Tips for Styling Your Western Cowboy Hat

Ranchers and wranglers wear cowboy hats for many reasons: shade, warmth, protection from the elements, to fan a fire, or to wave at other cattlemen from horseback. But you? You will wear it because you can. With the right tips for styling your western cowboy hat, you can effortlessly amp up your aesthetic.

Choose Your Weapon

There are an endless variety of cowboy hats, and the right one is waiting for you. To use a wizarding metaphor, you are Harry Potter looking for the wand of his destiny. Try different sizes and styles—there’s “the gambler,” “the pinched front,” “the derby,” “the cattleman,” and more modern interpretations. John Stetson wasn’t born a cowboy—he was from New Jersey, the son of a hatmaker, and came up with the design for his signature Stetson in 1863, somewhere on Pike’s Peak. You have every right to find your perfect fit with both feet firmly on the ground.

Felt hats are dressier, while straw hats are appropriate for everyday wear. Look for something that doesn’t overwhelm you, and complements your face shape. You might recognize the right hat by its buckle, or details like crystal embellishments, or a suede weave.

Ignore the Naysayers

Don’t ask others if you should buy a cowboy hat; they will say no, and even use phrases like “lumbersexual” and “all hat, no cattle.” They are wrong. The only advice you need comes from Dudes Boutique. You can add flair without going over the top. A cowboy hat says that you are confident, rugged, and your own man.

Start with the Basics

Don’t wear it backwards. Many hats have a small bow on the lining inside, around the headband. Make sure the bow is at the back of your head, or that it’s narrower in the front. The low point of the hat is at the back, with the high point at the front. Even if the other city slickers won’t be able to tell the difference, you’ll know.

Work the Angles

There’s a language for the brims of cowboy hats, so be sure you’re saying what you mean. A level brim indicates a straightforward, from-the-hip attitude. Tipping it down over your eyes gives you an air of seriousness with a hint of mystery. You can tilt a cowboy hat slightly to the side for rakish confidence but be careful—people may think you’re looking for love… or trouble. Don’t push the brim up too far, unless you want to appear really, really friendly.

Dress Strategically

If you live anywhere other than Texas, you don’t want to overdo the western wear, or you can look like you’re wearing a costume for a barn-themed rave. Choose the rest of your outfit in relation to the hat. You can’t go wrong with a plain white T-shirt layer. If you want to wear boots, avoid anything too overtly cowboy. Solids, plaids, flannels, and sweaters are natural under a hat.

For outings that are just a bit dressier, you can wear your cowboy hat with a blazer for that pro-athlete-in-town-for-the-game look. But if you’re pairing it with jeans, the only way to go is straight leg, without any details that can detract from your intended focal point. Avoid jeans that are:

  • Dramatically skinny-leg
  • Flares
  • Low riders
  • Floods
  • Cuffs
  • Bleach stains
  • Stone wash

Show Some Restraint

Only you will know when too much is too much, but you can’t go wrong with a “less is more” attitude. If your ensemble gives you a fresh-from-the-range twang, pull back a little. Wear one western-inspired item at a time, so admirers will know where to look first. At Dudes Boutique, we generally aren’t about fashion don’ts, but first-time cowboy hat wearers may want to avoid:

  • Chaps
  • Studs
  • Dusters
  • Fringe
  • Mullets
  • Chewing tobacco

Statement belts always add to an outfit, but when worn with a cowboy hat, they can be too much competition. Steer clear of blingy rodeo belts and buckles, or anything approaching the grandeur of a wrestling championship belt. You may be wearing it ironically, but not everyone will get it.

Warning: A bandana? Let’s not. You are not John Wayne, or even Woody from “Toy Story.” Don’t even wear a bandana even as a mask with a cowboy hat.

Look to the Style Icons

Whole-hog western trends come and go, but real men look great in cowboy hats no matter the era or the occasion.

No: “The Electric Horseman,” “Midnight Cowboy,” “Back to the Future Part 3”

Yes: “Butch Cassidy and the Sundance Kid,” “Unforgiven,” “No Country for Old Men”

Advanced: “Easy Rider,” “Brokeback Mountain”

Sam Elliott is a natural in a cowboy hat, while Elton John achieves a very different effect. Know who you want to be. But if you’re going for “Marlboro Man,” don’t accessorize with a cigarette.

Remove When Appropriate

Cowboy hats invoke tradition, and in the west, there is specific etiquette for them. Use your best judgment, but you should at least know the cowboy code. It’s about respect, but resist the urge to say “howdy” or “ma’am” when you’re taking off your hat. Here’s when it’s not considered tasteful to keep your hat on:

  • In church
  • In the presence of the flag (place it over your heart)
  • In a private home
  • During an indoor wedding
  • During an introduction
  • When greeting a lady
  • When a casket is passing by
  • At the table (it can stay on if you’re eating at a counter)
  • When pearls are being clutched

Adopt Manners Befitting the Hat

If you’re going to go western, you need to walk the walk—and we don’t mean the bow-legged walk that comes from riding a horse. The style comes with the behavior of a southern gentleman who believes in courtesy and respect. You should have the demeanor of a cowboy who has had a long, dusty day herding high-spirited cattle, and has been presented with a heaping plate of down-home grub. Or just imagine that you’re talking to your mama.

You can keep it real—and keep it rugged—with some tips for styling your western cowboy hat that emphasize you, not a cosplay alter ego. At Dudes Boutique, we offer a selection of choice hats that will put you head and shoulders above the rest. As a men’s clothing boutique with a legendary reputation 20 years in the making, we know how to elevate your look with one-of-a-kind pieces. Contact us for more information.

Tips for Styling Your Western Cowboy Hat



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