Best Stylish Sun Protective Hats for Women Over 50

Kim and I originally covered this topic back in 2021 (note our younger selves in the pic). When it comes to staying stylish under the sun, protecting your skin is just as important as looking your best — especially after 50. The right hat can be your best friend, offering much-needed shade while adding a finishing touch to your outfit. From classic fedoras to baseball caps, there’s a hat for every face shape, style, and activity.It is no mystery that I love a great hat, winter, summer or fall. In this post, I’m sharing the best stylish sun protective hats for women over 50.

cindy hattersley and kim wheeler

Kim and I in 2021. Doesn’t Kim look like she could be my daughter? She does not age!  I am wearing a wallaroo hat,that I still enjoy.white linen tunic from Eileen Fisher, similar mules from Etsty here, bracelets, and earrings also from Etsy. If you like this look I would replace the dated leggings with these kick flare linen pants from Banana Republic ( I own them in brown and am thinking of purchasing the black).

Best Stylish Sun Protective Hats for Women Over 50

Choose the Proper Hat for your Face Shape

Be sure to choose styles that complement your features by contrasting, or balancing them. Hats.com has a great face shape guide here.

Frank and Eileen Tuscany Set with Janessa Leone Bag & Brixton hat

The Brixton Proper hat is another favorite. Here I am styling it with the Tuscany Getaway set from Frank and Eileen, comfy sandals similar here, belt here, and my Janessa Leone backpack.

Wide Brim Hats are the Ultimate Sun Blockers

The classic fedora, rancher or boater could be included in this category. They have the ability to provide the maximum coverage for your face neck and shoulders. There are many hat companies that specialize in upf sun protection as well, such as SolbariWallaroo hats, and Coolibar.

cindy hattersley wearing nicole-paloma,-linen-wrap,-helen-kaminski hat

This wide brim  hat from Helen Kaminski is the ultimate sun protector. I think it looks best with something full on the bottom like these wide leg pants or a full maxi skirt or dress. I am wearing Merseas fabulous linen wrap,  similar sandals here,  or here. I love this hat (it is packable) but I don’t wear it as often as some of my other favorites because it is large and more dramatic. The earrings are from Amazon here.

BR Shirt Dress with Janessa Leone hat & bag

Janessa Leone recently let me pick a hat from their new collection and I chose this hat. It is supposed to be packable. It is very lightweight, has venting which is great on a hot day,  It is all white but I added a bandana, to complimennt this popular shirtdress from Banana Republic, my fitflop thongs,  and my Janessa Leone bag that will also hold this hat on the front in between the straps. Hat Attack also has a more reasonable version here.

Packable and Foldable Styles for Travel

My favorite  women’s sun hats are packable and foldable for obvious reasons.

janessa leone buket hat & bag all black outfit

This Janessa Leone Felix Bucket hat is a longtime favorite of mine. It is pricey but I have dragged it on multiple trips and it retains its shape every time. I am wearing it with my Eileen Fisher linen pants, dolce vita slides, similar here, cynthia ashby tee, and Janessa Leone bag.

White Shirt Linen Pants & Helen Kaminski hat

This Helen Kaminski Provence 8 hat I have owned for several years. It is another hat that I wear often. It is lightweight, packable,  and it always retains its shape. The linen pants are from Bryn Walker here, the linen shirt from Eileen Fisher, and the laidback london sandals similar here.

Sport Caps

I know many of you are not fans, but I love a good baseball cap, but I love them. They are great for a bad hair day or for riding in your husband’s car with the top down. You need to slather on extra sunscreen ( don’t forget your ears), because they don’t cover the  sides of your face.

cindy hattersley at the Farmers Market with Janessa Leone bag

This Wyeth rattan baseball cap is a go to for me during the summer. It is breathable and cool.I am wearing it with my favorite Bryn Walker linen pants, Michael Stars tee, and my Janessa Leone bag.

Shop Stylish Summer Hats for Every Budget

Shop Ebay, Poshmark and other resale outfits for designer hats (just pay attention to their condition). I have purchased several Helen Kaminski and Janessa Leone hats there.  Nordstrom Rack has several Helen Kaminski hats at great prices here. I find Hats.com to have the best all around prices on straw hats, unless they are on sale elsewhere.

You might also enjoy my post Stylish Summer Hats that will Help you Beat the Heat in Style.

Don’t fret if your raffia or straw hat becomes misshapen. Raffia hats are particularly easy to reshape. I reshape mine after nearly every trip with my steamer or iron. Eric Javitz has a great article on how to reshape your hat here. My personal advice is to invest in a couple of hats from the best hat manufacturers , consider cost per wear (cpw), but there are many offerings available at great prices, and some are quite good (read the reviews, and note what they look like on the models).

