Cowboy Lids


I know you have more important questions, but I’ve seen pictures of you wearing a cowboy hat and want to ask if you think it’s stupid for me to wear one? My brother says I will look stupid.

Thank you,


Your brother doesn’t love the Lord.

I am a Resistol hat man myself. And it is my firmly held opinion that we need more kids in this world wearing behemoth headgear and dressing up like Willie Hugh Nelson.

Our nation’s forebears wore broad-brimmed, high-crowned hats; from the Pilgrim days to Burt Reynolds. Even the pope has his own enormous hat. So why shouldn’t you?

Take me. I’m no cowboy. Not even close. I am what you’d call a middle-aged homeowner with a 30-year-fixed mortgage. I don’t own a horse or live on a ranch, although my wife says my truck smells like a substance common to barnyards. But none of this matters because the main reason I wear a cowboy hat is this:

It works.

For years I worked on construction and landscaping crews. We baked out in the sun all day, and ball caps didn’t cut it. In Florida, baseball hats are about as useful as ejection seats in a helicopter.

With a standard ball cap your neck and lower face remain exposed. And speaking as a card-carrying fair-skinned redhead who can develop third-degree sunburns in a movie theater, I need total coverage.

The second reason I wear the big hat is because I come from rural people, cattle people, livestock auctioneers, VFW bingo champions, and septic-tank installation specialists. These men wore tall hats with wide brims, and there was nothing unusual about it.

I received my first cattleman’s hat when I was very young and I never took it off. I have early photographs of myself wearing a diaper, sucking my thumb, and sporting a Resistol hat for my mother’s Bible study group. The church ladies said I was the cutest 26-year-old they’d ever seen.

But enough about me. Let’s talk about why you need a cowboy hat:

For starters, you’re American. The United States has approximately 9.5 million horses, which is exponentially more than any other country. So technically, this makes you a horse guy.

And bonus, Florida ranks third for having the most horses in the nation. If you don’t believe me, just visit Ocala; they ride horses to the DMV.

Also, you come from a society that currently and historically produces more commercial beef than any other country, so in a way you’re also a cowperson.

Simply put, you hail from a nation that was built by people on horseback, and our ancestors didn’t wear propeller beanies.

Certainly, some narrow-minded people might tell you that wearing a cattleman’s hat in public looks out of place, but these are mostly youngish city dwellers who—hard as this is to believe—have never even seen a Winston Cup Series.

Still, try to remember, not everyone is a towny. Some of us come from families who actually had dinner-time conversations that involved topics like manure spreaders, or the issue of cannibalism among poultry.

And we’re not alone. In the U.S. right now one out of every five people are from rural areas.

Believe me, people still wear cowboy hats non-ironically. I have friends who are drywallers, lawyers, pipe fitters, peace officers, neurosurgeons, roofers, respiratory therapists, mechanics, college baseball players, university professors, and beer-joint musicians, and they all wear taco-shells.

In our part of the world some law enforcement officials still wear cattleman’s hats with their uniforms. Over in Clay County, Florida, for instance, the sheriff’s department had a voluntary uniform policy wherein officials wore cowboy hats.

And before you write off Clay County as some backwoods county, Clay County also happens to have Florida’s only current female sheriff: Michelle Cook. So put that in your Stetson and twirl it.

Personally, in my travels as a writer I have proudly worn my Resistol 4-Star Genuine Shantung hat in nearly every state, and in countless airports. I’ve donned my headwear in major cities like Los Angeles, Philadelphia, and Detroit.

And do you know the main thing I’ve learned in these big-city exploits? Muggers will assault you no matter what’s on your head.

But my most fun hat story took place a few years ago when I wore my hat to New York City for an author event. As soon as I deboarded my plane in LaGuardia Airport, I was swarmed by a gaggle of kids wearing blue shirts, jeans, and ropers. They all seemed so excited.

The kids were representing the National Future Farmers of America. We all got our pictures made together. Every child wore a ten-gallon lid that was nine times the size of his or her head.

