Top Comfortable Clothes For Traveling

Last Updated: May 23, 2021

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Air travel is not always comfortable, and you may ask yourself the question: what are some comfortable clothes for traveling? Wearing comfortable clothes is especially important to me when I fly overnight. In this article, I recommend travel outfits and comfortable clothes to wear on long-haul flights.

The Golden Age of Air Travel vs. Today

Back in the day, airplane travel was a special occasion and passengers would pay close attention to their style and “airport outfit.” I still see the occasional passenger board a long-haul flight wearing a suit and tie, but those people usually sit in first or business class and change into a nice cozy outfit once the plane is airborne.

The other extreme is the guy who shows up in pajamas (or sweatpants that look like pajamas). I travel over 100,000 miles per year and have tried a lot of different clothing options, depending on the class of service I was traveling in.

Related article: The Best Travel Gadgets for Techies

Dress Appropriately

When I travel in business or first class, I usually wear at least a pair of good jeans or slacks and a nice shirt. On long-haul or overnight flights I change into pajamas or sweatpants, especially on planes with seats that convert into beds.

However, most of the time I travel in coach, which means tight and very uncomfortable seats. When I first published this article, I was sitting on a train from the Munich Airport to Salzburg, after having spent 8.5 hours in what felt like the most uncomfortable Comfort+ seat on Delta Airlines. Fortunately, I was able to get some rest even though my butt and legs fell asleep as soon as I sat down.

What to wear on a plane or long-haul flight to travel comfortably
My new pants in action

How to Fly Comfortably in Economy Class

When picking my travel outfit, I look for comfortable travel clothes that are:

  • Breathable and moisture-wicking. Depending on the type of plane and the season you travel in, you may sweat (a lot)—especially in the areas of your thighs and lower back. The more moisture builds up, the more uncomfortable you get.
  • Stretchable. Pants made from non-stretch fabric can restrict your range of motion and blood flow. For men, that’s particularly uncomfortable in the groin area. I look for pants that stretch easily and prefer ones made from a four-way stretch fabric.

For my first attempt at finding the perfect travel outfit, I picked a pair of KÜHL Konfidant Air men’s travel pants, a long-sleeve shirt from Under Armour and a super-light KÜHL Spyfire down jacket.

KÜHL Konfidant Air Pants

Last year, on another Delta flight to Munich, a couple who was sitting in the row next to me was wearing KÜHL pants. I took note of the brand, which I hadn’t heard of up until that point, and looked it up a couple of months later.

KÜHL Konfidant Air pants
KÜHL Konfidant Air pants

To me, pants are the most crucial part of an air travel outfit as they can be restricting and thus become very uncomfortable very quickly. KÜHL pants are neither! They seem to have a perfect fit, with sufficient room in the “critical” areas. They also have hidden air vents, so you don’t sweat as easily. But the main reason why I decided to buy those pants was their fashionable look—which is especially impressive considering they are outdoor pants. To me, Konfidant Air pants are one of the best and most comfortable pants I have worn on an airplane yet.

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KÜHL Spyfire Down Jacket

KÜHL Spyfire down jacket
KÜHL Spyfire down jacket

I prefer to travel light, which is not easy in winter as I usually need to pack a warm coat. For an upcoming one-week trip to Austria and Switzerland, I wanted to get a soft-shell travel jacket, but REI didn’t have the one I wanted. The sales associate recommended a down jacket instead, and I fell in love with the KÜHL Spyfire.

It’s stylish, ultra-light, water-resistant, and when rolled up it’s the size of a large grapefruit. As a result, it only takes up a little bit of space, which makes it easy to carry on to a plane.

And I can even stuff it in my backpack or pack it in my luggage if needed. At the same time, it’s warm enough to keep you cozy in temperatures around freezing when layered with a shirt and sweater or pullover.

I had planned to wear it with an Under Armour shirt as a base layer and a fleece sweater. I forgot to pack the latter, but the jacket kept me warm on the plane and while I was waiting at the train station, despite the wind and temperatures hovering just a bit above freezing.

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Under Armour Shirt

My complete outfit
My long flight outfit

I usually opt for moisture-wicking shirts during air travel, and Under Armour is one of my favorite brands. Most airplane seat covers aren’t very breathable, so it’s essential to move moisture away from your body.

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What to Wear on a Plane in Summer

I originally wrote and published this article during winter with cold-weather travel in mind, as you can tell from the comfortable clothes I was wearing in the photos. So I wanted to take the opportunity to update it with stylish outfit tips for what to wear on a plane in the summer.

