Men's Vintage Western Styles: How to Get That Classic Cowboy Look

Maybe you're thinking this Halloween you'd like to revisit your childhood, maybe you just landed a gig as a drummer in a country band, or maybe you just want to go country retro. The classic country western look is, well, a classic. Almost every man can pull it off with a minimum of fuss and a relatively tight budget if they're willing to build up the pieces for their wardrobe over the course of a year. This hub is designed to show you, the novice country western wear aficionado, how to build up a low-maintenance, high-fashion, retro country western wardrobe with ease.

The Cowboy Hat: Nothing beats a well-shaped leather cowboy hat. Between the hat, (if you decide to go leather,) and the boots, here is where the majority of your budget for country western gear will go.

If money is an issue, or if you won't be wearing your country western gear often enough to justify the expense of a genuine leather cowboy hat the next best thing is felt. Felt hats are less heavy than leather cowboy hats and usually much cheaper. Sure, it doesn't look as smashing as the full-on leather cowboy hat, but the difference in price is usually too huge to be ignored for those on a serious budget. After all, you can always buy the more expensive leather hat down the road.

Another option is the "straw" hat. Personally, I think these should only be worn during the summer or at hot outdoor shows. They're flimsy and tend to get crushed easily, so don't count on the straw hat to be around for too long, or be your only cowboy hat. Relatively inexpensive, the straw hat is a good back-up hat for those shows or outings where you're worried about inclement weather.

Both the leather and felt hat will need to be fitted, sometimes the fitter will also "shape" the hat.  I've seen this done to felt hats and it's a really cool process.  I wouldn't recommend buying a hat online, unless you're really sure about the sizes, styles and colors you want.

The jean jacket is one of the most versatile pieces of clothing in existence second only to the basic white tee. Like their jeans, cowboys tend to wear their jean jackets on the narrow side. The darker blue denim is more tradition, as is the dark brass buttons, but you can get a little creative here, if you'd like. Chances are, any jean jacket you might have laying about in your closet will probably do just fine, unless "Metallica" is embossed on the back. Make sure that the jacket fits well and is warm enough for the weather you'll be wearing it in... one of the fantastic options are wool-lined jean jackets... it adds to the bulk, but you'll appreciate it on those chillier nights!  

The vintage cowboy dress shirt isn't necessarily about what cowboys actually would wear, back in the day, but more about looking fly.  One of my favorite classic cowboy looks it the long-sleeved plaid shirt.  Colors range within reasonable to "good grief, that's awful, why would you put those colors together?," and also come in a lighter short-sleeved variety.  I own one of each, (the short-sleeved and long-sleeved,) both well-loved and cared for.  Both were given to me in the eighties from my Aunt Val. 

Another option is the super-fly dressiest of dressy vintage cowboy shirt, shown below.  These shirts are not for the timid!  While I know a few guys who can pull them off, it's a rough sell for the average guy and a serious investment. 

They're a bit cost prohibitive, too, a good dress cowboy shirt will run you around sixty to eighty bucks, though I've seen some as low as thirty. Another fun option I've seen at one of the local store around me that specialize in vintage wear is the classic plaid shirt with a twist: at the shoulders they've sewn old-school kid's bedsheets. (We're pretty sure they're super-clean, right, guys?) The place is called Jive Monkey and it's right off the Belmont El. I wish I had some pictures of the shirts, they're really cool, but if you're ever in the Belmont 'n Clark area, you'll just have to check the place out for yourself: 3222 N Clark St. .... If you go to Google and input Jive Monkey Chicago, IL they'll show you a picture of the store that I couldn't upload to here.  Then come right back!  (Looks like a fun place to shop, right?)

The country western belt buckle is not a necessity of an authentic cowboy look, but if you can pull off the skinny bootleg jeans and tucked in country western shirt, an awesome belt buckle will really make the outfit! I think the best place to shop for a good belt buckle is in the store with the help of a sales associate. I'm not a tucker, (and I'm a woman, to boot,) so I don't have much experience with this. I know what I've seen at shows, though, and it looks great if you can pull it off. When you go out to get your hat, (it'll need to be fitted,) you'll possibly be buying your boots there, too. That is probably the perfect time to get your belt buckle, too. The associate is invaluable in helping you to pick out something that will look good with the over all outfit, bring pictures of your shirt / jeans, if possible so they can get a feel for the overall look your going for. Although you'll want to seriously consider their advice make sure you're not talked into something that doesn't match your personality or style, after all you'll be making the final decision and you don't want to be stuck with a (possibly,) expensive piece of accessory that is just going to end up junking up the back of your closet. A neutral color will probably work best, depending on the coloring of your boots and hat, so make sure the sales associate takes those items into consideration, as well. The belt buckle is probably the last item you'll want to buy on your list, just to make sure everything blends and looks as well put together as it can. Furthermore, make sure your belt buckle has a little room to grow. (No offense guys, but I've been told that the only thing worse than an expensive belt that is too small to wear anymore is trying to fit into an expensive belt that is almost too small to wear anymore.) Have yourself fitted for the belt, hat and boots. You'll thank me later when you're walking around all fly and comfortable.

Boot jeans are typical cowboy fare as far as jeans go for a reason: you don't have to practically rip your boots up trying to get your pants over them.  (We're not tucking our jeans into the cowboy boots, right guys?)  I like a more traditional dark wash, not necessarily black, but the nice deep rinsed indigo.  Again, I think it's better to be as neutral as possibly with the colors, if you pick black jeans, typically the shirt, boots, belt buckle and hat will all be in black.  Try wearing that during the summer, it's not pleasant.  With something like the indigo rinse you're a little more free to futz around with the colors.

There is nothing like a good pair of cowboy boots. After a few months or so of regular wear cowboy boots will form themselves to your foot and become like a second skin. In order to get a good fit, to be sure of quality and color it's best to buy your boots at a store that specializes in cowboy boots or western wear. Utilize the sales staff, if a store doesn't give you unique attention, move on to another store or come back when they're less busy. Make it clear that you're not walking out of the store with anything less than the perfect pair of cowboy boots for you, if you don't find them today, you'll be back again. Good clerks will appreciate a serious customer who can rely on their expertise. Like the jeans, hat and belt, be color conscious when choosing a pair of boots. Black boots might look flashy, but they are severely limiting when it comes to color co-ordination. Try different styles of boots on, your boots should be about a size larger than what you normally wear, definitely a size larger if you get pointed toe boots. Stay away from pointed toe boots, though. It's up to you, but I've never met someone who said they were comfortable, personally I don't find them attractive on a man. I've always thought of the pointed toe boot to be more of a girl thing, which isn't true, but that's just me.  Ask the clerk if there is a good cobbler, (do they still call them cobblers?,) they can recommend in the neighborhood when you buy your boots.  Having the boots resoled and the heels replaced is a lot less expensive than buying a new pair of boots.  (I'm always deeply saddened when I see discarded cowboy shoes out in the back alley that could have been saved just by a simple trip to a cobbler.)  Cowboy boots are an investment, they'll last forever if properly cared for.

Hopefully this hub has been of some use to you.  If you keep your accessory colors neutral you'll find a few simple country western shirts can give you a wide range of options for that classic cowboy look.  Please take a look at some of these links for ideas and store locations near you.