Why we need to bring back airport style

Practical rules for travel, and a look at what people with real style actually wear when they're in-flight.

Oct 10, 2025

Quick note

This is a collab post between us and our homies at First Class Jerk. We’ve been friends for a while and wanted to find ways to merge our style and travel content together on an ongoing basis.

In this issue, we share our reverence for the nostalgia surrounding 90s airport style, and then we delve into conversations with people whose personal style we genuinely respect. It’s a deep dive into the products they use while they’re on the go, and more.

Setting the record straight

Dressing well on travel days is a lost art.

We (at First Class Jerk) spend a lot of time in airport terminals, and we’re always on the hunt for the few (and seemingly fewer with every trip) who manage to get personal style right.

Until that photo of Harry Styles catching a flight at Newark went viral.

Look, we’ve all seen the Instagram reruns about “90s airport style” from the original piece that GQ put out. To be clear, Denzel and Hugh Grant put that shit on! But it feels a bit tired to keep playing old hits if there’s never anything new to show for.

But perhaps there is a changing of the guard. Maybe it’s a signal that #airportstyle’s return is imminent?

Does Harry have the horsepower to lead a broader renaissance in actually caring about how we present at 30,000 feet?

If there is anyone who could lead us to the promised land, Harry is the one. And dammit, do we all need an #airportstyle Lisan al-Gaib to follow…

But why does it matter? you might ask. I just want to be comfortable.

And we hear that.

But looking good while traveling isn’t just about dressing up as much as it’s about dressing with intention. Like you mean it.

In the same way you wouldn’t roll up a dinner reservation looking like you crawled out of the hamper, why should airports get the short end of the sartorial stick?

So, it’s about nailing your uniform.

And having a simple, go-to set of pieces that travel well and make you feel put together goes a long way, both for you and the rest of us.

A few “rules” to consider (from FCJ)

These are more like guardrails, but still.

Start with a cornerstone piece. The right chore coat can do it all—easy to layer for in-flight chills, holds its shape through it all, and dresses up or down.
Then build from the ground up. A pair of broken-in loafers does the trick for us. Versatile and slipper-level comfortable, especially with the right sock situation.
No need to go all the way. We’ll never suggest a full suit and tie, though, from experience, we respect the finance travel hustle. Something close, if you’re looking to elevate things? A relaxed jacket and drawstring pant combo. Buck Mason’s aptly named “Carry-on” collection is one example that gets a lot of love.
And here’s where we get really honest…we at FCJ aren’t stylistic tastemakers and we’re definitely not stylists. But we do give just enough of a damn—and we’ve been subjected to more than enough airport carnage to know what’s worth fixing.

Now seems as ripe a moment as any to bring some real thought leadership on the matter, so we’re passing the baton to our friends from Sprezza—a newsletter about men’s style and how to develop personal taste—to help us decode what airport style looks like when it’s actually done right.

And ladies, there are certainly things that apply to you, too.

A return to the airport

Over the last few years, #airportstyle has been making the rounds, fueled by nostalgic throwback photos from the ‘90s; guys really putting that shit on.

David Letterman in his off-duty sweaters.

Richard Gere in peak silver-fox mode.

Denzel looking like Denzel.

And Boston bros Matt Damon and Ben Affleck giving Logan Airport the ultimate runway.

And while those moodboards have popped up in every corner of the menswear Instagram universe and all across TikTok…

It begs the question: how do you actually get dressed for the airport?

When I was a kid, traveling with my parents, my “fit” was simple: a full sweatsuit. I wasn’t closing deals; I was closing a Game Boy. No business obligations—just sticking to whatever schedule my folks had us on.

But when I got older, traveling solo, then with my wife and son, and occasionally heading straight from the gate to a meeting, I began to think differently.

That’s when I realized: you need a uniform.

Mine? No matter if it’s a 6 AM red-eye or a 6 PM hop, I’m usually rocking some version of a Canadian tuxedo. Denim on denim is perfect for the terminal: planes get chilly, and if turbulence makes me spill my ginger ale, it wipes clean easily enough.

My denim chore coat comes everywhere with me. I layer it over a T-shirt or a grey crewneck sweatshirt I stash in my tote.

People may think it’s insane to wear jeans on a plane, but vintage 501s are the Goldilocks of denim: never too loose, never too tight, always just right for stepping off the plane, grabbing a coffee, and heading into a meeting without looking like I slept in a Greyhound station.

As for luggage: I’m a carry-on lifer. It keeps me honest about overpacking, and I’m not about to gamble with airlines losing my stuff. This hard-shell roller for the basics, Filson twill zip tote for the personality. That tote has logged more miles than some pilots—perfect for an extra pair of shoes, laptop, and dopp kit.

And back before everyone (including me) got TSA PreCheck, my move was loafers: sharp enough to look intentional, but easy to slip on and off at security.

The trick? Rubber soles.

Trust me, you don’t want to spend six hours in leather-soled shoes unless you’re actively trying to punish yourself.