Even during summer, I wear long pants when I travel internationally—especially on overnight flights. REI recently had a sale going on, and I used that opportunity to get a second pair of KÜHL Konfidant Air pants.

ExOfficio Dylan Jeans

I also got to try the fantastic Dylan Jeans by ExOfficio. They look like regular jeans, but they stretch and are incredibly comfortable. They also have a hidden pocket to carry your passport as well as a second stealth side pocket. As a result, they are about as practical as cargo pants without a lack of style. These have become a permanent addition to my collection of travel clothing.

Depending on your job, they are also perfect for the office. I work from home and sit all day in front of the computer. Before the Dylan Jeans, I usually wore gym shorts. But my wife got sick of my “office look” and asked me to wear something more fashionable from time to time. The Dylan Jeans fit that bill perfectly and made it easy to improve my style—believe it or not, they’re just as comfortable as my gym shorts.

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Lululemon Shorts and Pants

Lululemon Kahuna Golf Short II
Lululemon Kahuna Golf Short II

A few years ago, I got a Lululemon workout shirt for my birthday and it became one of my favorite shirts for doing CrossFit. So I recognized Lululemon as a good brand of workout clothes, but it never occurred to me that they also offer stylish outfits for flying.

While looking for an alternative to my Dylan Jeans for hot summer days, I stumbled across a lightweight four-way stretch fabric Lululemon calls Warpstreme, which is also sweat-wicking and quick-drying.

The company uses that fabric in various pants and shorts, but the ones I highly recommend are Sojourn Pant or Kahuna Golf Short II.

I wore Lululemon shorts a few weeks ago when traveling for business to Switzerland. I usually avoid wearing shorts on overnight flights because it tends to get cold aboard most airplanes, but the fit and comfort of those shorts outweighed any temperature concerns I had before boarding the flight.

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Lululemon Metal Vent Tech Long Sleeve Shirt

Lululemon Metal Vent Tech Long Sleeve Shirt
Lululemon Metal Vent Tech Long Sleeve Shirt

I just got the Metal Vent Tech shirt a few weeks ago, and I love it. I originally bought it for working out, but it’s so lightweight and comfortable that I decided to use it for travel instead. I recently wore it on a flight to Zurich, and it was perfect. Despite being summer, the shirt was neither too hot nor too cold. I even felt comfortable wearing it in Atlanta when it was 90 degrees and full sun. It’s also available in a number of different colors.

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I have come to appreciate the KÜHL RENEGADE shorts* and matching STYK shirt when it’s hot outside. Both are incredibly comfortable and dry quickly.

On a recent business trip to Orlando, my boss’ wife talked me into joining her for a session of Crossfit at the local gym. I didn’t pack any gym clothes but figured the RENEGADE shorts would do. So I worked out twice with those shorts and washed them by hand after each session. Thanks to their moisture-wicking and breathable fabric, the shorts dried within hours and I could use them the next morning again.

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What to wear on a plane or long-haul flight to travel comfortably
Michael after a CrossFit session wearing KÜHL shorts.

What Shoes to Wear on a Plane

Comfortable shoes are one of the essential pieces of clothing when traveling. But traveling comfortably doesn’t that mean you have to give up style!

My Favorite Three Pairs of Shoes for Traveling

If you ever meet me at the airport, chances are I will be wearing one of the pairs of shoes on the list below:

  • FRYE Men’s Chambers Low Fashion Sneaker
  • Johnston & Murphy Shaler Slip-On Dress Shoes
  • Paul Evans The Legend High-Top Sneaker

FRYE Men’s Chambers Low Fashion Sneaker

FRYE Chambers Low Sneakers - Comfortable sneakers
FRYE Chambers Low Sneakers

I have had these FRYE leather sneakers for many years, and they are arguably the most comfortable pair of walking shoes I own. They fit perfectly, feel like wearing socks, and I don’t want to take them off. Usually, the first thing I do when I get home is to take off my shoes. With these sneakers, I often don’t bother and just leave them on.

Classic low-top styling meets sporty polish by way of slightly tumbled full grain Italian leather. Your new wear-with-everything go-to when keeping things casual cool.

The Chambers sneakers are made from Italian leather and have a good leather lining and outsole. The only thing I am not a fan of is the rawhide leather laces. I just don’t like the feel when tying them, but that’s just a personal style preference.

I’m a member of the Global Entry and TSA Pre traveler programs, so I usually don’t have to take my shoes off when I’m walking through airport security. But I’ll admit that if I wasn’t part of those programs, shoes with laces could be an inconvenience.

