Most people wear a cowboy hat completely wrong. The fit looks off, the angle doesn’t match their face shape, and the basic rules get ignored. Wear it the right way, and it instantly looks natural and stylish.
In this guide, you’ll learn exactly how to wear a cowboy hat correctly, how it should fit, how to tilt it, and which styles actually work for your face.
Cowboy Hat Basics
Before we dive into fit, style, and care, there are a few things every cowboy hat wearer should know:
- Fit matters: The hat should sit snug but not tight. Too loose and it shifts. Too tight and it’s uncomfortable.
- Front matters: Never wear it backward. The hat has a front for a reason.
- Tilt carefully: How you tilt your hat depends on your face shape. A subtle tilt works; too much looks awkward.
- Indoor rules: Take your hat off in homes, churches, and formal settings. It shows respect.
- Seasonal tip: Straw hats are best for summer. Felt hats work better in colder months.
How a Cowboy Hat Should Fit
Getting the fit right is the single most important step. A cowboy hat that’s too tight will give you a headache. Too loose, and it will slide or blow off in the wind. Here’s how to make sure it sits perfectly:
Measure Your Head Correctly
Wrap a soft tape measure around your forehead, just above your ears. That’s your hat size.
If you’ve got a bigger head and regular sizing still feels tight or awkward, our The Headroom Method for Big Head Hats shows you how to fix that.
For instant accuracy, you can also use our hat size calculator, which tells you exactly what size to pick so your hat sits snug without being too tight.
Check the Crown Fit
The crown should sit comfortably on your head. You want a snug hold without any pressure points. A properly fitted crown keeps the hat stable and looks clean.
Align the Brim
The brim should sit just above your eyebrows. Too low, and it hides your face; too high, and it looks awkward. The right alignment frames your face naturally.
Test the Movement
Shake your head lightly. The hat shouldn’t wobble or slip. If it does, adjust the size or try a different style.
Pro Tip: Don’t guess your size. Measure first, then try it on. Even the most stylish hat will look off if it doesn’t fit properly.
How to Wear a Cowboy Hat Correctly (Step-by-Step)
Most people wear a cowboy hat wrong. It sits too high, too low, tilted weirdly, or just off balance. Following the steps below will ensure you know the right way to wear a cowboy hat every time.
Step 1: Prepare Your Hair
Your hair matters.
Short hair should be neat so the hat sits properly. Long hair should be tied low or fall naturally under the crown. Don’t pile it on top because it pushes the hat up and changes the fit. Women can go with simple waves, braids, or a sleek ponytail.
For more tips on long hair, see our guide on how to wear hats with long hair.
Step 2: Identify the Front and Back
Most cowboy hats have a small bow or tag inside the sweatband marking the back. If there isn’t one, the front is usually narrower and curves downward. Wearing the hat backwards looks careless and shows you don’t know the proper cowboy hat etiquette.
Step 3: Position the Hat on Your Head
Hold the hat by the crown, not the brim, to avoid bending it. Place it about an inch above your eyebrows. Make sure it rests comfortably around your ears and feels balanced.
The hat should not be too tight or too loose. If you’re not sure about your size, try our hat size calculator to find the perfect fit.
Step 4: Adjust the Angle
A slight tilt can add style. Tilt it up slightly for a friendly look, down for a tougher appearance, or slightly to the side to add personality.
Too much tilt in any direction looks off. Match it with your face shape: round faces tilt slightly forward, square faces slightly backward, oval faces can handle most tilts.
Step 5: Check the Fit
Move your head lightly. The hat should stay in place without pressure. If it shifts or feels loose, it’s too big. Many hats have adjustable bands inside, or you can use sizing tape or foam inserts to tighten them. A properly fitted hat looks natural, stays in place, and can be worn all day comfortably.
Cowboy Hat Shapes and Styles
Not all cowboy hats are the same, and the shape really changes how the hat sits, how it feels, and how it makes you look. Pick the wrong one, and even a perfect fit can look off.
Cattleman
This is the classic cowboy hat, the one you probably picture in movies. It has a tall crown with a crease down the center and small dents on the sides.
It’s simple, versatile, and works for almost every face. We usually recommend this style to anyone starting out because it’s hard to go wrong with it.
Gus
The Gus is bolder. Deep crease, high points on the sides. It stands out, so it’s perfect if you want a more dramatic western look.
Long or square faces handle it best. We’ve noticed that people who want to make a statement tend to gravitate toward this style naturally.
Brick
The Brick has a flat top and straighter edges. It looks sharper and cleaner than other styles. Round and oval faces wear it best. You’ll see this style a lot at shows or western events when someone wants a modern take on a classic hat.
Gambler
The Gambler has a flat crown and a wide, slightly curled brim. It’s casual and relaxed. We like this one for outdoor gatherings, music festivals, or anytime you want a laid-back look without looking sloppy.
Face Shape Tip: Round faces do better with a taller crown. It adds length. Square faces need a medium crown and a slight tilt to balance strong angles. Oval faces can wear most hat styles.
Material Matters
Straw is lightweight and breathable, perfect for hot days or long hours outdoors. Felt keeps your head warm in cold weather and is better for formal occasions.
Leather can go year-round, but it’s not common for dressier settings. We’ve found that choosing the right material often matters more than the style itself when it comes to comfort.
Choose a hat that fits your face, fits your lifestyle, and suits the occasion. Even a great hat can look off if it doesn’t feel right when you put it on.
How to Pick the Right Cowboy Hat for Your Face Shape
The right cowboy hat can change how your face looks. Pick the wrong one, and it can feel off, even if it fits well. Here’s how to choose the right hat for your face.
