how to pick a cowboy hat

How to Pick the Perfect Cowboy Hat: A Comprehensive Guide

by | Aug 3, 2023 | Apparel, Equestrian Clothing

The cowboy hat – it’s not just a hat, right? It’s a chunk of Western culture you can stick on your noggin, a practical and good-looking bit of gear. Shades your eyes, shields you from the weather, and makes you look darn good. Plus, for many of us, it’s a way of life, a show of individuality, a nod to the wild, wild West. So, picking the perfect cowboy hat, well, it’s not just shopping. It’s an art.

Choosing the right cowboy hat isn’t just about grabbing the first one that makes you say, “wow!”. Nah, there’s a lot more going on. You gotta think about how it matches up with your face shape, personal style, and what you’re gonna be using the hat for. Not just looking pretty – although that’s a perk. In this no-nonsense guide, we’re gonna break down the ins and outs of picking a cowboy hat that’ll make you look like a million bucks.

Let's Talk Cowboy Hat Styles

Here’s the thing: cowboy hats ain’t one-size-fits-all, and I ain’t talking about hat size. I’m talking about style. Some hark back to the days of riding into the sunset, with a broad brim, high crown, and no frills. Take the Stetson Open Road Hat, for instance. But there’s also the modern twist on the cowboy hat, like the Stetson Skyline Hat – traditional but with a fresh spin. And then, for the daring, there are the fashion-forward cowboy hats, pushing the envelope with bold colors, interesting shapes, and anything-but-ordinary embellishments. Think Charlie 1 Horse Highway Silverbelly.

Each style’s got its own vibe, and you’ll wanna match it up with yours. Maybe you’re a sucker for the classics, or you love the mix of old and new. Or perhaps you’re all about making a statement. Understanding where you fall in the style spectrum can help you nail down the hat that’s gonna suit you best.

Matching Cowboy Hats and Face Shapes

Now, let’s chat about face shapes. When it comes to picking a cowboy hat, your face shape matters. The right hat can make you look like John Wayne in his prime, while the wrong one might leave you looking more like Yosemite Sam.

John Wayne in Hondo

John Wayne in Hondo

Here’s a bit of a cheat sheet:

1. Oval Faces – If you’ve got an oval face, lucky you! You can pull off just about any hat. Go with a high-crowned hat for a classic look or try something more out-there for a bit of fun.

2. Round Faces – If your face is round, a high crown and tilted brim, like the Scala Classico Western Hat, can help give you a bit of edge and balance.

3. Long Faces – Got a long face? Opt for a medium crown that sits low on your forehead. The Stetson Gus Hat is a great choice – it won’t make your face look any longer than it is.

4. Square Faces – Square face? A wide brim and a soft, rounded crown, like the Bailey Western Wind River Maverick Hat, can soften those angular features.

5. Heart Faces – If your face is heart-shaped, go for a smaller brim and a not-so-high crown, like the Charlie 1 Horse Gold Digger Hat, to balance that wider forehead.

6. Diamond Faces – If your face is diamond-shaped, a moderate to wide brim with a low crown works best. The Resistol George Strait Kingman Hat is a stellar choice – it can lengthen your face a bit, for a flattering look.

Okay, you’ve got the basics down pat now: what a cowboy hat stands for, what style vibes with you, and how to match a hat to your face shape. But we’re just getting started. Let’s mosey on to some more specifics.

Determining the Right Brim Size for Function and Style

We’ve got a lot to consider: brim size, material, and fit. It’s like a three-legged stool, and if one leg’s off, well, you’re in for a tumble!

First up, brim size. You may not realize it, but this ain’t just about style; it’s a balancing act between lookin’ good and staying practical. Take a gander at the hats worn by cowpokes working under the sun – they’ve got large brims to shield their faces from the harsh weather. However, if you’re more of a city slicker or hitting a shindig in town, a trimmer brim might just hit the spot.

You know George Strait, right? His namesake hat from Resistol sports a medium brim, kind of like a ‘jack of all trades’ situation. And then there’s the Bailey Caliber Wind River outback Hat – with a wider brim, you might say it’s as protective as a mama bear with her cubs.

But hey, don’t just think about where you’re wearing it. Think about who’s wearing it – you! If you’re blessed with a rounder face, you might want to go with something like the Stetson Wool Gambler – it’s got a higher crown and slanted brim that’ll make your cheeks look as sharp as a Bowie knife.

