Summarize:

One of the most identifiable elements of the cowboy style is a good leather boot with a hard wooden heel (Not actually wooden, is stacked leather). They can  take some getting used to, since the heels and sharp toes are designed for fitting a [stirrup] on horseback.  If you’re the kind of cowboy who doesn’t use his boots for much more than walking down the street, there are plenty of intricate and comfortable designs available. When a cowboy is working, he needs pants that are both comfortable and durable.  Most cowboys favor simple jeans, with straight legs or boot cuts. A hat is more than just an accessory for a cowboy – it performs essential functions.  A cowboy hat is traditionally worn to keep a cowboy’s head cool, to keep the sun off of his face, and to keep flying dirt out of his eyes. Fancy designer hats are readily available, but a real cowboy prefers an old, worn in hat, whose shape has been formed only over years of hard and constant use.  For a true cowboy hat, look for the Stetson or Bailey brands.  Choose a beaver fur felt hat for cold weather, and a straw hat for the warmer seasons.
Get a pair of boots. Slip on a pair of jeans. Don a hat.