Round Faces
Choose taller crowns and sharper creases. They add height and make the face look longer. Flat crowns or wide brims make the face look wider. Cattleman or Gus styles work best.
Square Faces
Medium crowns and slightly curved brims soften a strong jawline. Brick hats or Cattleman styles with subtle dents work well. Avoid flat or boxy crowns.
Oval Faces
Most hat styles work for oval faces. Focus on balance and proportion. Cattleman or Gambler styles are safe choices.
Heart Faces
Heart-shaped faces have a narrow chin and a wide forehead. Wider brims balance the face, and moderate crowns keep it proportional. Gambler or Cattleman styles work best. Avoid tall crowns.
Long Faces
Low or medium crowns with slightly curved brims work best. Brick or Gambler styles keep the face in proportion and stop it from looking longer.
Most people are not sure about their face shape, and that’s normal. If you want a quick way to figure it out, use the face shape calculator. It will tell you your shape so you can pick the right hat without guessing.
Face Shape Cheat Sheet
| Face Shape | Best Cowboy Hat | Why |
|---|---|---|
| Round | Cattleman, Gus | Adds height and structure |
| Square | Brick, Cattleman | Softens jawline and angles |
| Oval | Any | Most hats fit naturally |
| Heart | Gambler, Cattleman | Wide brim balances narrow chin |
| Long | Gambler, Brick | Low crown keeps proportions balanced |
Cowboy Hat Styles and When to Wear Them
Different materials handle different situations. Pick the right one and your hat will feel like it was made for the moment.
Felt Hats
Felt works best in the fall and winter. It holds its shape and looks a little sharper. Most people wear felt for cold weather, rodeo events, nights out, and anything semi-formal. It pairs naturally with denim jackets, flannels, button-downs, boots, and darker outfits.
Straw Hats
Straw is made for heat. It’s light, breathable, and ideal for summer, outdoor work, or long days in the sun. It fits well with simple tees, light denim, plaid shirts, and any casual warm-weather outfit.
Leather Hats
Leather can take rough use. It works almost year-round and handles wear better than straw. It looks best with rugged clothes, work jackets, boots, and anything built for the outdoors.
Palm Leaf Hats
Palm leaf is a tougher version of straw. It’s great for hot weather and handles sweat and sun without breaking down fast. It works well with summer shirts, breathable tops, light jeans, and outdoor casual outfits.
Seasonal Tip: Use straw when it’s hot, felt when it’s cold, and leather when you want something you can wear most of the year.
Cowboy Hat Etiquette: The Basics You Should Know
Cowboy hats come with a few unspoken rules. Nothing complicated, but they matter. You don’t need the full history lesson here, just the essentials. Following these cowboy hat rules ensures you look confident and respectful.
When not to wear a cowboy hat?
Take your hat off indoors, during meals, or during prayers. At weddings, funerals, and formal events, remove it unless everyone else keeps theirs on. If you’re unsure, just take it off—this always works.
Tipping your hat
Tipping the hat is a quick greeting. A small lift or a light touch on the brim is enough. Don’t overdo it. A lot of people ask: What does it mean when a cowboy tips his hat? Simply, it can be a polite greeting, acknowledgment, or a sign of respect to someone. It’s a small gesture with clear meaning.
Bars and casual places
Most country bars don’t follow strict rules. You can keep it on while dancing or hanging out. At sit-down tables or restaurants, it’s polite to remove it.
Straw vs felt
People still follow the old rule. Straw in warm months. Felt in cold months. Weather matters more than tradition, so use whatever makes sense.
Respect other people’s hats
A cowboy hat is personal. Never grab someone else’s hat. Ever, if you’re curious about it, just ask.
Cowboy Hat Mistakes You Should Avoid
A lot of beginners slip up on the basics. The biggest one is wearing the hat backwards. It throws off the whole look and makes it clear you didn’t check the front and back.
Another common mistake is over-shaping the brim. If it’s curled too much or has a dramatic bend, it looks forced. Keep the shape clean and natural.
Wearing a cowboy hat with sneakers or loud streetwear usually looks off unless you really know how to style it. Most people don’t, so keep the outfit simple.
Fit is another big one. A hat that’s too tight or too loose never looks right. Get your size right before anything else. If you’re not sure about your exact head size, learn how to measure your head correctly to avoid these issues and get a hat that actually fits.
And one more thing. Don’t show the inside of your hat when you take it off. The sweatband is personal, and turning it toward people is considered bad manners.
How to Wear Your Cowboy Hat with Confidence
Get the fit right. Pick a style that suits your face. Keep it natural with the right angle and material. Pair it with simple outfits. Do this, and your cowboy hat will always look like it was made for you.
If you’re not confident about your hat fit yet, you need to check our guide on how to wear a hat the right way. It will save you from common mistakes.
FAQs
Can I wear a cowboy hat if I’m not a cowboy?
Yes, you can. You don’t need to be a cowboy to wear one. The important part is wearing it the right way. Make sure it fits well, complements your outfit, and follows the basic etiquette. If it sits right and looks natural, people won’t care whether you ride horses or not.
Do I wear the high or low point of the cowboy hat at the front?
The low point goes in front. Most cowboy hats have a bow or tag inside the sweatband that marks the back.
How to wear a cowboy hat while driving?
It’s fine to wear a hat while driving if it fits well. Make sure it doesn’t block your view. If it has a string, adjust it lightly so it stays secure. Don’t tip it while driving.
How to wear a bandana under a cowboy hat?
Fold the bandana into a triangle and tie it around your head with the knot at the back. Make sure it sits comfortably on your forehead. Put your cowboy hat on over it so it fits naturally. The bandana should not make the hat tight or change its shape.