A stylish hat is much more than just a way to keep cool — it’s a reflection of your style,  and confidence. This summer, embrace the Best Stylish Sun Protective Hats for Women Over 50, and let your hat be the finishing touch that brings your summer looks together with ease. Stay stylish, stay sheltered, and enjoy everything the sunny months have to offer! Now let’s pop over and visit Kim for her stylish choices!

NORTHERN CALIFORNIA STYLE

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18 Comments

  1. Cindy, both you and Kim ALWAYS look beautiful and stylish!
    I love a baseball hat for walks and trips to the gym and a straw hat for outings. Wide brim to keep the sun off my face.
    Have a wonderful week!

  2. You look so cute, and tomboyish in that Helen Kaminski Provence 8!
    How fun to have such a great collection of hats. Not only do the provide great sun protection, but they add such personality to an outfit. I think we could all benefit from adding a little out of the ordinary touch to our everyday. A hat, a scarf, a special piece of jewelry…
    By the way, last year I went out of my way to try some Bryn Walker linen pants. They are wonderful! I got a pair of white, wide legged ones. I love the fit, and the quality. The shape of the legs is extra feminine and flattering. Thanks for the recommendation!

  3. Cindy, I am with Joanne and Martha with hats-small head and shorter hair. I’ve yet to find one that looks relatively good on me. The problem with short hair and a hat, it all looks so flat after. Love the hats on you and of course, your style. Ball caps do work but usually only for a bad hair day. Maybe I just need to spend some time on trying to find one….

  4. I have a long J Crew gingham tunic top exactly like your long white one from EF and I tried to wear it with white cotton capri leggings that have eyelet around the hems. It’s the most adorable combination -when you’re standing still- when I walk, the top crawls up and wraps around my legs. I don’t understand clothes sometimes, this is a problem often with leggings. I won’t be caught dead in pleather leggings so I don’t know what to do. You look great in this, however, it’s my favorite.

  5. Can I make you my personal shopper, Cindy??? I love popping in here—and that we have a similar style. Seriously, I am sure I have mentioned it before but if ever there were a way to make that a business—long distance. Let me know! :))

    1. Hi Jeanne

      I know we have a similar style. I feel like I should be asking you for advice!

  6. Cindy, you have the best collection of hats. As for baseball caps, I love them but they don’t suit my face … not that I let it stop me. That rattan cap is fantastic. You look amazing in the wide brim … with those fabulous wide leg linen pants. I have them in my cart as well as the packable JL bucket hat. Great round up. Looks like it’s going to warm up here today and I’ve got my hat ready! xo

  7. Cindy, I just wanted you to know that I was delighted to open my email a few weeks ago and discover that your blog had returned. Thank you for changing your provider to include Comcast. I appreciate your excellent information and positive outlook!

  8. I wear hats all the time when walking or spending time outdoors. I wish more had a tie or way to secure them so they don’t blow off in the wind.

  9. I used to wear baseball caps thinking the long brim was giving protection, until I got a sunspot on the side of my face. My dermatologist pointed out the fact that the side of my face and ears were getting no protection (as you pointed out too) so I changed to sun hats.
    Having a small head presents a problem though. Many are too big on me. I wish they all offered an adjustment on the brim.
    You wear hats so well, Cindy!

    1. Same here with a small head – and short hair! Hats and short hair are difficult I think. I also love them, live in Georgia with heat and sun, and should wear them regularly.

  10. I love a good sun hat. But I really don’t love what my hair looks like when I take it off. I have fine curly hair and hats just do a number on it. Any suggestions ? You and Kim have lovely silky long hair which seems to go well with your incredible hat style.

  11. I just ordered the cap from San Diego Hat! Love it.
    I don’t end up wearing hats that much when I am dressed up, not sure why? Maybe because it is so hot and humid here in the summer and I cannot take the hat off once it’s on? Not sure.
    I do think they are great to protect your face and your hair (especially white hair!) from the summer sun.
    I take them on all vacations. If they don’t pack well, I carry them on with my magnetic hat clip!

  12. Cindy love that you have such a beautiful hat wardrobe! You inspire me to wear more and just around as I run errands and things…
    Great looks with these cute outfits!
    You look amazing in hats. I need to add a new one this year… Some of mine are getting old. I loved this day we met up. Wish I could meet you and the ladies again at Wisteria! I should have gotten that hat.
    xo

  13. Such a great post. I love baseball caps and wear them out walking…but you are right about needing the extra sunscreen!

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