The Well-Dressed Traveler: What to Wear from Takeoff to Touch Down

Airport lounges are the strangest of all catwalks. 

In the space of 10 minutes, you can see every possible form of attire — from “red carpet ready” to the “lazy sofa Sunday” look. 

Where do you want to appear on this fashion spectrum? 

You’re going to be wedged in an economy seat for the next seven hours, so comfort is king. But as a grown man, you should be aiming higher than Homer Simpson PJs. 

So… somewhere in the middle. Stylish yet comfortable. That shouldn’t be too hard, right? Right…?

If you want some help with dressing for your next excursion — and figuring out what to pack — this field guide is your perfect companion.

The unique challenge of dressing for travel

In your local area, you know how stylish men dress. You know what the weather is like, and what the day could bring.

But once you set foot outside your home turf… well, who knows what could happen. And that means you need to think more carefully about your dress sense.

For any form of travel, ask yourself:

• How long will I need to stay in this outfit? Wearing an Armani suit sounds cool until you reach the 12th hour of your long-haul flight. If you want to look sharp without feeling stuffy, consider switching to lighter, more breathable fabrics (Jack Archer Tech Pants, perhaps?). 

• What climate am I likely to encounter during this trip? That includes both your departure point and the destination. Don’t wear your Bora Bora shorts if you’re flying out of Helsinki — or polar gear for a tropical departure.

• How do the locals dress? Sure, you should stay true to your style identity. But you don’t want to stand out for all the wrong reasons.

With the answers firmly stamped on the front of your brain, let’s open up the style playbook.

Building your travel day outfit

The first day of your trip is usually a mixed bag — stress until you pass security, excitement about what lies ahead, the inevitable energy crash en route, and relief on arrival. Your outfit needs to keep up. 

Here are some looks to try, covering the most common travel-day scenarios.

The “straight outta work” travel uniform

Scenario: Red-eye to NYC, meeting at 9 a.m., your CEO is picking you up.

The key ingredients:

• Layers that work harder than your intern (Legacy Button Down in True White or Light Blue, Jetsetter Blazer).

• Tech pants that look like dress pants (Jetsetter Tech Pants Straight Fit in Deep Blue).

• Shoes made of leather.

This is a tough one. You want to look angelic on arrival, but you’ve got to make it through hell first. The key here is smart layering on top and high-performance pants on the bottom. That way, you won’t be a stinking, creased mess upon arrival.

The "vacation starts now" ensemble

Scenario: Flying to Cabo, trying to look good without trying too hard.

The key ingredients:

• A dress-down shirt… just not a Hawaiian one (True White Anytime Tee, layered with a linen button-up in blue or pink).

• Shorts that work both for security lines and poolside drinks (Jetsetter Shorts — the clue is in the name).

• Footwear that doesn’t make your fellow passengers recoil in horror (canvas sneakers or leather slip-ons).

Turning up to your local airport in a Hawaiian shirt, board shorts, and flip-flops is a form of non-verbal assault on your fellow passengers. Instead, embrace the vacation mood with light fabrics and breezy colors.

The international flight survival kit

Scenario: 14 hours to Tokyo, trying not to look like death upon arrival.

The key ingredients:

• A shirt that won’t boil you alive (Merino wool long-sleeve tee in gray or navy).

• Pants that follow suit (Jetsetter Tech Pants or premium joggers in dark colors).

• Simple comfort for your feet (white sneakers, black compression socks).

Sure, it’s a long way. Yes, your joints will seize up. No, we can’t get you a better seat. But that’s still no excuse to go out in public in glorified PJs. Invest wisely in fabrics, and you can make it through the long flight and still look good.

Destination wardrobes: How to pack like someone who owns a mirror

So, that’s the first day of your trip sorted. We just need to figure out all the other days now.

What goes into your suitcase will depend greatly on your destination and schedule. Here are some examples that might relate to your travel plans.

City break: 3–5 days of pretending you're cultured 

The challenge: Dinners, tourist traps, that club you're too old for.

What to pack: 

• Different shirt styles in neutral colors (Henleys, polos, tees).

• Your favorite smart-casual outer layer (bomber jacket).

• Two pairs of versatile pants (dark wash jeans and Jetsetter Tech Pants, for example).

• Sneakers for pounding the sidewalk and proper shoes for dining and nightlife (white tennis shoes, Chelsea boots).

Unless you’re a member of the Smithsonian Institute, this is the only time you’ll ever spend an entire weekend touring galleries and museums. Make the most of it with a wardrobe that lets you dress up for formal settings, and dress down for your hotel breakfast.

Beach/resort: Hot looks for sunny climates 

The challenge: Pool, beach, restaurants with a dress code you might ignore.

What to pack:

• An array of summery tops (linen shirts, lightweight button-ups, and Tech Polos).

• Quick-dry swim shorts that don’t pre-date college kids (solid colors or subtle patterns, 5–7" inseam).

• Smarter options to change into for dinner (Jetsetter Shorts in Sand Stone, leather sandals, or loafers).

Many guys see the beach as a style-free zone. Somewhere you can truly let it all hang out. Even if you adhere to this code, it definitely doesn’t apply off the sand. Be sure to pack both your swimsuit, and something for the classy beachfront restaurant.

