When I was a little kid I developed a serious addiction to television. My parents became somewhat concerned about my viewing tendencies, enough so that the most common punishment I received in my younger days was being banned from watching TV with the rest of the family.
Oh, the travails of our younger years.
As it happens, one of the movies I saw during my early, entirely uncritical viewing experience was “The Flying Tigers,” starring John Wayne. A black and white movie showing on a black and white TV. Perfect.
And although it’s another story for another day, I had no idea that John Alison, a real pilot who flirted with the real Flying Tigers would play a role in my own entry to aviation. Not that John Wayne’s Flying Tigers had much to do with real life or the men and women of the actual Flying Tigers.
In any case, one exchange between characters in that movie stuck with me. At least I think it was that movie. It’s been decades since I’ve seen it, so I could be wrong. Memories do have a tendency to fade and rearrange themselves over time. The conversation I remember had to do with boots. Specifically, cowboy boots.
As I recall it The Duke chastised one of his pilots for wearing cowboy boots in the cockpit. Wayne’s character perceived them as a poor choice for a pilot. His subordinate wore them anyway, with predictably mortal results.

The Duke was never wrong. Not on celluloid anyway.
In real life I’ve only ever known two people who made it a habit of wearing cowboy boots in the cockpit. One is still with us. One is not.
My friend Brad was young and vibrant. He had a great smile, a quick wit, and that easy way of speaking southern boys tended to develop back in days gone by — before the extreme mobility of Americans began to scrub regional accents away.
Unfortunately, my friend and fellow CFI Brad came to an unfortunate end on a short local flight. He was wearing his cowboy boots.
One out of two aren’t particularly good odds from where I sit.

I suspect this is how superstitions start. One thing that’s almost totally disassociated from another appears to develop a link and, before you know it, a flimsy but self-affirming belief system has been developed. Hence, I may put more thought into the combination of shoe selection and flight plans than most people do.
I’m serious, incidentally. I actually do pick the shoes I’ll be wearing for a given flight at least in part based on the aircraft I’ll be flying, the route I’ll be taking, and the weather.
Let me give you a recent example that illustrates my point. Last week I had the pleasure of flying a J-3 Cub on straight floats. The delightfully fabulous Abbie Kellett took up her position as the Queen of the Skies in the front seat. She did the first takeoff and headed north from the calm surface of Lake Jessie, not two miles from my home.
I’ve known Abbie since she was a kid. Maybe as young as I was when I first saw The Flying Tigers. Since then she’s become a commercial pilot and a CFI. A good one, too. She’s pursued and succeeded at some adventures that live on my wish list, never to be realized, I’m sure.
She spent a season flying Cessna Caravans on floats out of the 23rd Street Seaport in New York City. The absolute opposite end of the seaplane spectrum from the little jaunt she and I were taking over the very rural expanse of central Florida. Oh, how I would love to have done what she’s done when I was younger.
The J-3 has a tight cockpit. The space between the front seat pilot’s butt and the sidewall of the aircraft is quite slender. I, on the other hand, am not slender at all. Neither are my feet. And so I wear lightweight, highly flexible, wool sneakers when I fly the Cub. They’re closer to a slipper than a shoe, to be honest. Perfect for the Cub.
A few years back I was teaching a local lawyer to fly in my old 1940 Cub. He discovered that shoe selection was an issue for him, too. After trying out a variety of choices he settled on flying the little yellow taildragger in just his socks.
It worked. His control improved dramatically.

