How to Find the Best Hat for Your Face Shape

Selecting a hat that will look flattering on you can seem like an intimidating process, especially when you're ordering a hat online. However, if you keep your face shape in mind during the selection process, you will be able to help determine which hats will look best on you without even having to try them on! Follow this handy guide to find the best hat for your face shape.


Find Your Face Shape

There are several ways to find out what type of face shape you have. One way is to take a photo of yourself and trace the outline of your face. The type of shape that you make will reveal what face shape type you have. You can also observe your shape by standing in front of a mirror with your hair pulled back and tracing the outline of your face with a tube of lipstick or a bar of soap.

Measuring your face from cheekbone to cheekbone, across the widest points of your jawline, across the widest points of your forehead and from the tip of your hairline to the bottom of your chin will give you several measurements to help determine your face shape. After recording your measurements, you can use our handy face shape chart to determine what shape your face most resembles. You can find this chart on our resources page under the title, How to Select a Flattering Hat.


Pick a Hat Type

Do you need a dressy hat for a special occasion? Are you looking for a casual hat to wear while running errands? Will you be wearing this hat outdoors? Knowing when and where you plan to wear your hat will help you determine the type of hat that you will want to choose. Each hat type is usually available in several styles, fabrics, or color choices, so that you can find one that suits your needs.

Our Hat Buying Guide has great information about different hat types and styles. While this is a wonderful resource for selecting hats for cancer patients, it also provides an overview of each type of hat, which can be helpful for anyone who wants to find a great hat- not just cancer patients! Once you familiarize yourself with the different hat types, you're ready to select one that will be the most flattering for you.

The following chart will help guide you through the selection process based on your face shape and hat type, as well as provide some suggestions of hats you might want to try:


Oval Shape

If your face is oval shaped, you will look great in just about any hat. With this face shape, versatility is key and the style you select will likely have many suitable options for you to choose from. You can have fun with different shapes and colors without having to worry about finding something that isn't going to be unflattering for your face shape.

Dressy Hats: Lacey Cloche Hat, Sheer Margaret Flower Hat, Vintage Angelica Two Tone Cloche Hat

Casual Hats: Versatility Newsboy, Cotton Roller Hats, Triumph Beret

Outdoor Hats: Brimmed Cotton Linen Bucket Hat, Maureen Sun Hat, Kendall Fedora Hat


Round Shape

If your face is round shaped, you will want to choose hats that feature angled brims to balance out the roundness of your face. Hats that add height will help to lengthen the face as well. Fedoras are often a great choice for this face shape. It is best to avoid floppy shapes like wide sun hats or berets.

Dressy Hats: Eva Cloche Hat, Lilian Upturn Hat

Casual Hats: All Cotton Helen Hat, Jayda Fedora Hat

Outdoor Hats: Mya Fedora Hat, Kendall Fedora Hat


Heart Shape

If your face is heart shaped, hats with a small to medium sized brim do not accentuate the wide forehead that most heart shaped faces feature. Asymmetrical styles like fedoras and cloche hats are typically great choices for heart shaped faces.

Dressy Hats: Felt Nina Hat, Eva Cloche Hat, Paisley Ribbon Cloche Hat

Casual Hats: April Cloche Hat, Cotton Flapper Hat, Tracie Newsboy Hat

Outdoor Hats: Metallic Nautical Cloche Hat, Samantha Shimmer Sun Hat, Mya Fedora Hat


Square Shape

People with square shaped faces want to choose hats with wide brims and a round crown to soften the jawline. It is best to avoid hats with angled brims because it accentuates the angled features of a square face and can make the face appear larger. Also, while wide brims are desirable for square shapes, it is best to avoid any sun hats or cloche hats with flat or angled tops.

Dressy Hats: Rowan Bow Hat, Sheer Margaret Flower Hat, Brimmed Hailey Hat

Casual Hats: Denim or Stone Bucket Hats, Pleated Newsboy Hat, Cotton Brandi Hat

Outdoor Hats: Wooden Bead Sun Hat, Deanna Color Block Sun Hat, Sherry Ribbon Braid Sun Hat


Diamond Shape

Diamond shapes look great in all shapes and sizes of hats. When selecting a style for a diamond shaped face, you can focus more on the fabric type or color you desire without worrying about finding a certain shape or size to give a flattering look. Have fun with design elements and fun shapes to play up the beautiful shape of your face.

Dressy Hats: Lacey Cloche Hat, Pinstripe Bow Cloche Hat, Jessie Velvet Bow Cloche

Casual Hats: Florette Newsboy Hat, Denim Bucket Hat, Braided Hazel Newsboy

Outdoor Hats: Robbie Sun Hat, Brimmed Natalie Hat, Knotted Cloche Kassie Hat


Rectangular Shape

For a rectangular shaped face, you want to select hats that are wide with short crowns. Wide flat brims or curled floppy brims will work best for this face shape because they help to add width to the face. Hats with longer or taller crowns should be avoided because they will further elongate the already long rectangular shaped of the face.

Dressy Hats: Brimmed Hailey Hat, Kristen Cloche Hat, Sheer Margaret Flower Hat

Casual Hats: Minnie Newsboy Hat, Linen Logan Hat, Softie Baseball Cap

Outdoor Hats: Colette Ribbon Hat, Maureen Sun Hat, Kristen Sun Hat


Pear Shape

If your face is pear shaped, hats with a full crown and a wide brim will help to balance out a wide jawline. Steer clear of cloche hats and fedoras that feature a tapered crown, as they can accentuate the jaw width that is usually associated with pear shaped faces.

Dressy Hats: Linen Poppy Hat, Jessie Velvet Bow Cloche, Rowan Bow Hat

Casual Hats: Joann Newsboy Hat, Sydney Newsboy Hat, Raelynn Newsboy Hat

Outdoor Hats: Brimmed Natalie Hat, Ribbon Braid Rachel Hat, Maureen Sun Hat



What hats look best on you? What are your best tips for selecting a flattering hat?