Wow. Look at that face. Makes you smile, right? There’s a good reason this ebullient woman is smiling so big.

It’s the hat. Obviously.

Almost everyone looks good in a hat, if it’s the right one, and there are lots of styles to fit lots of heads: the jaunty “Annie Hall” bowler in this painting; Indiana Jones’ I’m-Too-Sexy-for-my-Hat fedora; that eye-catching Chapeau du Matin that Audrey Hepburn flaunted in Breakfast at Tiffany’s. Not to mention berets, cloches, boaters, porkpies, turbans and fascinators.

My mom wore a pillbox hat to church every Sunday in the early 60’s, channeling her inner Jackie Kennedy.

I love hats. Yet, I rarely wear one. When I look at this painting – at how confident and joyful this woman looks – I wonder, why not? Do I think it’s just impractical or am I … chicken?

Audrey Hepburn wearing Chapeau du Matin in Breakfast at Tiffany's
Aside from the most obvious and practical reason to eschew hats – namely, hat hair – I think we have to be pretty comfortable in our own skin to wear hats in public these days. Hats haven’t been a ubiquitous fashion accessory for decades, unless you’re English royalty or at the Kentucky Derby. So, wearing a hat – other than a ball cap, which doesn’t count in my book – is an exercise in self-confidence. Indeed, be prepared to stand out in a crowd.

Thing is, while you might be thinking others are looking at your fashionable hat and saying to themselves, “how silly”, they’re most likely simply registering something different or unique in the usual scenery. For most of them, the fact that you are wearing a hat zips in and out of their thought waves for a nanosecond and, poof, it’s gone. And the rest of them are thinking, “Wish I could wear a hat like that”.

Fear of judgement about something so innocuous as wearing your favorite trilby is just your uncertainty conjuring up a whole lot of nothing. Unfortunately, it’s too easy to allow niggling self-doubts to hold us back when we want to do or acquire something out of our recognized comfort zone, especially something stylishly creative.

It’s not just about a hat. It’s about
  • wearing a chic and trendy outfit that finally makes you feel like your outside matches your inside, or;
  • purchasing an abstract painting that you love-love-love but befuddles your best friend, or;
  • choosing a new car that’s orange instead of the usual white/off-white, because you really like orange.

We don’t have to practice creativity only when crafting or drawing or writing a novel. We can also do it as a matter of style – in public. And it’s not a matter of being brave. It’s more about making a decision to be satisfied and sure about how we are designed – as creative people who are interested in individual style. Or in my case, hats.

Back to the painting at the top of this post. I love this piece because this Crow woman is quite obviously comfortable in her own skin. She’s living out her design which apparently includes sporting cool head gear with joy and confidence. And I get the feeling she’s quite at home making other people feel at home just by being around her.

All that in a smile and a jaunty hat.

Well, and there’s the sunglasses …

Check out for more art that shows off jaunty hats and (not cheap) sunglasses!

If you want to wear a hat now and then but not crazy about what it does for your “do”, check out these hat hair prevention ideas from L’Oréal:

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  • Terry C Hall: July 18, 2023
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    Thanks, Cathy! We’re both enjoying our hats these days! Thanks for reading!

  • Cathy Cloud: July 18, 2023
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    Nice…I’ll don a hat today in tribute!

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