You’re moving swiftly through a sunlit terminal in 1964, shoes shined, a tailored blazer draped over your arm, and a matching set of luggage rolling behind you. The air smells faintly of roast beef and martinis. The crew looks like movie stars. Boarding feels like stepping onto a film set. It’s all anticipation, all possibility. Now, fast forward to today: a sea of sweatpants, endless security lines, and a lame bag of pretzels (if you’re lucky). Flying has become a test of endurance, not a cause for celebration. It’s more sandwiched in 38B than sipping champagne in the clouds.
But here’s the thing… it doesn’t have to be this way. You don’t need a Pan Am ticket or a trust fund to bring back the ritual, style, and pleasure of jet-setting (even if you’re stuck all the way in the back). Here’s how.
Travel in the 1960s wasn’t just about getting from point A to point B, it was about savoring the journey itself. People didn’t dress up just for show, they did it because flying was a privilege and a rare occasion to step out of the everyday and into something extraordinary. The anticipation started days before the flight: planning outfits, matching luggage, and mapping out the journey with handwritten itineraries. The airport was a stage, and everyone was playing their part.
Onboard, it was a sense of occasion. Meals didn’t consist of slamming $19 sandwiches in your mouth… they were ceremonies. Imagine asking for “a slice of brie, some grapes and two bananas,” and having the steward rolling the cart right to your seat, leaving it there so you could help yourself. In fact, there was so much leg room that you could practically host your own cheese tasting. (Reddit, r/TheWayWeWere)
The crew, dressed in pillbox hats and silk scarves, moved through the cabin with grace. Passengers mingled in lounges, wrote postcards, and made new friends over martinis. The rituals, such as dressing up, savoring a meal, and striking up a conversation, elevated the experience… turning routine travel into something memorable.
Don’t take it from us, this person lived it:
“It was certainly more elegant; people got dressed up to fly, and other people used to go to the airport just to look at them. You also were not subjected to the indignities of a security search. Standing in line is definitely not elegant.” — Reddit, r/SnapshotHistory
The point was that if you’re going to spend hours suspended between places, you might as well make it feel like an occasion. It’s that spirit that we have to revive.
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You don’t need to cosplay as Don Draper or Cher, but trust: a little effort goes a long way. If you want to encapsulate the 1960s jet-setter wardrobe, you have to think tailored blazers, loafers, a silk scarf, sunglasses, and a classic watch. Dark neutrals, a crisp shirt, and a scarf that doubles as a pillow for your mid-flight nap.
If you’re asking yourself, why bother? It’s because dressing up changes your travel mindset and sometimes even your seat assignment. As Eva Chen, Instagram’s Director of Fashion Partnerships, says in Vogue: “I always wear a blazer and pack a scarf when I fly. People treat you better, and you feel like you’re part of something special—even if you’re just in economy.”
Modern brands nailing the look: Jordan Monogram Duffle, The Brown Collection by July, Eastpak Resist’r, and ASICS Skyhand OG. Or hunt vintage if you want the real deal.
Coordinated luggage isn’t just for Instagram. It’s for sanity. Invest in a hard-sided carry-on, a weekender, and a dopp kit (for some reason I always called them toiletry bags, but I heard my fiancé call it a dopp kit for the first time last week... I guess I’m more naive than I thought haha) that makes you feel like you’re going somewhere worth going. Packing cubes, garment bags, and a travel kit (think Pangaia notebooks or a W&P Carry-On Cocktail Kit… yes, those are real and TSA-approved) will have you breezing through security and looking good doing it.
Business or leisure? Pack for both, and blend the lines. A blazer that works for meetings and martinis. A scarf that’s equally at home in a boardroom or on a beach.
Product recs: Pangaia, July, Gucci (1970s Tennis), and Cortiez
The golden age was all about ritual, but this isn’t just about copying the past. These small acts, packing a book, queuing up a playlist, even mixing a classic cocktail, are about making the journey feel intentional, memorable and a little more fun. Rituals are what turn a cramped, anonymous journey into a personal, memorable experience. They’re small acts of care that remind you: you’re not just cargo, you’re a traveler.
Start with a pre-flight playlist, a reading list, and maybe a classic cocktail. In-flight, go for comfort and style: silk sleep mask, linen handkerchief, a real pen (for customs forms, journaling, or just feeling like an adult), skincare, and a good book.
Eat well, even in coach. Skip the sad snack box and pack your own cheese, fruit, and a square of dark chocolate. Channel the trolley cart (minus the kid kicking and screaming behind you).
Remember when people actually talked to each other on planes? You probably don’t. But it was like that in the 60s. And the lost art of the airport lounge and in-flight conversation is due for a comeback. Even in economy, you can be the person who brings a little charm: a thank-you note for the crew, a small gift for your host, a smile for your seatmate.
Create your own sense of occasion even in a crowded terminal. If you’re passing through JFK, check out the TWA Hotel for a dose of retro glamour. Or, if you’re in Phoenix, The Carry On bar takes everything from vintage air travel and packs it into a beautiful lounge.
Flying can be special again if you want it to be. You can be the person who brings style and intention back. The golden age isn’t gone, it’s just waiting for you to roll your suitcase down the jet bridge and bring it back to life.
You don’t need a Pan Am ticket or a private jet to travel with taste. Make every trip, even a quick business hop, feel intentional and elevated. Nostalgia isn’t about living in the past; it’s about bringing presence and pleasure to the present. It’s up to you to take on this mindset for your next trip and transform your journey.
Ever wondered what it actually looked like to order martinis at 30,000 feet or stroll through an airport before sweatpants took over? Check out the images we pulled together from the golden age of flying...
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