Of course, my Cub shoes aren’t practical for all flights. If I’m flying something a bit roomier and faster, and I plan on seeking adventure farther north, over the generously sized Green Swamp, or south over the Everglades, I wear much more substantial shoes. That footwear is made of far more sturdy leather. Still somewhat flexible so I can feel the brakes and rudder pedals beneath my toes, but more rugged in case I have to get out of the airplane in a non-airport environment for a long, not at all enjoyable walk to a paved road, or a house where I might find help.
If I stray even farther north, to the land where snow flies and temperatures dip into the single digits, I wear high tops with two pairs of socks. Experience has taught me that snow is a beautiful thing…right up until it gets into your shoes.
What I don’t wear, ever, is a pair of cowboy boots. Not in the cockpit anyway. A superstitious holdover from two encounters, one with a motion picture, the other with a guy who might have become a good friend had he been with us for longer.
In truth I’m somewhat partial to cowboy boots. Their easy-on, easy-off design coupled with an almost unlimited variety of colors and designs makes them an appealing choice. I’ve had a pair or two in my closet for years and often on my feet. But not in the cockpit. Not once.
I wonder if John Wayne, or Captain Jim Gordon, his character from The Flying Tigers, would be proud of me or laugh themselves silly at the bar? I guess I’ll never know.
The best shoes for flying a Cub are indoor soccer shoes. They are narrow and have a rounded heel. Regular “sneakers” are made to support the foot while jogging/running, and are too wide for a Cub. Race car driver shoes are also good, but more expensive.
What about Sky King? He wore them in the T-50 Bocat and his 310.
I wore cowboy boots in many different airplanes. There were a few cases that they didn’t work. Heel brakes were sometimes an issue. The only shoe that caught on the metal heel plate was a pair of loafers that lasted only that one flight.
Ariat Ranchers. I have a 7KCAB Citabria with HEEL brakes and no problems in over 340+ hours. Although I did have to fly barefoot first time I flew a friend’s J-3 (no issues other than sore heels when braking). And one pilot was not mentioned. Tex Johnston, the Boeing test pilot that rolled a B707 (probably only one…).
When I started doing Ag flying I had been wearing cowboy boots for many years. I grew up wearing them as the family was in the cotton and cattle business. I wore my boots everyday when spraying in first Pawnee 260’s and later in Cessna Ag Trucks. The heals of the boots provided me the perfect height for the rudder pedals and gave some protection, I felt, if anything were to happen with the aircraft. The pilot that taught me the business, a former Air Force pilot, always wore boots and he and I even had some hand-made from elephant hide (the toughest I have ever known). To each his own but unless the cockpit is cramped the boots do me just fine.
Justin Ropers. Comfortable and low heels. I wear them all the time. 19K+hours now in all sorts of airplanes. No issues. The classic “high-heel” cowboys boots were designed to help the rider stay in the stirrups. Those heels get caught under the rudder pedals with disastrous results.
The most common heel is a walking heel. There are roping/dogging heels, which i would think would require a concerted effort to get stuck under pedals. Most people can’t roll their foot enough to do that.
The “high heel” you refer to is indeed to stay in the stirrup, while standing on them, ie; roping, the sharp angle on the back is to prevent hanging in the ground and breaking an ankle while dogging cattle, hence the names.
Anyone wearing those heels and not working cattle would be of the “rhinestone” variety…hence the name rhinestone cowboy 🤠
I always wore cowboy boots 🤷🏼♂️
Moccasins. Soft soled. Great for Cubs, Champs, my CallAir Cadet.
I cringe when I see a pilot wearing flip flops, sandals, etc. My CFI doing my tail wheel checkout got his loafer caught in the heel brake and taxied my Champ into the commercial sized mower. The airport owner witnessed the event. My instructor begged me to take responsibility to save his reputation. I agreed and forever after was that guy who ran into the tractor. Funny story. But heaven help the unlucky person who needs to get out of a burning airplane barefoot. Or wearing socks only. Just saying… and yes, my CFI paid to repair the wing tip.
Had a girlfriend find high heels aren’t a good choice after she got one jammed between the rudder and brake pedals on a PA-28-161. Fortunately a CFI was with her.
Yes, shoe selection can be important as I discovered one day doing acro in my old Salto. Wearing standard issue sneakers, gyrations resulted in getting the laces tangled up in the rudder pedals. In the semi-reclined snug-fitting sailplane cockpit, it was impossible to free them in flight and difficult even after landing. Had a bailout been necessary, I’d have had to take a fire ax to my knee – not that I know many gliders so equipped.
Aerobatics ==> no-lace footwear!
(and not a bad idea for tight cockpits in general)
Maybe the problem was the spurs. There is only one aircraft that require spurs (not cowboy) for high speed ejection (that I know of). Just saying 😉