How to Dress Like a Cowboy: 5 Steps

**This post, minus a few updates, was originally published in 2011 on another blog I managed, but its popularity led me to share it with you too.**

The following is a a brief guide for guys on how to dress like a cowboy.  It is meant to help you choose what to wear to a rodeo as a spectator. You can wear whatever you like, of course, but if you want to be virtually indistinguishable from the guys competing in the arena, there are some important fashion “rules” that should be adhered to.  I have broken them down into 5 key areas:

1.) Hat

A cowboy hat is serious business.  If you are “in the know,” you can determine many things about a cowboy, by looking at his hat,  including where he lives, what event he competes in, and most of all, whether or not he’s a “real” cowboy (or at least knows how to dress like one).  The two main considerations here are material and shape.  Felt hats are normally going to be more expensive than straw hats, and it is my recommendation that if you are going to spring for a felt hat, get a pretty good one made by a reputable hat maker.

By pretty good, I mean some sort of a beaver  or rabbit blend rather than a wool felt.  It will last longer and look better in the long run (and in the short, for that matter).  Hat quality is determined by the number of “X’s” a hat has, however there is no industry standard for “X’s” so one company’s 10X could be another company’s 20X.  Go with around a 6X or better from a company like Resistol, Stetson or American Hat Company and you should be fine.

If you don’t want to spring for a quality felt, get a nice looking straw hat. They tend to be a much cooler (temperature-wise) option for the summer too.

If proper fit is a concern for you, consider a custom hat. Companies like Greeley Hat Works will build you a one-of-a-kind masterpiece that fits your odd-shaped head like a glove.

2.) Boots 

Equally important to what you sport on your head is what you choose to put on your feet.  You won’t see too many cowboys wearing lace-up boots these days, and pointy toed boots or “cockroach killers” on a guy aren’t going to cut it either.  A simple roper-style boot with a flat heel and a round or square toe (square toes are very “in” right now) is your safest bet. The taller riding heel is nice looking but less practical if you will be doing more walking than riding. Most people will find the flat heel more comfortable.

Once you get the basic style down, there are hundreds of options in colors, materials and price point.  Expect to pay anywhere from $130 for a standard, basic leather boot, up to more than $500 for exotics like ostrich and caiman.  Oh, and no matter how pretty the tops of your boots are, your jeans should go over them, not the other way around.

*Note* When I originally published this post I got some flack over that last recommendation. Please understand, I am not saying jeans should never be tucked into boots, I am simply recommending that for the sake of “blending in at a rodeo,” it is best to wear your jeans over your boots. Nothing says “I am trying way too hard” like a brand new shiny pair of boots on display for the world to see. If you’ve got the cowboy prowess to back it up, by all means do whatever you want.

3.) Belt

This is a tricky area. A trophy buckle on a cowboy is proof to the rest of the world that he can carry his weight in the arena. A nice custom-designed silver 3-piece buckle says, “I may not have won this, but I am enough of a cowboy to know what looks good holding my pants up.”  Pretty much any other kind of purchased western belt buckle (with a few exceptions) screams, “I am not a real cowboy!” Sporting a genuine trophy buckle that someone else won (while some may disagree with me on this) is perfectly acceptable in my book, because if you’re dressed well otherwise, nobody is going to know the difference. Borrow one from a cowboy friend, or check the pawn shops or ebay. Remember, retro is in, so “1956 Champion Saddle Bronc Rider” works, even if you weren’t yet hatched. . . could have been your dad’s, uncle’s or grand pappy’s.

If a trophy buckle isn’t an option, my best advice is to keep it simple, and avoid drawing a lot of attention to the area.  If you still want a silver buckle, I would recommend a tasteful and simple 3-piece style (Vogt makes some really nice ones).  Nothing with writing on it.  As mentioned previously, a “fake” trophy buckle can be spotted a mile away.  Custom-designed silver buckles with initials or a personal brand are totally different (and a great choice), but we won’t get into it here.

In the interest of cost and wearability, your best bet might be to just buy a simple leather belt, like the one shown here made by Ariat, that comes with a tasteful buckle. If your boots are brown, buy a brown belt. It doesn’t necessarily need to be the same shade. Same thing goes for black. You can even find belts that are black and brown to wear with either color boots.

Leather belts only, please!  Do not try to bring back the nylon belt trend of the 80′s and 90′s. Also, you will notice the girls wearing a lot of “bling” aka “sparkly things” on their belts. Some companies are making sparkly belts for guys too. Personally, I am not a fan of bling on dudes. A few crystals might be ok, and of course it is up to your discretion, but I would advise against it. A little silver (even a lot) is great, just stay away from the swarovskis.

4.) Jeans

When it comes to jeans, I would recommend sticking with a signature western brand like Wrangler, 20X (a division of Wrangler), or Cinch.  They come in a plethora of different styles these days, and the style isn’t all that important as long as the fit is right.  Just make sure they aren’t too tight (the skin-tight look went out in the 80′s) or too loose (there’s no “sagging” in rodeo) and that they are long enough.

Length may be the most crucial part of selecting a good pair of jeans.  Remember, you are going to be wearing them over your boots, so they need to be longer than what you would normally buy to wear with shoes.  They need to “stack” a little bit so that they still cover the tops of your boots when you are sitting down. If you typically wear a 32″ inseam, you might want to buy a 34″.

If you really want to look the part, take your jeans to the dry cleaners (or click here to learn how to do it at home) and have them heavy starched.  It will make you look sharp and authentic.

5.) Shirt

Last but not least, the “cowboy shirt,” as my brother referred to them when he was little.  A nice button down, whether long sleeved or short will look the best.

My general recommendation is to stay away from western t-shirts.  There are some really bad ones out there.  Like this one. But there are a few cool western t-shirt companies out there now that I can recommend. If you are a dyed-in-the-wool t-shirt guy, check out sayiwont and Cowboy Militia. These brands are Earn Your Spurs approved. ;-) Cinch, Wrangler and Ariat have some nice logo t-shirts that are ok too.

Ultimately, I recommend the classic button-down western shirt. If you’re getting your jeans starched, go ahead and do your shirt too, and add to your clean, pressed look.  At the very least, take an iron to your shirt.  It just looks so much better. Like you actually put some thought into your appearance and didn’t just roll out of bed to go to the rodeo.

Retro styles are very popular right now, but I would be a little careful with those. Some are your basic “plaid with pearl snaps” numbers which are fine, others have some pretty funky graphics. You can never go wrong with a classic print. A shirt like the one pictured never goes out of style and always looks great.

For best results, stick with the five basics above.  Leave the bolo ties, bandanas, spurs, chaps and any other unnecessary accessories at home.  They are either inappropriate for the setting or just wrong in general. Plus, the more items you try to work into your ensemble, the greater chance you have of a direct violation of the cowboy dress code, which is what we are trying to avoid here.

Now that you look the part, you just need to come up with a good story for the first person who asks you where you parked your pony.  And remember, chicks dig cowboys, so the more authentic you look, the better chance you have of collecting a phone number or two before the night is over.  Don’t worry, you can thank me later.

If you have questions or other suggestions, leave a comment below!