are limitless: West Texans are said to favor turquoise-studded bands, South Texans go for silver conchos, and cowgirls statewide have been known to request tassels, good-luck trinkets, or feathers. (Note: Elaborate requests equal more money.) You might even channel your inner Duke and order an engraved sterling silver hatband. Talk about a real feather in your cap.