For as long as I can remember, I’ve loved visiting new places, and for nearly as long, I’ve loved equipping myself for travel. Not quite as much as I love the travel itself, but pretty darn close. The one aspect of visiting new places I’m not overly fond of is getting there, particularly when it comes to cramming my large frame into what modern airlines claim to be reasonable accommodations for human adults. Because of this, I’m constantly in search of travel gear that mitigates or alleviates the discomfort of air travel. For short trips – 5 or so hours and under – I have the gear list pretty locked in. For longer-haul adventures, I regularly test out new items when travel opportunities arise. Every trip is a learning experience, which raises the most important bit of advice I can offer on this topic: find what works for you.
There are incredibly useful resources out there, like PackHacker, that provide honest assessments of travel gear. I’ve used those resources to inform many purchases, and what I’ve learned over time is that my preferences often don’t align with that of reviewers’. That’s no judgement of them, but an acknowledgement that long-haul travel is a grueling experience, and grueling experiences do a damn good job of surfacing every little boundary of your tolerance. You’ll go through lots of trial and error, but if you pay attention to your own needs, and don’t fall victim to the pressure of conformity, you will methodically piece out your personal travel kit.
I’m not here to tell you what the best of anything is, in an objective sense. Instead, I’ll convey what my preferred pieces of travel gear are, and explain why they work for me. There are many people with more travel experience than me, but I’ve also spent roughly two hundred hours in the air in the past two years, which provided ample opportunity for trial and error.
Personal Item Bag
This is the category I’ve experimented with the most, as I have specific desires for a personal-time bag, which make finding the ideal option more challenging. It needs to carry the essentials (over-ear headphones, earbuds, snacks, meds, cords and chargers, tablet or laptop, water bottle, passport, lightweight hoodie or jacket) without taking up so much space that I can’t fit my feet under the seat in front of me. I also need the bag to be useful at my travel destination, for work or personal activities, and offer organization that makes it easy for me to find things without rummaging around. While I’ve yet to find the perfect option, three contenders stand out.
Spendy
The Tom Binh Co-Pilot has the look of a bag that your job gave you with the laptop that would serve as the anchor slowly, intractably dragging your spirit into the mundanity of white collar work. That deeply unsexy appearance belies solid functionality. There’s a bit of magic at play with how much can fit into Co-Pilot, as it seems there’s always a little bit more space to ingest another item. The sizing is in between a large sling, and a small briefcase, and the design enables the bag to fit under a seat while standing upright. This is crucial, especially for the long-legged and large-footed such as myself, as the position leaves space for feet on either side of the bag.
The Co-Pilot isn’t perfect, as it is missing a dedicated sleeve for a laptop or tablet, though you can still fit either – to a certain size – in the main compartment. You could use a standalone padded sleeve, but doing so takes up valuable space needed for other items. The layout also isn’t the most flexible, even if it is surprisingly spacious – the front side pockets, in particular, are restrictive in their utility. The Co-Pilot is also $168, and $193 if you add the brand’s luxuriously comfortable Absolute Shoulder Strap. That’s a lot of money for a bag that has such a narrow range of use, though Tom Binh does use high-quality materials throughout their products. If you want more space, look into the brand’s Pilot, which employs a similar format at a larger scale.
Midrange
The most recent addition to my travel collection is Bellroy’s Tokyo Wonder Tote (the 12 liter version). Calling it midrange is only possible because of how expensive the Co-Pilot is, as the Wonder Tote is $169, but be patient, as Bellroy has frequent sales. The Wonder Tote has all the style that the Co-Pilot lacks, more space, and more useful organization of that space, including a dedicated internal sleeve for a tablet or laptop. The straps are great for a tote bag, with textured material on their undersides that keep the bag on your shoulder, but they don’t offer the comfort and ease of carry that of the Co-Pilot’s standard strap, nor the Absolute Shoulder Strap. The bag will fit vertically under some airline seats, but even when laid on its side, it affords foot room beneath the seat. The only critique I have of the Wonder Tote are the internal water bottle pockets, which take space away from packing other items, and require you to open the bag to get your beverage. Adding one external water bottle pocket would provide meaningful utility without adding unmanageable bulk to the bag’s profile. Despite this singular foible, this is my Goldilocks pick so far, particularly if your destination includes work, as the Wonder Tote has the style and capacity to support daily professional needs.
