Should’ve Been a Cowboy

He stood tall. Tall to begin with, but with smooth leather boots and a dark brown Stetson, the man commanded the terminal. Striding through the airport in dark blue jeans and a sharp blue blazer, he was one part Paul Newman as Butch Cassidy, one part Rip Wheeler from the TV show Yellowstone, and one part the strong, silent Marlboro Man.

Out West, he might have blended into the crowd. But in Philadelphia or Orlando, a man in a cowboy hat and large shiny belt buckle is an automatic head-turner. We don’t get a lot of John Wayne and Clint Eastwood types out in the middle of the day. He looked prepared for anything, everything from driving a large herd of cattle to repairing a lengthy line of fenceposts.

Naturally, my mind flooded with questions. Was he the real deal? A working cowboy? Could he rope and ride—and steal the young girls’ hearts? Or was he just someone playing the part for a flight out of gate B25? A modern-day urban cowboy of sorts—think John Travolta out on the dance floor with Debra Winger. Or more precisely, was he Pee-wee Herman in a pink cowboy hat outside a grocery store riding on an old coin-operated mechanical kiddie horse?

An Airport Soundtrack

Right on cue, country singer Toby Keith took over my internal soundtrack:

“I should’ve been a cowboy

I should’ve learned to rope and ride

Wearin’ my six-shooter, ridin’ my pony on a cattle drive.”

I was tempted to walk over and ask my cowboy friend if he knew Kevin Costner, Sam Elliott, J.R. Ewing—the legendary oil-man villain from Dallas—or maybe Taylor Sheridan, the guy who single-handedly made cowpokes the stars of prime time television.

I wanted to hear him say classic lines like, “You tell ‘em I’m coming… and hell’s coming with me, ya hear!” à la Kurt Russell as Wyatt Earp in 1993’s Tombstone. Or, “You gonna pull those pistols or whistle Dixie?” like Clint Eastwood in The Outlaw Josey Wales.

Big Oil, Bigger Imaginations

Oh, I imagined all kinds of potential stories—the narrative took off from there. I pictured him on a high-stakes business trip trying to get the best of ruthless outlaws, rustlers, and bushwhackers. We’re talking Oil here. Barrels and barrels of Texas crude. (God I so hope it was crude oil, and not the essential oils kind.)

I thought about what I would say if he sat down in the empty seat next to me. “Delayed, huh? Marshall Dillon could teach these airlines a thing or two about treating people right.” But that didn’t feel right. Instead, I just watched.

He had to be 6’4”—maybe more. He stopped to pull a phone cord from his backpack. I swear the two young women sitting across from me, whispering and watching his every move, oohed and aahed. I’m 5’7” on a good day with thick-soled sneakers. Could I pull off the cowboy thing? Right down to the belt buckle and boots.

Probably not. Or should I say, “I reckon not.”

Yeah… I should’ve been a cowboy.

What about you?

Have you ever tried pulling off a look that was way outside your comfort zone—or are you sticking strictly to old running shoes and baseball hats like me? (If I have to dress up, maybe a collared golf shirt.) Drop your signature style or epic style fails in the comments below!

Yes, I should’ve been a Cowboy.

Images by Pexels.