Why Don't We Dress Up to Fly Anymore? A Hat-Tipping, Tank-Topped Reflection

As a history and social studies teacher, I spend a fair amount of time wondering why people do the things they do—and just as often, why they used to do them. Take hats, for example. From the 1880s through the mid-1900s, men wore hats like it was their job. Bowler hats, fedoras, top hats—if you were a grown man without something on your head, people probably assumed you were either ill or just robbed.

A group of men gather in 1920, not one of them is hatless.

Then, suddenly… hats disappeared. Not all at once, but gradually, like socks disappearing from the dryer. Why? What changed? Was it John F. Kennedy, the famously hatless president? Was it the invention of car roofs that made ducking under a brim less necessary? Or did the practical purpose (sun protection, class status, and good ol’ fashion) just fade away?

Now, while I was pondering this great hat mystery, another thought hit me—one that connects nicely to the present moment. As I pack for my flight to Germany (river cruise, here I come!), I’m remembering a time when people dressed up to fly. Not just "I put on a clean shirt" dressed up. I mean suits, ties, dresses, maybe even a hat. It was an event. Air travel had some sparkle.

Could it be we dressed nicer because we had so much more room in economy class?

I remember as a young boy, flying somewhere—no idea where we were going, and my mom made us dress up. Nice pants, clean button-down shirt, hair combed, shoes shined. Why? Because, in her words, “You’re a reflection of me. If someone sees you looking like a street urchin, they’ll think I let you walk out of the house like that.” I could almost feel a tag stitched into the back of my shirt: Property of G. Kaplan. If found messy, please call immediately.

It wasn’t just the passengers. Back then, the pilots looked like military commanders, and the flight attendants (then called “stewardesses,” bless them) wore gloves and hats and walked the aisles like they were in a fashion show at 35,000 feet. It was a whole vibe.

Fast forward to today: I’m sitting at the gate, waiting for my flight, and I look around. Someone is wearing pajama pants with Spongebob on them. Another traveler is in full beachwear—tank top, flip flops, and enough sunscreen to grease a dolphin. And honestly? No one seems to care.

Now, I’m not judging. Okay, maybe I’m observing with a raised eyebrow, but I promise there’s no judgment in it. I’m just wondering: What happened?

Did travel become so common that it lost its sense of occasion? Was it comfort that won the battle against presentation? Did sweatpants sneak up on us and conquer airline fashion like a soft, stretchy Trojan horse invading Greece?

Back in the pre-TSA days, you could actually go to the gate to meet someone. And even then, my mom made us dress up a little. Not full-on church clothes, but definitely something presentable. Now we’re lucky if someone shows up to pick us up at the curb without blasting the horn from the carpool lane.

But maybe that’s the key: our culture has changed. We’ve moved from formality to function. From “look good” to “feel good.” We’ve prioritized comfort, convenience, and speed. And, sure, with airlines charging us extra for every square inch of luggage space, no one wants to pack a sport coat they’ll only wear once.

Still, I can’t help but feel a little nostalgic for the days when travel was an event, not a chore. When a flight wasn’t just transportation—it was an experience. Like wearing a hat, dressing up to fly gave us a sense of identity, belonging, and maybe even pride.

As I board my international flight—wearing a button up blue embroidered shirt and khakis, i have to wonder, “What would mom say?”

My outfit of the day picture which illustrates how we no longer dress up to fly.