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How to Wear a Hat this Summer

June 4, 2019

Did you know that wearing a hat is a great way to elevate a simple look to wowsa? Yep. That’s what “they” say! But it turns out there’s a right way to wear a hat so it accentuates your look rather than detracts from it. Plus, we gals just need to know what to do with the hair!! Amiright? I’m no expert, but I’ve done my research so you’ll know how to wear a hat this summer.

Do you wear hats during the summer? Of course, it’s actually fashionable and smart to wear hats throughout the year. But today let’s focus on the types of hats we’re more prone to wear during summer.

Wear a Baseball Cap

How to Wear a Baseball Cap this Summer
everyday yoga skort in medallion print (wearing small) // cinched hem henley tee in bougainvillea pink (wearing small) // palm necklace // baseball cap in navy // ECCO leather sandals // nylon tote bag // sunglasses // star & moon earrings // small gold hoops – See More of this Look Here.

I’ve never really thought I looked as cute as other gals in baseball caps, but I think they just take some getting used to. You have to accept that you’re not going to look the same as you do with your hair down and no cap. Duh.

Hat Styling Tip #1 – Just do it! And do it and do it. Get used to seeing yourself in a cap or hat. Give it time. Soon you’ll be okay with what you see in the mirror and eventually you’ll love it!

How to Wear a Baseball Cap this Summer
baseball cap

Hat Styling Tip #2 – If you have longer hair, you can pull it up in a low messy ponytail or bun. Then pull it through the opening in the back of the cap or wear it below the cap. Keep the ponytail or bun messy and fun!

Wear a Wide-Brimmed Straw Hat

How to Wear a Hat this Summer
Columbia sun hat

You’ve probably heard you need to wear a wide-brimmed hat to protect yourself from the sun. And indeed, a hat is a great sunblock. But keep your height and size in mind when selecting your wide-brimmed hat. Like your other accessories, such as your handbag, proportions matter.

Hat Style Tip #3 – Tall and larger framed gals will look more in proportion with very wide-brimmed hats, but if you are more petite select a hat with a brim that stays within the width of your shoulders.

How to Wear a Hat this Summer
Similar sun hat

But definitely carry a packable hat with you on vacation to the beach or anywhere you may be in the sun a lot. Select a hat that you can roll or fold up in your suitcase. The one I’m wearing in the photo above flew with me to Oregon with no problems.

Hat Style Tip #4 – Choose a flexible hat that you can pack in your suitcase for vacation.

How to Wear a Hat this Summer
tie dye dress (wearing small) // sandals // necklace // bracelet // sunglasses // moon & star earrings// hoop earrings (similar) // hat (similar) – See More of This Look Here.

Hat Style Tip #5 – If you are tall you can wear hats of contrasting colors more easily. But if you are petite, wear a hat that is similar in color to your outfit or that is close to your skin tone to gain a few inches.

How to Wear a Hat this Summer

Also keep in mind your face shape when selecting a hat.

Hat Style Tip #6 – If you have a long face, choose a hat with a shorter crown and a medium sized brim so you want look even longer. Conversely, if you have a small face or delicate features, select a hat with a small brim.

Hat Style Tip #7 – If you have a round face, choose a hat with an angular crown, like the one in the photo just above. If you have an angular face or square jawline, you will look prettier in a hat with a rounded crown.

Seersucker Fit & Flare Dress
seersucker fit & flare dress (wearing an 8, TTS) // ankle strap sandals // gold bangle (similar) // beaded sphere earrings // star necklace // wicker and leather shoulder bag // hat (similar) // sunglasses – More on This Look Here.

Don’t be afraid to wear your hair down under your hat, too. We often worry about “hat hair.” But really, we rarely get that maddening indention with a well-fitted hat. As long as it’s not tight on your head, you probably have nothing to worry about. Or just keep a comb and travel size bottle of hairspray in your handbag so you can “poof” a little after removing your hat.

Hat Style Tip #8 – Wear a hat with a pared down outfit. Don’t wear a hat with a complicated or “fussy” outfit. It will only add to the mayhem! In the photo above I’m wearing a hat with a simple seersucker dress. You can see more of the look here.

Wear a Hat Hiking

I almost always wear a wide-brimmed, moisture wicking hat when I’m hiking or spending time on the beach.

Columbia shirt // Columbia hat

Choose a hat that offers sun protection as well as moisture protection. I like a lightweight, polyester hat rather than one made of cotton. And definitely look for one with a chin strap. You can wear it when the wind is blowing, and tuck it in the cap when you don’t need it.

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Do you have tips?

