How to Choose Hats for Your Face Shape

Co-authored by Sarah McDonald

Last Updated: November 29, 2024 References

Most of you may have had trouble buying a hat: The hat looks absolutely incredible and super chic on the mannequin, and you realize painfully later that the hat worn around your head looks infinitely unsatisfactory. Then you are stuck in the vicious cycle wherein every hat seems odd or silly on you. You have become hat-paranoid. It's time to turn over a new leaf and resume the adventure. By picking a flattering hat based on your face shape, you can add flair and sharpness to your appearance.

Things You Should Know

Try a variety of hats if you have an oval or triangle face shape. Most hats flatter these faces, so it comes down to personal preference and style.
Go with an asymmetrical style, like a fedora or baseball cap, to balance a round face. For a heart-shaped face, try a fedora, cloche, or beanie.
Soften the edges of a square face by wearing a hat with a rounded brim. Sunhats, cowboy hats, and cloches are great options.
For an oblong face, try a hat with a flared brim and low crown, such as a sunhat, a cloche, or a large-brimmed fedora.

Part 1

Part 1 of 3:

Determining Your Face Shape

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Examine your face shape. You can have an "oval", "round", "oblong", "heart-shaped", "square", or "triangle" face. Read on to learn which type of face you have, and which hat would work best for its shape.
An oval face will have a length that is roughly one and a half times greater than your face width. The forehead is a bit larger than the jawline, and the angle of the jaw is a bit more round. An oval face will look like an egg.^{[1]
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Look for a “round face.” A round face will be the same width and length. A round face has a round chin, full cheeks, and around the hairline. It makes you look younger than other shapes.^{[2]
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An oblong face will be longer than it is wide. The forehead, cheekbones, and jawline of an oblong face will be similar in size. Oblong faces may feature high foreheads.^{[3]
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This face shape is very common. In a heart-shaped face, the chin is the narrowest part. A heart-shaped face has a broad forehead and/or wide cheekbones, and pointy chin.
A square-shaped face has a length almost equal to its width. The distance from forehead to chin and from cheek to cheek are roughly the same.^{[4]
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Triangular faces will be characterized by a large jawline, slightly smaller cheekbones, and the smallest forehead. A triangle face may be any length. Triangle-shaped faces are also known as pear-shaped faces.^{[5]
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Part 2

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Measuring Your Face

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Using a tape measure, measure across your forehead. Measure from the peak of one eyebrow arch to the arch-peak of the opposite eyebrow. Write down that number.^{[6]
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Using a tape measure, measure the distance across your upper cheeks. Start and end at the bump below the outside corner of each eye. Write down that number.^{[7]
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Using a tape measure, measure from the bottom tip of your chin to the bottom of your ears. Stop at the place where your jaw angles upward. Multiply that number by two. Write down that number. This is your “jawline.”^{[8]
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Using a tape measure, measure from the center of your forehead (at your hairline) to the bottom tip of your chin. Write down that number.^{[9]
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5
Ask yourself three questions. Using these measurements as a guide, ask yourself the following:^{[10]
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- What is the widest part of my face?
- What is the shape of my jaw?
- How long is my face? Is it longer than it is wide, and if so, by how much?

Part 3

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Selecting a Hat for Your Face Shape

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1
Choose hats for an “oval face.” Feel free to try all kinds of hats! You are blessed with a very versatile look! Pick up whatever suits your mood, as long as the hat is in harmony with your outfit. Women with oval faces can top off any hat.
- The possibilities are limitless! It only depends on your personal preferences.
- Experiment with earrings, necklaces, and bracelets.
2
Choose hats for a “round face.” Add some asymmetry to your look. You can perfectly handle a fedora, a newsboy hat, or a baseball cap. This symmetrical face cries out for a new angle: asymmetry. The roundness requires a slimming treatment.^{[11]
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- Steer clear of round crowns, which can emphasize the roundness of your face.
- It is wise to select a hat with a high crown and straight brim to give your face more angles.
- Your main goal is to choose a hat that helps distract people's attention from your facial curves.
- Slanting your hat forward draws out your face and gives a touch of definition.
3
Choose hats for an “oblong face.” Try a hat with a flared brim and low crown, such as a sunhat, a cloche, or a fedora with a large brim. The large brim of a sunhat may well offset the length of a long face.
- Avoid any hats with tall crowns, which only elongate your face even more.
- A cloche worn low to your eyebrows can help conceal your high forehead, and, like sorcery, create an impression of the shortened face.
- The large brim of the fedora also counterbalances vertical curves.
4
Choose hats for a “heart-shaped face.” Go with a medium brimmed hat, such as a fedora with a medium-sized brim, a boater, a cloche, a homburg, a beanie, or a beret. These are all good choices! These hats balance out the width of your forehead.
- Slanting the hat to one side will slim your face and draw attention to the eyes.
- Actually, any type will work well on you except those with large brims.
- Avoid shapes that accentuate the shape. Stay away from wide brims that only accentuate your forehead and narrow your chin.
5
Choose hats for a “square face.” Experiment with circular styles. Your defined and symmetrical face requires circular features to soften the edges of the face. Round crown and brim will do the trick, smoothing a boxy face and inducing the illusion of height and roundness.^{[12]
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- Opt for a sunhat, a cowboy hat, a homburg, a cloche, or a toque, which gives you a feminine and flirty touch.
- A beret will elongate and cushion your facial contour.
- Tilting the hat off to one side breaks up the symmetry pattern of your square face.
- A sunhat with a pair of sunglasses and a flowing maxi dress adds boho-chic to your ensemble. It is a perfect combination for your beach vacation.
- Don't wear a hat with a short brim, no brim, or a square hat. These two types of hats will both emphasize your angular face shape.
6
Choose hats for a “triangle face.” Feel free to try many hats. A triangle face is like an oval face shape that the options are virtually endless when it comes to a hat. Make sure your hat brings balance to your shoulder line, and accent to your garment.
- Never gets close to a crown that is narrower than the cheekbones.

Community Q&A

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I'm meeting a personnel manager for the first time for coffee, should I leave my fedora on or off?

Community Answer

A gentleman always takes his hat off when he steps inside. A lady usually leaves her hat on as it is part of her outfit.

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When in a first business meeting, should I keep my fedora on or take it off?

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Depending on cultural customs, the hat can be kept on when greeting other meeting participants, if the greeting is done with a handshake manner. Recommendations in the 'gold-period' of hat wearing was removing the hat in a nonchalant manner before shaking hands with someone, preferably so that the person in question does see the hat removal. This signaled dignified respect without theatrical showmanship.

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What hats are good for short hair and glasses?

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I would suggest a fedora, or beanie. However, a wide-brimmed sunhat might work as well.

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