Let’s be honest:
Buying a hat is easy. Buying a hat that actually looks good on you?
That’s the hard part.
Most people think they “just don’t look good in hats.” But 99% of the time, the problem isn’t your face. It’s that the hat doesn’t match your face shape.
We’ll show you how to find your face shape in 60 seconds. Then, we’ll tell you exactly which hats to buy and which ones to avoid.
How to Choose the Right Hat (The 30-Second Cheat Sheet)
Don’t overcomplicate this.
Most people fall into one of these 8 categories.
Look at the illustration below. Then, find the shape that matches your jawline and forehead width:
- Oval: Very balanced. It is slightly longer than it is wide with a rounded chin.
- Round: Soft and curved. Your face is about as wide as it is long, with full cheeks.
- Square: Bold and angular. You have a strong jawline and equal width from top to bottom.
- Heart: Wide forehead and high cheekbones that taper down to a narrow chin.
- Triangle (Pear): The opposite of Heart. A narrow forehead that widens into a strong jawline.
- Rectangle: Long and sharp. It has the length of an oblong face but the angular jaw of a square.
- Oblong: Long and narrow. Basically, your forehead, cheeks, and jaw are all the same width.
- Diamond: Unique and striking. You have a narrow forehead and chin with wide cheekbones.
Still not sure? That’s where the “Tape” comes in. If you’re stuck between two shapes, here is how to get a definitive answer.
How to Measure Your Face Shape (The 4-Step Method)
To get a definitive answer, you only need four simple measurements. Grab a flexible measuring tape and a notebook.
Pro Tip: Do this in front of a mirror. It’s 10x more accurate that way.
Step 1: Measure Your Forehead
Find the widest part of your forehead. Usually, this is halfway between your eyebrows and hairline. Measure from one side to the other and note it down.
Step 2: Measure Your Cheekbones
Measure across your cheekbones at their highest points.
Quick Tip: Start just below the outer corner of your eye.
Step 3: Measure Your Jawline
Measure from the bottom of your chin to where your jaw meets your ear. Now, multiply that number by 2. That is your total jawline measurement.
Step 4: Measure Your Face Length
Measure from the center of your hairline straight down to the bottom of your chin.
The “Widest Part” Rule
Here is the secret: Your face shape depends on which measurement is the largest.
- Face Length is the biggest? You likely have an Oval or Oblong face.
- Forehead the widest? You’re probably a Heart shape.
- Cheekbones are the widest? You have a Diamond face.
- Jawline is the widest? You have a Triangle face.
- All nearly equal? You have a Square or Round face.
Still unsure how to measure your face? Watch this quick video to see it step by step.
💡 Quick Shortcut
Don’t want to do the manual comparison? Plug your numbers into our Face Shape Calculator. It will tell you your face shape instantly.
Best Hats for Each Face Shape
Now that you know your face shape, here are the best hats for each one.
1. Best Hats for Oval Face
An oval face is the easiest to shop for. Your face is slightly longer than it is wide, which means most hat styles sit naturally without looking off.
But there are two styles to avoid: very tall crowns and very tiny hats.
Fedora. Works well because the brim sits naturally without looking too big or too small.
Baseball cap. Easy choice for everyday wear. Nothing awkward about it on an oval face.
Fedora vs baseball cap for oval face?
Both look good. Pick based on the occasion. If you’re going somewhere casual, a baseball cap is fine. If you want to look a bit more put together, go with the fedora. If you’re stuck choosing between the two, go with whichever complements your outfit.
Bucket hat. Relaxed fit, looks easy and natural.
Beanie. Pull it slightly back. Don’t push it all the way down your forehead, or it will cover too much of your face.
2. Best Hats for Round Face
Round faces are wider than they are long, with soft curves and full cheeks. The right hat adds a little height to balance that out and make your face look longer.
Fedora. The taller crown adds height, and the brim frames your face nicely. One of the best options for round faces.
Porkpie hat. Flat top with a short brim. The shape contrasts well with the softness of a round face.
Newsboy cap. Adds a little height at the front without looking too dressed up. Good for everyday wear.
Chunky knit beanie. Wear it high on your head, not pulled down tight. The extra height on top is what makes it work.
Wide-brim hat. The wide brim pulls attention to the sides and makes your face look less round.
Avoid: Round beanies pulled down low and bucket hats. They make a round face look even rounder. Small hats do the same. Just skip them.
3. Best Hats for Square Face
Square faces have a strong jawline and equal width from forehead to jaw. The goal is to soften those angles a bit. Hats with curves and soft brims do that well.
Bowler hat. The rounded crown softens a strong jawline naturally. Works well for both casual and dressed-up looks.