Like I said, I’m no expert on wearing hats. There are many women who pull off this chic accessory and sun damage protector better than I do. If you have tips for how to select and wear hats, I welcome your input in the comments. Thanks so much for reading and sharing.

Today’s Challenge:

Today’s challenge in the Dressed for My Day Challenge is to “think about someone you know personally whose style you admire. Interview her in some way, asking her how she puts her outfits together, where she shops, what her style philosophy is. She’ll feel flattered and share gladly.”

I’d love for you to tell us about what you learned in the comments below or on the Facebook group page. In Instagram you might tag a photo of her with the hashtag #dressedformydaychallenge.

Don’t Miss a Post:

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Blessed for My Day

Sometimes I forget that everything I have isn’t really mine at all. It’s His. Each gift God has blessed me with is really a trust, a stewardship. I’m given the privilege of enjoying my family, my home, my career, my possessions, but I’m also responsible for taking care of them, holding them in open hands and even sharing them with others.

Do you need to be reminded today that someone you’re clinging to is not yours at all? Or maybe you need to remember that what you’ve worked so hard for is also a trust? Honestly, when we hold our blessings in open hands, we find that we can trust God and do not need to fear. We are relieved of much anxiety and greed.

Yours, Lord, is the greatness and the power and the glory and the majesty and the splendor, for everything in heaven and earth is yours. Yours, Lord, is the kingdom; you are exalted as head over all. ~ 1 Chronicles 29:11

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xoxo, Kay
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37 thoughts on “How to Wear a Hat this Summer

  1. Thank you Kay for the excellent hat wearing tips. You look great in all of them. I am definitely a hat wearing Southern Gal. I have been wearing hats for probably close to 20 years….who knows, maybe longer. I am not even sure how many hats I have because I have donated a few over the years… least 100. I know that sounds absurd. This includes church hats, summer hats, winter hats, winter toboggans, casual hats, and numerous ball caps. I have been known for wearing hats so your post today caught my attention right away. Also, as always your BFMD touched my ❤️. ~Lisa~

    1. That is super, Lisa. I hope your sharing encourages the rest of us. I generally fail to remember to add a hat. But I’m trying to do better with that because I believe it really does elevate a look. And I think the biggest key is just getting used to it. Blessings! ?

  2. Thanks for the tips! I have very pale skin and really thin hair so I try to always wear a hat…especially in the summer. Finding one that I feel looks good is such a problem. I will definitely heed your advice. Thanks!

    1. Yeah, I just learned those tips and they really make sense to me. I’d heard the same advice about body proportions in regards to belts and handbags and jewelry, but hadn’t considered that it would of course apply to hats as well. Makes sense. Good for you, wearing hats for sun protection. Smart!! ?

  3. I have short hair, and I think I don’t look good in hats (although I love them.) In addition I have a small head, so it is hard to find hats which fit me. I keep trying.

    1. Tip #1 ?. Just wear them. I generally feel awkward at first too. But I’ve thought about it. Have I ever really seen anyone else wearing a hat and thought to myself “she doesn’t look good in a hat?” No! I haven’t. We just talk to ourselves that way, but we don’t judge anyone else as harshly. That’s gotta stop. ?

  4. I love hats and enjoyed all your tips on wearing them. But…..I wear glasses and that always seems to throw off the look for me, especially with a ball cap. You had glasses on in one picture but we saw the back of you and not your face. An tips on wearing lasses with hats?

    1. Well keep in mind that most anytime I’m wearing a hat I’m also wearing sunglasses. So I have a feeling you don’t really look odd at all. I think we’re our own harshest critic. I suggest you follow tip #1! ?

  5. You look great in all these hats Kay. I have a small head so I’m a hard fit. If I need a baseball cap I often try on a child’s size cap, the fit is pretty good! Love the Blessed For My Day?

    1. You look adorable in all these hats!!! I’ve tried the baseball hats but it seems like with chin length hair, even then I have that tuff of hair that sticks out the hole in the back. Are visors still in…LOL That’s what I wear when I walk.

      1. Hahaha! I generally wear a visor when I walk too. And it’s definitely no fashion statement. Ha! But I think I probably should be wearing a baseball cap because it would protect my scalp from the sun. I’ve definitely switched to a cap for golf because of how long I’m in the sun then.

        1. Beverly I found a ball cap today like the one you have on where you can pull the back tab and then stick it into the hem of the cap after you make it tight..WIN ! Now..just to get over the thinking it doesn’t look good on me 😉 And…I don’t wear my visor often either because the top of my head burns otherwise so the cap will be more protection.

