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Look of the Week: Choosing a Hat for Your Personal Style

I’ve worn hats with confidence for years. They’re great for sun protection and to add attitude to an outfit. Many of you have asked me to write a post on how to choose a hat. I’ve heard that you’d like to wear them, but don’t know where to start!


Choosing your best hat involves your face shape, lifestyle and personal style recipe.

A flattering hat helps balance your face shape. If your face is large, a small hat will look disproportionate. If your face is wide, a narrow hat will be unflattering. If your face is long a short crown will look stumpy. It’s all about balance and proportion.

navy felt fedora

If you have an angular face, curved hats are a nice contrast. Round faces are flattered by straight lines. You’re looking for a contrast to balance the eye.

These rules are not set in stone and you need to consider how a hat makes you feel! I have a square jaw but seldom wear rounded hats. The style is wrong for my taste so I generally prefer angular hats with a dipped brim.

Now on to your lifestyle and personal style.

What kind of activities are you wearing this hat for? How formal is your style? If you have a casual lifestyle, opt for hats in simple shapes and material. Many women admire and buy hats that are too dressy for their lifestyle, so never wear them. Unless it suits you, leave those hats at the store.A navy felt hat is perfect for the weather on Howe Sound, BC

Shopping tips:

Go into a hat shop or department store and experiment. Try on different sized and shaped brims. Place the hat straight on your head, so it’s level front and back. Use a hand mirror or 3 way to check your side and back view. How does it look with your hair?

I prefer hair back from my face or behind my ears when wearing a hat. A large clump of hair hanging in front of my ears makes my face look crowded.

Try fedoras, rounded crowns, straight and floppy brims. Stand back from a full-length mirror and check how the proportion looks. Note that dark colored hats cast a shadow on the face that can accentuate our under eye shadows, so check for that too!

After trying several on, use your instinct to rule out what feels goofy. Do you prefer flat brims or rolled? Do you like angular hats or floppy, soft ones? Trial and error, using your gut instinct will point you in the right direction. Your hat needs to feel like an extension of you!

Navy Felt fedora

Once you own a hat, the trick to wearing it is put on as you head out the door for the day and simply leave it on. Pretty soon you’ll forget you’re wearing it until someone compliments you on your hat!

One more thing, if you’re painfully shy, hats may not be for you. Women in hats get noticed and often complimented.

Do you wear hats?

Thanks for reading and have a great day!

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40 Comments

  1. Hi Jennifer, Love your post on hats, such great information!! I was wondering what type of hat would you recommend for short hair with bangs and a round face? I am a 64 yo redhead with thinning hair and love to be outside gardening and walking our dog. Right now I am using a canvas bucket hat. Thanks so much!!!

    1. If you have a round face, a hat with a high crown and angular lines looks flattering. Fedora etc and ones with sloped brims

  2. Look for Wallaroo hats, made in Colorado, company owned and run by women. Great quality and many styles. All the hats have female names. Check out the Darby, she was my neighbor and CFO of the company.

    1. I will check them out!

  3. Haskell Sydney says:

    Thank you for resending your blog on hats and face shape. I love fedoras on you but not sure on me. My heart shaped face has slid to a more oval with age, 78. I live in rural Colorado so no place to try on hat’s except Walmart! I buy everything online and a hat would be very difficult. I have a small head and wind is a real factor this year out here. A chin strap with a fedora sounds silly. The only hats out here are cowboy hats and baseball caps. Neither work with my now short hair. So still wearing my ugly gardening hat when out in my yard.

    1. Leigh Kahn says:

      I’m also in Colorado. Many of the mountain towns have some great hat stores. Take a drive and visit one if time and budget allow! It’s fun to take a friend, have lunch and try on both silly and serious hat options. There used to be a great one in Breckenridge – I imagine it’s still there. Also there is a hat maker in Mancos. I’m guessing that’s mostly expensive, heavier hats for men, but I’ve been in several shops in smaller towns that feature all kinds of hats. Good luck!!