Bucket hat. The soft, relaxed brim takes the edge off a square face without trying too hard.
Cowboy hat. The curved brim works well here. It adds some softness without losing the boldness of a square face.
Floppy hat. The wide, soft brim balances a strong jawline really well. Good for summer looks.
Beret. Sit it slightly to one side. The soft shape contrasts nicely with sharp features.
Avoid: Boxy, stiff hats with flat brims. Match the angles of your face instead of softening them, and that makes your jawline look even stronger. Structured baseball caps with flat brims have the same problem. Just skip them.
4. Best Hats for Heart Face
Heart faces have a wider forehead and a narrow chin. The goal is to balance the top and bottom. Hats that add a little width at the bottom and don’t sit too high on the head work best.
Floppy hat. The wide, soft brim draws attention downward and balances a wider forehead really well.
Cloche hat. Sits close to the head and narrows toward the face. Balances the forehead without adding extra width on top.
Beret. Wear it tilted to one side, not straight on top. This takes some width away from the forehead and evens things out.
Medium-brim hat. Not too wide, not too narrow. Sits naturally without making the forehead the center of attention.
Trilby. The short brim and low crown keep the focus on the lower half of your face, which is exactly what a heart face needs.
Avoid: Tall crowns and wide brims that sit high on your head.
5. Best Hats for Diamond Face
Diamond faces are widest at the cheekbones with a narrow forehead and chin. The goal is to balance those wide cheekbones by adding a little width at the top and bottom.
Trilby. The short brim and medium crown sit nicely without drawing attention to the cheekbones.
Cloche hat. Fits close to the head and frames the face without adding width at the cheekbones.
Baseball cap. Sits naturally on a diamond face. The brim draws attention forward instead of sideways, which takes focus away from the cheekbones.
Beanie. Adds a little width at the top, which balances the narrow forehead. Don’t pull it too tight, or it will sit flat and make the cheekbones stand out more.
Pork pie hat. The flat top adds width where a diamond face needs it most, right at the top.
Avoid: Narrow hats and very tall crowns. They make the cheekbones look even wider by contrast.
6. Best Hats for Rectangular (Oblong) Face
Rectangle faces are longer than they are wide, with a straight jawline and similar width from forehead to jaw. The goal is to add some width and break up the length.
Wide-brim hat. The wide brim adds width to your face and breaks up the length. One of the best options for rectangular faces.
Bucket hat. The relaxed, downward brim adds width without adding any extra height. Works really well here.
Newsboy cap. The flat, wide top breaks up the length of the face and adds some width at the same time.
Flat cap. Similar to the newsboy cap. The wide, flat top works in your favor here.
Dad hat. Low profile and relaxed fit. Doesn’t add height, which is exactly what a rectangle face needs.
Avoid: Tall crowns and narrow hats. They add more length to a face that’s already long. Beanies pulled up high have the same problem. They make your face look even longer. Just skip them.
7. Best Hats for Triangle Face
Triangle faces are wider at the jaw and narrower at the forehead. The goal is to add some width at the top and draw attention away from the jawline.
Fedora. The wider brim and taller crown add width at the top and balance a strong jawline naturally. One of the best options for triangle faces.
Baseball cap. Adds width at the forehead and draws attention upward. Wear it slightly forward for the best look.
Floppy hat. The wide brim adds width at the top and softens a strong jawline at the same time.
Snapback. The flat brim sits wide across the forehead and adds the width a triangular face needs at the top.
Cloche hat. Sits close to the head and narrows toward the face. Draws attention away from the jawline without adding too much width at the bottom.
Avoid: Hats with wide brims that sit low on the head. They add width right at jaw level, which makes your jawline look even wider. Small hats have the same problem. Just skip them.
How to Look Good in a Hat
- Pick a hat that suits your face shape. That’s 80% of the work done. The rest is just fit and confidence.
- Make sure the hat fits properly. Too tight looks uncomfortable. Too loose keeps slipping. It should sit securely without pressing into your forehead.
- Choose a hat that complements your outfit. A baseball cap looks out of place with a formal outfit, and a fedora looks off with a tracksuit. Think about where you’re going and dress the hat accordingly.
- Wear it with confidence.
Not sure how to wear your hat the right way? We cover that here.
Final Thoughts
There aren’t any strict rules to find the right hat; it’s all about balance and comfort. Once you understand your face shape, you’ll start to notice which styles naturally suit you.
Try different hats, see what feels right, and don’t overthink it. In the end, the best hat is the one that feels natural and gives you confidence when you wear it.
P.S. If you find a style you love but hats always feel too tight on your head, check out The Headroom Method for Big Head Hats. It’s the easiest way to find a fit that actually feels comfortable all day.
