The Basic Cowboy Look
The basic cowboy look includes the bare essentials – all the must-have items that immediately say “Cowboy” to anyone who passes you on the street.
Slip on a pair of jeans. 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, but designer labels and fitted styles are always an option in the 21st century.
Put on a hat. 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 nowadays, but a real cowboy prefers an old hat, 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 Baily brands. Choose a beaver fur felt hat for cold weather, and a straw hat for the warmer seasons.
Get a pair of boots. One of the most identifiable elements of the Cowboy style is a good leather boot with a hard wooden heel. Real cowboy boots aren’t overly concerned with design. They can also 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, however, there are plenty of intricate and comfortable designs available today.
Wear a Western style shirt. To advance your cowboy look, find a long-sleeved, button-down shirt, preferably with a plaid pattern. Thicker shirts, of course, can be worn in winter, and thinner shirts when it’s warm. Some cowboys do opt for a simple T-shirts, but rarely while working in the sun. Either way, the look should be rugged. Designer cowboy shirts might include some light embroidery, or a chest flap that snaps closed on one side.
Get a good belt and an even better buckle. Many cowboys prefer wide leather belts with large metal buckles, which are often made of silver or brass. These may have "western" themes, or the cowboy’s initials, or they may just advertise for a favorite tobacco or beer company.
Grow a mustache or a beard. Cowboys are like any other group of people - some wear facial hair, some don't. But working cowboys, who are often on the job from sun-up to sundown, don’t have much time for shaving.
The Extreme Cowboy Look
The Extreme Cowboy Look is well beyond the Basic Cowboy Look and the Advanced Cowboy Look. If you opt for this look, your life is probably already pretty cowboy. Out in the rest of the world, you’re sure to turn lots of heads.
Go outside. Cowboys work outdoors, not in corporate offices, so their skin is tan, leathery, and coarse from wind and sun, which they often see twelve hours a day, six or even seven days a week.
Skip the manicure. Cowboys don't spend a lot of time working on their fingernails, or trying to keep their hands baby-smooth and soft. Cowboy work makes for rough callouses and dirty nails. Cuts, bruises, and scars are regular sights on hands that spend their time working with fences, lassos, horseshoes, and other rough materials..
Get a duster. A duster is a long leather jacket, usually with large buttons, and sometimes with fringe in various spots. The duster is most appropriate during cold weather or while traveling. Like most things cowboy, the larger buttons are practical – they’re much easier to use with gloves on. A sturdy leather vest is a good substitute when the weather is warm.
Strap on the chaps. Chaps are perhaps the most extreme of all the cowboy wear. Chaps provide extra protection and while working on horseback and at the rodeo. It’s not advisable to wear chaps in many other settings. The same probably goes for spurs.
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