A lot of people struggle to find a hat they feel confident enough to wear, which is unfortunate because hats are one of the greatest accessories you can have. They work with almost any outfit and can be used to dress up or dress down whatever you choose to wear. If you don’t like the hat you wear, though, or you think it looks weird on you, then you’re less likely to wear one.
People who don’t feel confident in hats are typically making the same mistake: They aren’t picking a hat that’s right for their face.
You may not realize it, but face shape plays a huge role in how a hat looks on you. Once you know how to pick the right big hat for your face, you’ll feel much more confident in your choice of headwear and will be able to add the perfect finishing touch to your outfit without worrying.
3 Ways to Pick the Right Hat For Your Face
#1. Know Your Face Shape
The very first step to picking out a hat can actually be done from home. First thing’s first, pull your hair back away from your face so that you can see your whole face. Use a hair tie to make this as easy as possible since you’ll probably want your hands free. You’ll also want to wear a shirt that doesn’t cover your neck as this can impact what your face shape appears to be.
Perhaps the easiest way to figure out your face shape is with a dry erase marker and a mirror. If you have both, great! Make sure your mirror is stable, either hanging up or standing on a desk, and then draw the outline of your face in the mirror.
There are two other ways to do this: with a foggy mirror or with an old photo. With a foggy mirror, trace the outline of your face and take a photo of the result before the drawing disappears. If you have an old photo of you looking directly at the camera, then you can use it to draw around the outline of your face.
Once you’re finished, here are a few questions to ask yourself about your face:
- Is my forehead wider, narrower, or as wide as my jawline?
- How wide are my cheekbones in comparison to my forehead or jawline?
- Is the length of my face similar to the width or much different?
Round Faces
Round faces are almost as wide as they are long. Features characteristic of round faces include round jaws and hairlines.
Heart-Shaped Faces
With a heart-shaped face, your forehead and cheeks will be wider than your chin, which is often more pointy than round.
Square Faces
If you have a square face, then your jaw will look like it follows a straight line up to your forehead. You may have a minimal curve to your cheeks and your face width will be similar to your face length.
Diamond Faces
Diamond faces have cheeks that are wider than their foreheads. Chins tend to be narrow, but often with a strong point. These faces look longer.
Oval Faces
With an oval face, your cheeks and jawline will be a similar width. Your forehead will be barely wider and your face will be longer than it is wide.
#2. Identify Your Skin Tone and Undertone

Knowing your skin tone and undertone is important for more than just finding the right hat. It will help you pick out better colors to wear and let you know what color palettes tend to look best with your natural skin color.
To pick the right hat, you need to know what will look good with your skin, so take the time to examine your skin and identify your skin tone and undertone.
If you’re unable to come to a conclusion that way, then you can visit a nearby cosmetic store and ask them to do a tone match for you. Not only will you get a better idea of whether you have cool or warm tones, but you’ll also learn which foundation and makeup will look best with your skin!
#3. Learn What Colors Look Best With Your Skin Tone
Lastly, you need to know what colors will look good when you wear them or you’ll never wear your hat. Now that you know your face shape and skin tone and undertone, you’re ready to pick out the color that matches you best.
If you came to the conclusion that you have a warm skin tone, then colors like honey, olive, peach, and cream will look great on you. Pick colors on the red-orange side of the color wheel, but don’t shy away from a warm brown or green.
For those with a cool skin tone, stick to the blue-white side of the color wheel. You’ll look great in gray, blue, lavender, and white. If you want something warm, you can try a deep red or pale yellow.
Neutral skin tones look great in any color, but you may want to choose more muted colors than bright colors that may clash.

Pick Out Your Hat!
Now that you know so much more about your face, it’s time to pick out your hat! Depending on your face shape, you’ll look better with different styles.
Round faces should pick hats with a tall crown to add height to their face. Fedoras are the perfect option and they look great with anything!
Heart-shaped faces should avoid super wide brims or slouchy hats, but they can pull off any hat. You’ll look good in cowboy hats and fedoras alike, so take your pick!
For square faces, choose something a bit softer to help soften your features. A beret is perfect, but a baseball cap and the newsboy cap also look great.
Diamond faces are also very versatile and look great in brimmed hats or slouchy hats. Good choices include driver caps, cloche hats, and the traditional pork pie hat.
Oval faces look best in wide-brimmed hats and low crowns. This will help cut across your forehead and make your face appear less long. You can also pull off floppy hats!