How To Choose the Best Hat or Headpiece for Your Face Shape
Style Guide

How To Choose the Best Hat or Headpiece for Your Face Shape

blog
22 / May / 2025
5 min read

Hats and headpieces are our favourite accessories to top off a look with (pun intended). If you’re trying to add them to your style roster too, there’s one thing you must know: You have to consider your face shape before you choose headwear.

There are no hard rules in fashion, of course! Wear whatever you feel is best for you. What we do want to offer is a little bit of guidance so you can rock a piece of headwear that complements your features and style perfectly.

How do I know what face shape I have?

There are the most common face shapes: oval, square, round, heart, and diamond. Here are some distinct features of each shape:

Oval 

Oval faces are shaped exactly like an oval. The forehead’s width is a little bit wider than the chin. They also have high cheekbones.

Square

A square face has an angular jawline. The forehead and the jaw also have, more or less, the same width. The tell-tale sign is the angular feel of the facial contours.

Round

Similar to the square face, a round face’s forehead and jaw also have the same width. The main difference is a round face’s contours are softer and the cheeks are usually full.

Heart

This one’s really like a heart! The forehead is wider than the chin, and the chin is a bit pointed (which makes it different from the oval shape). 

Diamond

Think oval but more angular! The jaws are narrower than the forehead, but the cheekbones are defined. 

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How to measure your face to find your shape

If you’re still unsure of which shape you have, the best way to determine it is by measuring different parts of your face.

You’ll need a measuring tape and a notepad to jot on your measurements.

Start with your face length. This is from top to bottom of your face. So measure from your hairline to the lowest part of your chin.

Next, find out your forehead width. Measure the distance across your forehead from hairline to hairline, but make sure you don’t curve the measuring tape and keep it flat.

Then, check your cheekbone width. For this, you’re gonna need to find the highest point of your cheekbone, and measure from one high point to the other (yes, left and right).

Lastly, determine your jawline width. Place the measuring tape below your ear until the centre of your chin. Multiply the number you get by two.

Based on the numbers you get, you’ll have a pretty good idea of whether your forehead is wider than your jawline or if they’re the same and so on.

There are some cases where a person may have a combination of face shapes. We think that’s like having the best of both worlds! You can rock more styles.

Now that you know what your face shape is, it’s time to get the right hat or headpiece.

Hats for different face shapes

Best hats for an oval face

best hat for square face

Great news for you: most, if not all, hat styles work for your face shape! Take this opportunity to explore as many options as possible. There are so many to choose from, depending on your personal style — whether it’s a classic fedora or a baseball cap. The style sky’s your limit.

Best hats for a square face

best hat for square face

The key is finding contrast for balance. Complement the angular contours of your face with rounded or curved edges. Wide-brimmed hats are a great choice! Bucket hats, panama hats and other hats with a round brim are all good options too.

Best hats for a round face

best hat for round face

Like the square face, a round face will benefit from a little bit of contrast. Complement your angular yet soft features with clean lines and a bit of structure. This goes for wide-brimmed hats and bucket hats alike.

Best hats for a heart face

best hat for heart face

Medium brim is the way to go for heart-shaped faces! These balance out your prominent facial features. The goal is to complement them — not hide them. Think: newsboy cap, boater, cloche, fedora and beret.

Best hats for a diamond face

best hat for diamond face

Like heart-shaped faces, diamond-shaped faces are complemented well by medium-brimmed hats. The key is in choosing something that has a bit more width to go with your prominent cheekbones. A panama hat, newsboy cap or medium-brimmed fedora will work great for you.  

Headpieces and headbands for different face shapes

Best headpieces and headbands for an oval face

best headpiece for oval face

You won the headwear lotto, oval face! Like hats, headpieces and headband options are aplenty for you. From tiaras to halos, the choices are abundant. So it really boils down to your style. 

Best headpieces and headbands for a square face

best headpiece for square face

Soften your angular features with pieces that offer a touch of roundness. Think padded headbands, floral embellishments, and pearl headpieces.

Best headpieces and headbands for a round face

best headpiece for round face

This time, we do the opposite of what we want for square-shaped faces. Try more angular or edgy pieces such as hair vines or headpieces with angular designs.

Best headpieces and headbands for a heart face

best headpiece heart face

Try to go for headpieces and headbands that complement your features, such as side combs, clips, and lower-set headbands. These balance broad foreheads and add width to the lower part of the face.

Best headpieces and headbands for a diamond face

best headpiece for diamond face

Similar to heart-shaped faces, you’ll benefit from pieces that enhance the brow and chin. Think fascinators and embellished headbands.

Now go ahead and rock that hat or headpiece!

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