How to Pull Off the Cowboy Look for Men

My website has “made it” LOL!  I just discovered that the “eHow Style” website article by the title, “How to Pull Off a Cowboy Look for Men” used my Cowboy Boots and Jeans tutorial as a reference. That just cracks me up.

However, I can tell from all the internet searches that land visitors to that tutorial that a huge number of people look for that kind of information every.single.day.

Here’s my take on this question.

First, if you’re not a cowboy, then don’t be a pretender. The old Urban Cowboy fad-trend is long over. (In fact, anyone under 40 probably doesn’t know that I am referring to a movie that came out in 1980.)

Back on track… a lot of guys appreciate the relaxed, comfortable appearance of western wear. Jeans, t-shirt, ballcap, belt w/buckle, and cowboy boots… that’s it. Simple.

Belt with belt buckle? Sure … just don’t wear one of those “plate” buckles that rodeo cowboys wear (at the rodeo). A simple 2″ x 3″ rectangular or oval belt buckle, that perhaps shows the initial of your last name or has an interesting inlay design … that’s enough. In my opinion, don’t wear a buckle that advertises a brand of beer, boots, or cigarettes. That spells “dimestore cowboy” a mile away.

Stetson or Resistol cowboy hat? Really? You think cowboys wear 10-gallon hats regularly? Nope…. Perhaps for a semi-dressy occasion (as shown with a shirt and tie), or when actually riding a horse, attending a rodeo, or going to a stock show, you may see some guys wearing a traditional cowboy hat. Usually, when a cowboy hat is worn in warm weather, it is made of straw, because a straw hat is lighter and doesn’t get hot. Felt hats are warmer, heavier, and are worn in cooler months.

Most guys into the western-wear look (because that’s how they regularly dress) wear a ballcap. Yeah, a regular cap with a brim over the forehead, but not around the whole head. And don’t be silly — if you wear a ballcap, wear it with the brim facing forward, over your forehead — don’t wear it backwards. Again, guys who wear ballcaps backwards are fodder for ridicule because that’s just not how that kind of hat is worn by adult men. And note: most guys wear a hat. The sun in the U.S. Midwest and West is brutal on the scalp! Wear a hat for your protection and keep the sun off your head so you don’t fry your brains. Seriously. Hats help a lot in strong sunlight.

Boots? Well, there are a LOT of choices. Most guys wear plain leather cowboy boots, and occasionally exotic skins like ostrich, lizard, or python. Leather colors of black, brown, black cherry, or tan, and the boots have few accents or inlays. Usually you’ll find rounded toes, but the more pointed toes are not unusual. Heel height is usually a roper heel (1-2cm) or a walking heel (3-4cm). Cowboys (and those into the style) do not wear heels higher than that.

I have to be honest, lots of guys in my (former) home state of Oklahoma wear sneakers more often than boots. But if you really want the cowboy look, you gotta wear boots. And definitely not sandals or shorts!

Jeans? Regular Wranglers look great — or Levis, Carhartt, or Dickies — but not the cheap-o jeans from Walmart (they may be more affordable, but aren’t of good quality and often do not fit well.) Straight-leg regular blue denim jeans are most common. You don’t really need “boot cut” jeans but you can get them if you want more of a flare of your jeans over boots. Don’t get designer jeans, baggy, or low-rise jeans — definitely not “in” for Western style.

Get your jeans long enough to touch the tops of your boots, and gently fold on top of the boot, with the bottom of the leg in the back coming to the top of the heel. When jeans gently fold on top of the boot when you are standing, this is called “stacking” or “stacked jeans.” Don’t get jeans longer than that, ’cause you’ll trip, or shorter than that, ’cause it looks dorky.

And, guys, wear a belt. Nothing looks more ridiculous than seeing your underwear poking up around the back of your butt, or worse, your butt crack when you bend over. Have some dignity!

Tuck your jeans into your boots? Naaah… not really. I may do that for photos on my website, but when you look at guys who dress western on a regular basis, none of them wear pants or jeans tucked into their boots unless they are actually riding a horse or competing in a rodeo.

Shirt? As the referenced eHow-Style article says, a t-shirt is most common. While the article recommends a plain white t-shirt, I see lots of Western-style men wearing all sorts of t-shirts that have something printed on them. Your school, state, military branch of service, car or motorcycle brand, or supported charity — that’s all fine. A t-shirt that promotes drinking alcohol or has sexist or political statements on it is not a good idea. Nor are shirts that have various quotes (that shouldn’t be repeated on a G-rated blog). They tend to reflect poorly on the wearer (and really aren’t funny).

In cooler weather, a flannel or denim shirt is also a good choice. Many Western-style men wear shirts in all colors from blue to pink to red to yellow to green to purple. It really doesn’t matter, despite what the eHow or design/style guys say (IMHO!) Just one thing about shirts: make sure it fits, and tuck it in. Nothing looks more silly than a really baggy shirt hanging over a beer belly. Even bigger guys with some girth look better with a shirt that fits well and is tucked in.

As I began this post — many guys like the casual, comfortable style of western wear and like to “dress cowboy.” That’s fine, as long as you keep the look simple. It is easy to spot those who try too hard. You don’t need to. A ballcap, t-shirt, belt with a buckle, blue jeans and boots do the trick. That’s all you need.

Life is short: be comfortable in cowboy clothing.