One overjoyed kid shook my hand and said, “Are you a big-time country music star?”

“No,” I said. “Sorry.”

He let go of my hand. “Well, what are you?”


They avoided eye contact with me after that.

So you don’t need anyone’s permission to be yourself. What you need is bravery. It takes bravery to be who you are in this world.

Sure, a four-inch brimmed buckaroo might feel awkward if you’re not used to it. But keep reminding yourself that you’re an American kid. You come from a culture of men and women who overcame insurmountable odds, dire circumstances, global wars, and pandemics, and still managed to give the world the sacred gift of Willie Nelson.

So write me back and send me your address and hat size, hoss.


  1. Sandi. - May 28, 2021 8:15 am

    Let’s hope this young teen does send you his address, followed shorty thereafter with a photo of himself wearing his cowboy hat!

  2. joan moore - May 28, 2021 10:40 am

    Best hat store?

    • James Woods - May 29, 2021 3:29 am

      Charlie 1 horse….I don’t leave home without it.

  3. Michael Reese - May 28, 2021 10:48 am

    This was SWEET! THANK YOU, whoever you are.

  4. Debbie g - May 28, 2021 11:06 am

    🤠🤠🤠🤠love hats too even on my smiley faces. Be brave we are all one of a kind great lesson

  5. Susan Norman - May 28, 2021 12:05 pm

    Once again my morning is off to a good start. Enjoyed the story, Thank you!

  6. Darlene - May 28, 2021 12:59 pm

    There’s something about a man wearing a cowboy hat that makes a lady’s heart beat a little faster… I don’t care who you are, or what you look like, if you’re wearing a cowboy hat, you are one handsome buckaroo! This is from a grandma, so listen to the advice of your elders, young man, and the girls will be falling all over you! 🤠

  7. Helen De Prima - May 28, 2021 1:18 pm

    Well said! Nothing looks as cool as a man in a cowboy hat. We live in New Hampshire, and my husband has a Stetson for winter and a Resistol signed by several bull-riding champions to wear to PBR events. Yee-haw!

  8. wuf - May 28, 2021 1:40 pm

    Great column.
    Winston Cup Series??
    A man with history. Rock on.

  9. Katie McCarty - May 28, 2021 1:52 pm

    The best one ever. ! You made me laugh before breakfast this morning! The best one l have ever read! Thank you

  10. Becky - May 28, 2021 2:22 pm

    My grandfather, who passed away sometime in the 1930’s – way before I was born – wore a black Stetson. The only picture I have of him shows him beside his horse and he, not the horse, is wearing the Stetson. When my grandmother passed away, I became the recipient to the hat – I don’t know why, but I did, and I still have it. The band is a bit worn and just a little soiled, but the hat still curls up on the sides and is as soft as velvet. This cowboy hat is a reminder of the man at the top of my Family Tree, who didn’t know me, but gifted me with a part of his life and his history. Thank you, Sean, for another great advice column…I hope the 14-year-old wears his hat with as much pride and love as you do!

  11. LBJ - May 28, 2021 2:23 pm

    Many years ago my husband had a business trip to Dallas. It was school vacation week so I got to go. I bought myself a pink cowgirl hat.
    There is a major fundraiser for cancer in Massachusetts called the PMC. It it’s a 192 mile, 2 day bike ride that happens the 1st weekend in August. It raises millions of dollars for cancer research and all the money goes to Dana Farber. Last year, for the 1st time, the official ride was canceled. Those riders still raised millions of dollars doing a “reimagined” ride.
    This year the ride is on! I don’t ride, but have been a volunteer for years. I will happily be at the bottom of the Bourne Bridge, greeting the riders to Cape Cod by 4:30 AM. They can always spot me… my pink cowgirl hat as I shout, “Good Morning! Good ride! Wicked hard right at the bottom of the road!”
    Let’s beat cancer!