Airport style has been documented for decades, but it’s evolved—and, honestly, slipped for most people. Still, there’s a crew out there who want to look sharp while catching flights.

I tapped a handful of guys who practically live in Delta Sky Lounges to get their take: what they wear, what they never board without, and how their carry-on game reveals their whole personality.

The anatomy of an airport fit

I always pick out a denim shirt or jacket with jeans the night before—to ease my mind and give myself one less thing to think about on the morning of a flight.

For UK-based photographer and content creator Jordan Bunker, the approach is the same: he settles on an airport fit the day before. “Doing this the day of would add to the low level of stress a travel day brings with it—passport, phone, wallet, and outfit decisions are one too many,” he tells me.

He and I are in the minority, though. Copenhagen-based art director Ruben Hughes admits, “I’m in general a day-of decision maker.”

Designer Benjamin Edgar Gott takes the same approach: “I dress in such a uniform in general that I don’t need to plan much.”

And Ethan Glenn, founder of Every Other Thursday, treats airport kits like any other day: “I am a big planner, but not when it comes to outfits.”

The go-to travel uniform

For The Lego Group’s global developer, Kevin Kafesu, consistency is key. He sticks to a uniform from Japanese label Teatora: “Their Packable and Doctoroid series are my go-tos, with a rotation of suits and shirting in fabrics tailored to each trip.”

Beyond technical tailoring, storage in his jackets is another deciding factor: “It has pockets for everything—passport, both phones, AirPods, even an A5 notepad or book.”

Hughes and Bunker take a different approach, leaning into elevated loungewear. Hughes packs his Prada cashmere sweater, paired with pajama pants from Lemaire: “The goal is not to look like I’m headed to the airport while still being comfortable, as a lunch reservation might be waiting for me right when I land.”

For Bunker, comfort takes precedence: “It’s sweats all the way for me when it comes to flights that exceed three hours.” His go-to for long-haul trips is a hoodie and jogger set from Swedish label CDLP.

Gott, meanwhile, keeps things pared back. “I’m sitting in the SkyClub as I answer this, and I don’t look much different than a normal day out,” he says.

He describes his style as “elegantly boring,” built around his Ben Edgar 500s and a worn oxford shirt—a uniform he hasn’t strayed from in years.

Sneakers, loafers, or slip-ons?

From speaking with the fellas, I gleaned that a slip-on is the foolproof option—but not just any slip-on. The consensus: a loafer or a Birkenstock Boston clog.

“Loafers almost always are the move,” Glenn tells me. “Comfy, easy to slip on and off for security, and they instantly dress up any outfit—especially if I’m wearing fatigues and not denim.” Hughes agrees: “I prefer loafers always,” noting that his pair comes from tailoring house, Saman Amel.

“Birkenstock Bostons, always,” Kafesu says, since they slip on and off without any effort. Bunker’s travel combo? “Birkenstock Boston with a cozy sock from a brand like RoToTo.”

Must-have flight essentials

While comfort is key when flying, the guys each had a different take on their “must-have” item before boarding.

For Gott, travel is about leisure: “I avoid working while traveling to make space for the mind to wander,” he says. His iPad is his “leisure computer,” strictly for downloading movies or watching YouTube. “I don’t have my email on it, or calendar,” he adds.

For Glenn, Hughes, and Bunker, noise-canceling headphones are essential. “Traveling isn’t always fun, so having music or a podcast to block out my surroundings makes it more pleasant,” Hughes says.

Carry-on personality: tote, backpack, or roller?

It’s always painful to see guys wrestling shoulder-to-shoulder with their wheel-less carry-ons—a choice that makes travel so much harder, especially if you get hit with a last-minute gate change. While many men stack a tote on top of a carry-on, one brand reigns supreme: Rimowa.

“I usually have a roller suitcase with a massive tote on top, which also doubles as extra space if I end up shopping on the trip,” Glenn says.

Gott relies on his own Ghost tote bag, perched on his Rimowa: “The one I use most often is about 10 years old—it’s the weird trolley one with two wheels they don’t make anymore.”

Hughes uses a leather tote from Celine for his camera gear when flying to shoots, but admits, “I must confess that I also have a Rimowa carry-on—which isn’t practical in weight but looks damn good.”

Kafesu brings his Rimowa Classic Cabin for short trips, but notes that his large Visvim Nap tote “is easier to keep under the seat in front of me, which means I can get to what I need without doing the awkward overhead-bin shuffle mid-flight.”

For photographer Kirk Chambers, it’s the equipment that’s usually with him.

“Most of my travel is for photoshoots,” and tells us, “so normally I’ll have both a tote and carry-on Pelican. I never check my cameras, so those always stay with me in the Pelican the entire trip. The big tote carries my laptop, headphones, notebook, snacks, and water.”

That’s all we’ve got for today! If you've made it this far, thank you for the love.

Drop us a note in the comments and say hello (we read every one!).

And if you’re into this kind of thing, give it a heart so others know it’s worth a read.

Discussion about this post

Ready for more?