    2. Deb I will have to try your trick in trying on a child’s size hat as sometimes I can’t pull a cap tight enough to fit my head either.

  6. This is such a great post topic!!! Thanks for sharing all your research! Each of the hats suited you so well. The packable hats are my favorites. Just recently, I have noticed wide brim sun hats with one scalloped notch in the back to accommodate a low ponytail -genius for hotter, stickier days.

  7. Kay, I love your hats…especially the big brimmed! I have short hair and inevitably end up with hat hair or just BAD hair! However, I do always wear a wide brimmed hat at the beach to protect my face. I’ve tried growing out my hair but it makes me look old. ? I so wish I could be a long haired gal. You look great!

    1. Honestly, I’m a little envious of gals with short hair. And I probably will go short again eventually. But I don’t feel like I look as good with short hair as others do. I guess the grass always looks greener!! ☺️

  8. Great post! I wear hats occasionally but had no idea the do’s and dont’s! Thank you for your research!

    It is all His! May we steward well what we have been abundantly given! Blessings to you!

  9. Hats…I love how they look on others, on me, not so much. I’ve purchased quite a few over the years. They get worn once, maybe twice and then discarded. I did purchase another beach hat for this summer. I liked it in the store, we’ll see! What I really liked about it is the inside band is adjustable. That’ a big plus because they are usually to big on me and end up blowing down the beach.
    Baseball caps are ok. I wore one the last time my hubby and I went kayaking. It kept my hair from being blown in my face all day.

  10. I love the picture of you in the seersucker dress and sunglasses – the hat adds a touch of elegance to the whole look. I’ve always been told I have a good “hat face”, and I used to collect antique hats, but I almost never actually wear hats. Guess I need to change that!

    1. Hey, if you have a good “hat face” definitely use it to your advantage! ? I do think some gals look more “at home” in hats than others. ?

  11. Excellent post! The tips are really good. I totally agree about wearing a hat until you get used to it. I wear baseball caps all the time on weekends. The more I did, the more I got used to how I looked in them. Throw on a pair of great earrings and you’re set. One thing about wearing a hat–my hair is thinning, plus I color it. So wearing a hat saves wear and tear on my hair. (hey that rhymes!)

    1. Yes, I totally agree that wearing a hat helps protect our head and hair from the damage the sun can do. Great point. Thanks for chiming in!

  12. I too try to wear a hat when ever I am outside. I have had several cases of skin cancer and my dermatologist highly recommends it. I have found some hats even come with sunscreen. My favorite is a company called Coolibar. The only thing I would add to your wonderful post about hats is a chin strap for any activities that might pull hat off. I get annoyed if I have to keep my hand on my hat. And if I don’t need a chin strap I tuck it up in my head so it’s not in way.
    I loved your pictures showing angular hat versus rounded hat. I had to thought of that before.

    1. Kristin, where do you get the Coolibar hats? I’ve searched online and can’t find them anywhere. But I do find Coolibar shirts. I’d love to know where you buy them. Thanks for sharing!

      1. Kay, I shop directly from them.

        I have had good success with this company. I have used their swim cover ups, swim suits, and swim shirts. I love to be in the sun but I am trying to keep the cancer away!! Their clothes run generous.

  13. You look wonderful in all the hats Kay, and you’re right, it takes time to get used to them on ourselves. I’ve never been one to wear hats; but after seeing you, and reading your tips for the right hat, I may try them. So in meeting today’s challenge, I’ve not actually interviewed anyone about their fashion style, however, I do read several fashion blogs, and in so doing, I feel I’ve been stretched to try new things that are sometimes out of my comfort zone. I’m not one to wholeheartedly copycat; but I’ve learned valuable things from each Blogger which has helped me define my own personal style. And since my style is Classic, it’s been good for me to try new and fun ideas! Have a blessed day in the Lord!

    1. Great Nancy!! I love your teachable spirit. I think that’s something we all have to cultivate so we can stay relevant and contemporary. Thank you so much for sharing.

  14. You look great in the hats. I keep buying them and they sit in the closet. It I have always thought that I look best in a cowboy hat! Years ago, at my wedding, I had a cowboy-styled har with a veil. I appreciate the advice on the ball caps too…I need to wear them in my husband’s convertible, but I have never liked them on me!

  15. Thank you so much for pointing out that tall people can pull off a wider brimmed hat better because it makes them look more proportional. I have been trying to find great, fun baseball caps and other hats that I can wear around. I am starting to get sunspots, so I want to keep my face out of the sun as much as possible. It sounds like I will have to start looking for hats!