Materials Matter: Choosing the Right Material for Your Cowboy Hat

Next up is materials. You wouldn’t wear a fur coat to the beach or flip-flops in a blizzard, would you? The same principle applies here. Felt hats are like your trusty flannel shirt – sturdy and warm, perfect for when the leaves start turning. Straw hats, on the other hand, are your summer best friends – light, breezy, and they won’t cook your noggin like a baked potato. If you’re going for a rough-and-tumble look or need something as tough as old boots, you can’t go wrong with leather.

Getting the Fit Right: Ensuring Your Cowboy Hat Fits Perfectly

And last, but certainly not least, we’ve got the fit. If it doesn’t fit right, you’ll be fiddling with it all day, and that’s no fun. A cowboy hat isn’t a cap – it should be snug, but not so tight you’re getting a headache. It’s gotta sit right and stay put whether you’re riding a bronco or busting a move on the dance floor.

The Stetson Men’s Wool Felt Crushable Western Hat is one solid option. Sizes aplenty and fits like a dream. Or take a look at the Ariat Men’s Bangora Western Hat. Adjustable band means you can get it just right, kinda like the Goldilocks of hats!

But what if your hat is giving you a squeeze, or maybe it’s a little too breezy up top? No worries. You can try a hat stretcher, or add some foam tape to tighten things up. Remember: it’s your hat, it should feel like a part of you. It should be snug enough to stay put, but not so tight that it’s cramping your style.

Adding Personality: Understanding Cowboy Hat Details and Customizations

Cowboy hats are a lot more versatile than people think, and can be jazzed up with a host of cool additions that scream ‘you’.

We’re talking about everything from cool bands and buckles to feathers (that’s right, feathers!) and some really fine hand-crafted patterns on leather. And oh, you can also toy around with the brim and crown shapes.

Now when you’re deciding on the hat accents, you gotta ask yourself – “What’s my vibe?” If you’re the kinda person who digs the old-school charm, then a neat leather band or a slick silver buckle might just do the trick. But if you’re more of a peacock and want to strut your stuff, why not opt for hats with fancy embroidery, vibrant feathers, or some detailed beadwork?

Just to throw a couple of suggestions your way, the Stetson Skyline Cowboy Hat is a safe bet for its minimalistic charm. But if you’re more of a ‘make a statement’ type, the Montecarlo Bullhide Toyo Straw Hat with a catchy beaded band might just tickle your fancy.

Cowboy Hat Etiquette: Wearing and Caring for Your Cowboy Hat

We gotta talk about cowboy hat etiquette – yes, that’s a thing. It’s usually polite to take your hat off indoors, during the National Anthem, or when talking to a lady. And remember to handle your hat by the brim, not the crown, unless you fancy a warped hat shape.

A cowboy hat can last you a good while if you treat it right. That means storing it in a cool, dry place away from Mr. Sun and giving it a gentle clean now and again with a soft brush or a damp cloth.

And where to sport this beauty, you ask? Cowboy hats are a perfect fit for outdoor events like rodeos or country music gigs, or even a casual day out. But remember, these might not be the best fit for black-tie affairs or indoor gatherings, unless of course the dress code calls for it.

And just a little gentleman’s tip – it’s seen as respectful to take your hat off in a place of worship, during grub time, or when meeting someone for the first time.

Related: The Best Horse Riding Jeans for Men and Women: Comfort, Durability, and Style


Alright, here’s the wrap-up. This ain’t rocket science folks, but finding the perfect cowboy hat boils down to your personal style and comfort. You might be a Stetson guy or a modern straw hat gal, the key is that the hat should scream ‘you’ and feel as comfy as a well-worn pair of jeans.

And above all, this should be fun, amigos! Take your sweet time trying on different styles, fiddling with the details, and making the hat yours. And remember, good things come to those who wait. So keep at it, and before you know it, you’ll have found a cowboy hat that fits like a dream and becomes a key part of your personal style. Now, ride off into the sunset, cowboy!

About The Author

<a href="" target="_self">Emily Wilson</a>

Emily Wilson

I'm from the very heart of Kentucky, you know, the place folks think of when they talk about horse love. Had the luck of growing up smack dab in the middle of some of the most awesome horse spots you'd ever see. Can't imagine starting my day any other way than being in that homely barn, waist-deep in horse stuff. My routine? It's a bit of everything really - taking care of the horses, bonding with them, you name it.

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