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Johnston & Murphy Shaler Slip-On Dress Shoes

These are the three most comfortable shoes for traveling I own
Johnston & Murphy Shaler Slip-On Dress Shoes

When I travel for business—and especially when I go to trade shows where I have to stand all day—I wear my trusted Shaler Slip-ons.

Crafted of premium polished calfskin with full leather lining and a cushioned insole for comfort, this Shaler slip-on from Johnston & Murphy is a classic, timeless must-have for any professional man’s wardrobe. The Bondwelt construction provides a clean, dressy look, while the combination leather and rubber sole with Flex System technology provides comfort and lasting wear. It was designed with a trimmer, modern profile that’s destined to be a new favorite.

Johnston & Murphy have equipped these stylish dress shoes with a memory foam cushioned insole, and because they don’t have laces, it is super easy to take them on and off. They are made with a premium calfskin leather upper and a soft sheepskin lining.

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Paul Evans The Legend High-Top Sneaker

These are the three most comfortable shoes for traveling I own
Paul Evans sneakers are ready for Europe!

I wore these stylish sneakers for almost 24 hours nonstop during a recent trip to Europe. What speaks to the sneakers’ comfort is the fact that I never felt like I wanted to get out of my shoes. They are super comfortable to wear, which is a key characteristic of good travel shoes. And I love how they look; to me, they have a particular “cool” factor.

We produce small batches of handmade luxury men’s footwear in Naples, Italy. Due to the limited quantity of the finest Italian calfskin leather available and the handmade production of our collection, we frequently run out of product.

The sneakers are handmade in Italy with full-grain Italian calfskin leather and feature a good leather lining.

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Maintenance Tip

You have to properly maintain your leather shoes if you expect them to last for many years. I am not big into polishing shoes, so on the way back from a trip, I usually get my shoes polished at the airport. That costs $8-10, but I consider it an investment in my footwear.

Related article: Proven Tips on how to Overcome Jet Lag Quicker with AYO


Cabeau Evolution Memory Foam Travel Pillow
Cabeau Evolution Memory Foam Travel Pillow

Besides comfortable travel clothes, you may also want to add a neck pillow to your packing list for long flights. My vertebrae get sore when I use a neck pillow for too long, but the best one I have found is the Cabeau Evolution Memory Foam Travel Pillow. It provides excellent head support on four sides, and it comes with a bag to carry it in.

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Best Travel Outfits for Planes

Stylish travel outfits that are both functional and comfortable can make long flights much more bearable, especially if you fly in coach. While I may wear sweatpants and flip-flops to go grocery shopping on a Sunday morning, I make an effort to not look like I just fell out of bed when boarding a plane.

The good news is that brands like ExOfficio, Lululemon, and KÜHL offer plenty of stylish outfits for your travel wardrobe. In fact, most of my new travel clothing fits better and is more comfortable than my sweatpants.

What’s your go-to, stylish yet comfortable outfit for airplane travel (especially when it comes to long haul flights)? Let me know by leaving a comment below!

6 thoughts on “Top Comfortable Clothes For Traveling”

  1. Fantastic list and i have got so many little tips from looking at them to use on my own site…Thank you so much for this!

  2. Gary, are they really so cool as you described? I have a great addition to this trousers! Shoes more, they will match to the general look and you will feel cozy and comfortable.

  3. Took your advice on the Kuhl trousers, fantastic. Flight from Glasgow to Sydney. Konfidant air were very comfortable, and will be great for the hills on hot days (even in Scotland) Thanks again.

  4. Thank you, some very good advice on Long haul travel that will be very useful to me soon. Good shout on the Kuhl trousers, gonna try and source a pair in my size.
    Thanks again

  5. Here’s an interesting bit of history. When Reagan was beginning his campaign for President, his campaign team wanted to take pictures of him outdoors at his ranch and often riding on horseback. Reagan assumed, as a matter of course, that mean wearing the most comfortable attire for riding horses, pants that are extremely baggy at the upper leg. His staff convinced them that, while that may be true, most Americans, who knew nothing about horses, would see that as very upscale. So Reagan was photographed in what most Americans thought he should be wearing—traditional blue jeans.

    I wonder if there’s a similar gap between what travelers feel they should wear to appear respectable and what would actually be most confortable for hours spent sitting in closely confined seats. Your Konfidant Air pants are an illustration that comfort on flights doesn’t mean dressing in clothing that looks like PJs.

    Perhaps there’s something about flexibility in outdoor activities that makes them also adapt well to sitting for hours in an airplane seat.


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