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

I’ve worn hats withĀ 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 aĀ 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 yourĀ 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,Ā 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!

36 Comments

  1. 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 hatā€™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:

      Iā€™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! Itā€™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 itā€™s still there. Also there is a hat maker in Mancos. Iā€™m guessing thatā€™s mostly expensive, heavier hats for men, but Iā€™ve been in several shops in smaller towns that feature all kinds of hats. Good luck!!

  2. Yes, I wear hats a lot. I love hats. I wear them for practical reasons as well as a fashion statement. In the winter hats are a must to keep warm and in summer to keep the sun off my face and eyes. Almost no one I know will wear a hat. And they do always say they do not have the face for hats. You are right, they just are not choosing the right hat for their face and personal style.

  3. I needed this information today! A growth was cut off my head last week and the biopsy revealed an aggressive form of actinic keratosis that leads to skin cancer. I’ll be buying and wearing hats for the rest of my life. Thanks!

    1. I’m so glad you caught it at this stage Elaine! A string sunscreen and hats are your best defense. There’s some great hats out there.

  4. I’m the none hat wearing member of our team and had the most fabulous day trying some on and was really won over. We did a couple of blog posts on it and really appreciated the expert advise we received.

  5. I’ve always loved hats and wear them often. My hair is a bit too short for some, right now, but I let it grow longer in winter and wear a variety of different hats. You look great in all styles.
    b

  6. My favorite hat is the classic beret. In red. It looks great against the black hair that I still have–plus hats hide my bald spots!

    I wish we were in the era of women wearing hats all the time! I loved t(hat)!!

  7. Hi Jennifer, Great post about hats. I have a beautiful Helen Kaminski hat that I bought years ago. I wore it one time when I was traveling and had to dress up for my flight. I have never had so much attention from men! One nice man just told me up front that I looked fabulous. I was much younger then, of course. Great fun and the right hat can do that for you. Thanks for your lovely blog.

    1. Your hat sounds fabulous! I hope you continue to wear it these days šŸ™‚

  8. Such a nice post – the scenery looks so similar to New Zealand that it made me feel quite homesick (coming from NZ but living in Switzerland.

    xxYvonne
    http://www.funkyforty.com

  9. Love wearing hats but find I only wear cute winter ones. And I am never sure if I should take it off when I sit down at a restaurant or leave it as part of the outfit…

  10. I wear a red cowboy hat with a rhinestone tiara on it for every Arkansas Razorback tailgate, and now people call me “the hat lady!” The tiara has a big hog on it, quite stylish at a football game. One little girl asked me years ago, “Were you Miss Arkansas?” I winked at her mother, and calmly said, “Yes I was…”. Hats do get you attention!!!

  11. My closet is full of hats that I wear out of necessity but feel they don’t really flatter me. I’m too short for them, yet need a wide brim. Years ago I had a pre-cancerous growth removed from my scalp. My mother had a problem on her face. I’m really afraid of the sun now.

    Thanks for your hints on styles. Hair behind the ears, I’ll try that one.

    That white sweater is so flattering.

    1. I break the rule about brim size and my height all the time. Perhaps you could try a brim that dips. It would add movement to a large brim. You’re so smart to protect your skin! Too many women don’t.

  12. Martha Edmundson says:

    I love the hats you wear in your blog photographs. You are well on your way to convincing me to give them a try. I have a hat a bought on a whim at Nordstrom. It is a cowboy style in straw. For some reason, I put it on and take it right off again. Perhaps it is the face shape problem. I’ll take another look. Thanks for your insight.

    1. It could be the shape. I can’t wear cowboy hats or caps. I look simply dumb in them. Try on other shapes too!

    1. Wouldn’t that be fun?!

  13. Great tips!! I have a nylon hat by Sun Day Afternoons. It has a 3 3/4″ brim all the way around. I love how it looks and I get good coverage. If I’m wearing it while hanging out the wash or gardening, I wear a bandana underneath – it helps to keep me cool…plus since my hair is already ruined by the hat, I’ll continue wearing the bandana once I go back inside the house. If my hair is crazy in the morning, I’ll wear a bandana then, too. I don’t like to take my daily shower until I’ve done my gardening, house work, and exercise.

    1. Good coverage is so important! The bandana idea is brilliant. Hat hair bothers most of us. Thanks for sharing!

  14. You look fab in that lid J and I love women in hats!

  15. I left a HAT yesterday……..as it called MY NAME with OLD world straw, big brim flouncy flowers off to the side.IT was EXQUISITE.
    For a mere $865.00.
    I would need my own boat in the SOUTH of FRANCE and a HOT ITALIAN at my side………..
    Only missing THE BOAT these days!!!!!!

    XX

    1. That must have been some hat!! I hope you took a picture of it to share!

  16. i really enjoyed this post! my hair is very thin and straight and i’ve tried to embrace hats this summer in order to cope with the heat and humidity. thanks for the guidelines you offered to help with choosing the right hat.

    along the same lines, can you update us on your experience with rogaine? i am thinking of trying it and would love to hear how you are doing now that you are a few months into the process.

    1. Try some lightweight cotton and straw for summer too, Susan. You’ll find a shape you love and it’ll be easy to wear.
      The Rogaine is a massive success! I have regrowth all over the top of my head. I’m not planning to stop it anytime soon šŸ™‚

  17. Joanne Long says:

    That is a very flattering hat. You are right about attention. Women who wear hats do get noticed. They seem to draw the eyes to the face in a becoming way. Were your photos taken in B.C.? It looks like our coast.

    1. Yes they were. My husband took them this week in Squamish. It’s such a stunning place!!

  18. Thank you and what a coincidence your post is for me! My brother-in-law gave a fedora to me just this past weekend because when I tried his on the whole family loved it on me.
    I thought I was too old (61) to wear it but I also thought of you and how your polished style incorporates hats seamlessly. I love it! I will wear it proudly! Can I say it is made by Goorin Brothers, NYC, and is beautifully handmade of nylon, can be rolled up for travel and pops up again in beautiful shape? It is from the “fedora” line but they have many styles. I am merely a consumer, not paid to enter this on a blog.
    BTW, coincidence you are a knitter, I am too. Are you on Ravelry?

    1. I too, love Fedoras! They’re a snappy shape. I have a black straw one from Goorin Brothers that I bought on a trip to visit my daughter in Vancouver. I yum 60 in a few weeks and think I wear more hats now than I did in my 40’s!

  19. Thanks for this article Jennifer – I always admire the hats you wear in your photos. After realising that my thinning hair was starting to get quite sparse on top I’ve recently purchased several hats but haven’t yet been able to work up the courage to wear them. Silly thing is that I love them on other people. I’m normally fairly outgoing but I think I’m worried that people will wonder why this middle-aged woman is wearing a hat or think they look silly. My daughter helped select them so I know they don’t. I guess I just need to “bite the bullet” and go shopping with her wearing one. Wish me luck!

    1. Go for it Vickie!! If your daughter helped you pick it out, I suspect it looks great on you. Take every opportunity to try on new shapes and colors. You’ll get hooked. The bullet is a dose of attitude that other accessories just can’t match. Please let me know how it goes. Email me a photo!!

  20. I have a large collection of hats, but which one I wear on a particular day has more to do with what I’m wearing and above all the level of windiness. Certain hats stay on better. One with a huge brim and a tie under the chin is good for the beach (windiest spot of all). A cloche also is good on windy days.

    1. Windiness is a big consideration! Even with a chin strap, a very wide brimmed hat is harder to wear on a windy day than a smaller one!

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