Adventure travel: Indiana Jones, but less ridiculous

The challenge: Hiking trails, questionable hostels, pretending you're outdoorsy enough for this.

What to pack:

• Technical fabrics that won't make you look like you raided the Patagonia store (moisture-wicking tees, convertible pants that actually look normal).

• A packable rain jacket.

• Footwear that can handle both cobblestones and dirt paths (trail runners that pass for regular sneakers, broken-in boots).

• The one fleece or puffer jacket you'll live in (preferably in a color that hides dirt).

• Accessories that serve actual purposes (baseball cap, buff that doubles as everything, sunglasses with a strap).

Your Instagram followers think you're scaling Machu Picchu every weekend. In reality, you're googling "easiest hikes with best views." Pack versatile pieces that photograph well while covered in dust, and which allow you to transition from the trail to the hostel bar without looking like you've given up entirely.

Business trip: Fooling people into thinking you're professional 

The challenge: Conference rooms, client dinners, business casual drinks at the hotel bar.

What to pack:

• Two dress shirts that can survive a suitcase (white and light blue, because creativity is dead).

• One suit that makes you look decent (navy or charcoal, properly tailored).

• The dress shoes you wear for only this (Oxfords or brogues, recently polished).

• Business casual backup plan (chinos, a Tech Polo for that "casual Friday" client meeting).

You've mastered the art of looking competent for exactly eight hours before reverting to sweats in your hotel room. Pack wrinkle-resistant everything and pray the hotel has decent hangers. Remember, the goal is to look professional enough that no one questions your expense report.

Unknown itinerary: The universal travel wardrobe

If you somehow have zero clue where your flight will lead, it’s a good idea to pack for every eventuality. 

Here’s a checklist for a mystery week away:

• 7 pairs of underwear (because laundry is optional)

• 7 pairs of socks 

• 3–4 basic tees 

• 2–3 Jetsetter Tech Pants (different colors)

• 1 pair of dark jeans

• 2 button-up shirts (one casual, one dress)

• 1 versatile jacket or blazer

• 1 pair of versatile shoes + 1 backup

• 1 belt

• 1 watch

• Sunglasses

• Toiletry kit

That’s a pretty solid base, we reckon. If you learn anything more about your destination, feel free to add these extras:

• Beach: Swim shorts, linen shirt, sandals, hat.

• Business: Extra dress shirts, dress shoes, ties.

• Adventure: Lots of layers, technical gear as needed (don't overdo it).

• Cold Weather: Layers, gloves, beanie, scarf.

That should do it.

Trip Type	Tops	Bottoms	Shoes	Outerwear
City Break	Henleys, polos, tees	Dark jeans, Tech Pants	White sneakers, Chelsea boots	Bomber jacket
Beach/Resort	Linen shirts, Tech Polos	Swim shorts, Jetsetter Shorts	Leather sandals, loafers	Lightweight button-up
Adventure	Moisture-wicking tees	Convertible pants	Trail runners, boots	Packable rain jacket
Business	Dress shirts, Tech Polo	Suit pants, chinos	Oxfords, brogues	Navy blazer
Unknown	Basic tees, button-ups	Tech Pants, dark jeans	Versatile shoes + backup	Versatile jacket

Packing strategies to beat the baggage fees 

Looking good when you travel means bringing more than one change of clothes. If you don’t pack intelligently, that could mean paying for more luggage space.

Here are two strategies to help you avoid those overpriced baggage fees.

The carry-on challenge (you versus the overhead bin) 

You can fit a surprising amount in a carry-on case, but only if you maximize the space inside. That means:

• Using packing cubes to keep similar items together, neatly folded and compressed.

• Packing shoes with the heels against the wheels, with socks and underwear stuffed inside.

• Making full use of your “personal item” allowance — put as many non-wearable items in here as possible. 

Stop rolling your eyes. Yes, it's extra steps. Yes, your dad never used packing cubes. Your dad also wore white New Balances with jean shorts. Evolution is real.

One-bag travel (for overachievers) 

It’s definitely possible to travel with just one bag, but you’ll need to make some sacrifices:

• You can only cover one climate zone.

• Wear one pair of shoes, and pack the other.

• Stick to neutral, complementary colors like navy, gray, white, black, and khaki. 

• Wear your bulkiest items on the plane and fill your pockets.

• Wash the essentials in your hotel sink.

In other words, the one-bag strategy is anything but comfortable. But hey, you may prefer mild discomfort over parting with extra cash. We respect it.

Your travel style renaissance starts today

You don’t need a Master's degree to figure out the travel dress code. 

Sure, it’s a little more complicated than choosing an outfit at home. But with some forward planning, you should be able to impress with your sense of style — even when you’re thousands of miles from home.

Just remember some of the key principles from this field guide:

• Select high-quality garments crafted from performance fabrics to enhance comfort without compromising style.

• Consider how garments can be combined to create multiple outfits for your trip.

• Choose versatile garments wherever possible, and pack layers for colder destinations.

• Leave the Hawaiian shirt for the beach (if you must).

Go well, traveler. We’ll keep an eye out for a well-dressed gent, absolutely owning the airport lounge.