Why I Envy Hat People

Do you remember the opening credits for the 1970’s TV show “Charlie’s Angels” where Jaclyn Smith takes off her motorcycle helmet, shakes her head and every strand of hair falls perfectly in place?

I realize that Jaclyn’s impeccable hair in that scene was probably a confection of Hollywood magic, but sadly, hats have been a challenge for me to navigate over the years.

When I was younger, I had fine hair. I had lots of it, but they weren’t the majestic oaks of hair that could bounce back from the slightest bit of wind, humidity, sweat, rain or pressure.

I remember times when I was very young when my mom or my grandmother would say “Come here”, lick their fingers and try to tame one of my many cowlicks. How they could choose just one remains a mystery to me, as I remember my hair was sometimes all cowlicks to the point of looking like a young, male version of Medusa.

But as an adult, the maternal spit was replaced by varying combinations of hair gel, mousse and spray, not to mention engineering skills, to build a hairstyle and to lock it in place. But one minute with a hat on my head was like a pin to a balloon, completely deflating my structure, at a time when flat hair was not en vogue.

Looking back, this most unfortunate genetic deficiency brought out a streak of stubbornness I never knew existed within me. It could have been -40 degrees outside (frankly, a normal winter’s day here in Ottawa), and I refused to wear a tuque of any kind. That was when I started buying ear muffs by the case (for some reason, I kept misplacing them) which kept my ears warm for many blustery winters.

To this day, because of my very round face, if you put a tuque on me, it wouldn’t be an exaggeration to say that I looked like a 53-year-old South Park character. I accept that.

But it’s not only winter headgear that has been problematic for me. Spring, summer and fall hats have been an issue for me too.

Back when Duran Duran hit the airwaves in the 1980’s, bassist John Taylor often appeared in photos in a most dapper fedora, which inspired many of us into our first steps into the world of millinery.

I have a few good friends whom I envy with the greatest of admiration because they have that never-a-hair-out-of-place look with (what seems like) minimal effort. And when they put on a hat, any hat, it looks like a crown on them and they instantly rock it. When they found their John Taylor style fedoras, I was still trying on hats, having my typical Goldilocks-style shopping experience.

Either the hat won’t make it down far enough and sits precariously too high, the brim is too big, the brim is too small, or the shape of the hat makes my round face look even rounder, if that’s actually possible.

Not only is my head round like Charlie Brown’s, I don’t want to boast, but my hat size falls somewhere between medium and large (even though I am a fairly compact 5 foot 5 fellow), so getting a hat that fits and that is in the right proportion to this beach ball of a skull has been problematic.

However, it’s not all doom and gloom. There have been a couple of times I thought I looked cool with a hat.

In the 1990’s I really could rock the “ball cap backwards” look! But it’s not like I could walk into the office and sport that look in a serious meeting with my Director General. It needed to be paired with more casual attire and kept for more casual events.

A few years ago, I fell in love with a little flat wool cap I found in New Orleans that looks like beret with a little brim. Finally, I had found a hat that I truly looked forward to wearing as I thought it was quite flattering, and coordinated well with my late fall/early winter wool coat. But in a weathercasting tour-de-force, where the predicted light snow flurries turned 180 degrees to heavy rain, I did not realize that my cool hat would shrink when exposed to water.

It’s a couple of years later and I am still trying to stretch it back out to fit my mammoth Elmer Fudd head and I still curse at the weather forecasters every time I try.

It was after a brush with a mild form of skin cancer, that things changed. Sun safety became my mantra and finding a proper sun hat was the top priority. On a trip to New York City, my partner and I went to a hat store to get professionally and properly fitted hats. I am very happy with the one chosen for me and I wear it quite a bit.

But oddly, that was when I stopped caring about finding the perfect hat. Maybe I was overthinking the process, being overly analytical and overly critical. Instead of focusing exclusively on a hat’s fashionable merits, my priority shifted toward practicality and sun protection.

And then for some reason, somehow, the world changed. Now, hats are finding me and I started enjoying hats.

A dear friend gave me a wonderful Tilley hat that has since accompanied me on many sunny walks. I enjoy it so much, I almost feel naked if go walking without it. Paired with a pair of dark sunglasses, I feel incognito, like a celebrity on the run from the paparazzi. I think I look pretty cool in that one, plus it is perfectly portable and crush-proof.

I was also pleasantly surprised with the hats I get at the running store. Not just one model, but several models fit well and are in perfect proportion to my planet-sized head. The best part is that they are completely washable.

Maybe it’s a little of the over-50 confidence thing that has kicked in as well, but if I want to wear a hat, I wear a hat. Worrying about “how I look in this hat” won’t keep me safe from the sun. And let’s state the obvious, with the every-two-weeks clipper cuts, it’s not like my hair gets messed up anymore.

Let’s not kid ourselves, there are some hats that don’t look good on me. But it seems that there is a growing number that are flattering and that I enjoy wearing.

Maybe I’m just late to the party and it took 53 years to possibly become a hat person myself.

Who knows, maybe I’ll finally stumble upon a John Taylor style fedora that actually fits me. Better late than never!

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Sincere thanks for reading!
Have a great day,


Filed under 50+, Humour

4 responses to “Why I Envy Hat People

  1. Pingback: The Final Cut: From Clippers to Shaver | It's the Journey

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  3. Pingback: 25 Worries about Hair… When I Had Hair | It's the Journey

  4. Pingback: Top 10 Advantages of Clipper Cuts | It's the Journey

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