  12. Sharon Brock - May 28, 2021 3:01 pm

    Hanging on a wall in my apartment is the last formal Stetson my Gramps wore 41 years ago. His straw one went to another sister. My Texas grandfather was never seen outdoors without his Stetson. When he entered the house or church, there was a designated resting area for said headgear. One of my favorite memories.

  13. Patricia Gibson - May 28, 2021 3:11 pm


  14. Susan Corbin - May 28, 2021 3:19 pm

    A wonderful story! I love cowboy hats on males and females. I think it looks classy.

  15. Linda Moon - May 28, 2021 5:10 pm

    I began to wonder immediately as I read about your audacious pronouncement of the brother and our Lord. Wonder often leads to unexpectedly good things. A cute red-headed guy from the culture of hats took me to a Willie Nelson concert, and I’ve never been the same since. I digress….and then I continued to read about permission and bravery to BE YOURSELF. Please let us know if you hear from hoss himself, Sean. I hope he’ll be wearing the hat soon!

  16. Joann Wilson - May 28, 2021 9:16 pm

    This one was so GREAT! It was funny and awesome! It was delicious!

  17. Ken - May 28, 2021 10:40 pm

    I served 28 1/2 years in the military and wore my “Garrison” hat with pride. After retirement in 1980 i switched to the Cowboy Hat out of necessity,since we average 13 1/2 Feet of rain per year, and since Baseball Caps only cover the face, I obviously needed protection from the rain flowing down my neck. People in my current hometown recognize me by my “Cowboy” hat. I grew up in Florida and in those days they were not so prevalent in the town I grew up in.The comment about Ocala is right on, it’s definitely Horse Country” The central part of the state is also Cattle Country and cowboy hats are common.

  18. Trisha Knudsen - May 28, 2021 11:41 pm

    I love your writing so much – new to the crew, but have enjoyed every single thing I’ve read by you. And I know a little about writing, being a poet for nigh on to 47 years (I’m 61). My Mama hails from the beautiful mountains of Virginia and was a gen-u-ine hillbilly, so them mountains is in my blood. All you write I feel deep in my bones and slide right up into my gushy heart. Thanks, Sean. I tip my stetson to you, Sir! Trisha xo

  19. dolphindigs - May 29, 2021 4:04 am

    Sean, you’re a good man.

  20. Cathy - May 30, 2021 1:16 pm

    Another great story, Sean. I like hat guys and gals too. I come from four generations of North Florida farmers who always wore hats, and my 95 year old Daddy still puts his on to go outside. One thing you didn’t tell the young Tampa fella is that people will recognize he is a Southern gentleman if he removes his hat inside a building, especially in a restaurant. It irks me to go into any restaurant or group gathering and see men with their hats on. It’s just the way I was raised. And I think men still need to be taught to open the door for females and stand up when a new female enters a room. Those were manners that demonstrated the polite society that Southerners had for centuries.

    • Ken - May 30, 2021 6:15 pm

      Yes,Cathy It bothers me as well that the clods of today and the past generation too have no respect for the “niceties” of a civil society.I always remove my hat when I enter a place of worship,and anywhere there are others present indoors. I lost my wife of 47 years just 3 years ago, and she ALWAYS was shown the respect that she deserved.But then, there are too many examples of disrespect shown to anyone and everyone by the bad examples that we have today. It’s all about ME,ME, ME.I count my blessings everyday that I have an extended family who love and respect me and have given support when needed.Not sure how much longer I have to go before I join the love of my life in the next existence, but I grieve for the world that I grew up in.

  21. Kate - May 31, 2021 1:54 am

    I have a friend who is a real Texas “cowboy” and he has worn his cowboy hat, jeans, and boots, literally all over the world, and somehow, he never looks out of place and it doesn’t matter if he is in New York, Washington, D. C. , Ireland, England, or Rome, Italy, everyone loves him because he is an American cowboy. Of course when he is in Texas, Wyoming, or Montana, he just looks “normal” and is no big deal.


Leave a Comment