Thrifty
If you haven’t shopped at Uniqlo before, you’re missing out. The brand is a champion of affordable wardrobe staples, and they branch out into accessories from time to time. Uniqlo recently released a shoulder bag, aptly dubbed the Multi Pocket Shoulder Bag (MPSB), for the bargain price of $29.90. It is no accident that the bag resembles the Yoshida & Co Tanker, the price of which makes the Co-Pilot seem a bargain. Size-wise, it sits between a sling and a briefcase, which is great for air travel, giving you access to what you need at hand in flight, without consuming a lot of space. Like the Co-Pilot, the MPSB fits lengthwise under a seat, leaving space to either side for your feet. The layout is less restrictive than the Co-Pilot, and the two front pouch pockets are a more useful shape. The water bottle pocket, in contrast to that of the Co-Pilot and Wonder Tote, is an expanding side pouch that doesn’t cannibalize interior volume from the main compartment. The materials, including the ripstop fabric, are of good quality, though a few notches below what Tom Binh uses. Still, I prefer it to the five times more expensive but less functional Co-Pilot.
Carry-on Bag
For short trips – short in terms of time spent at the destination, not flight duration – I can get away with just a carry-on bag. I’ve tried a variety of travel backpacks and a couple of suitcases and landed on the Monos Carry-On as my preferred carry-on for most trips. Overall, I’ve found hard-sided suitcases more useful, as they offer more internal organization and greater long-term durability. My wife has an Away carry-on that is almost interchangeable with the Monos, but the latter has larger wheels that make it roll over uneven surfaces more easily. That said, the exterior of the Monos scuffs much easier than the Away’s, though my preference lies with form over cosmetics.
Monos Carry-on, bearing badges of honor from its many adventures.
If you don’t want to spend what Monos or Away ask – starting at $275 MSRP) – I also heavily used a TravelPro Crew Carry-on Spinner for over a decade. I still have it, and though the material around the telescoping handle has frayed, everything else still works well. Had I not found another, better-for-me option, the Crew would still get miles from me.
Travel backpacks can also be great. Just note that if you have a long layover on your trip, a rolling carry-on is better. Lugging a loaded backpack for hours can be rough, and the last thing you want is for your back and shoulders to be sore before getting on another long flight – I’ve been there, and it isn’t fun. I also don’t love having to sit it on the airport floor when there aren’t enough seats or a table to rest a backpack on. If you don’t anticipate spending hours sitting in an airport, or are heading to a destination that isn’t amenable to wheeled luggage, I have a GoRuck GR2 that is gear perfection. It is on the heavier side for a backpack, but that weight is the result of construction quality that may enable the bag to outlive me.
Clockwise, from top left: Bellroy Tokyo Wonder Tote, Alpaka Tech Case Mini, GoRuck GR2 (40l), Uniqlo Multi Pocket Shoulder Bag.
In terms of how much and what to pack in your carry-on, be honest with yourself about how you want to experience your destination. The internet, particularly social media, is rife with travel influencers who want to push for one-bag travel. I’ve tried it, and outside of a weekend trip that didn’t have multiple scenarios (e.g., work & personal activities), it hasn’t worked for me. If you don’t perspire much or don’t mind carrying a bit of a waft wherever you go, give it a shot and see if you can be a one-bag minimalist. If, like me, you are a human who perspires and likes fresh-smelling clothes, pack what you need and don’t worry about conforming to the trend. It is possible that your checked bag may not make it to your destination, but I’ve been fortunate to avoid that experience despite many opportunities. Just in case, I advise packing a few days’ worth of clothes that are suitable for your destination in your carry-on, in case your checked bag doesn’t make the trip with you, or arrives later than you do. Also, toiletries go in the carry-on, at least the essential ones.
Air Travel Clothes
I won’t recommend the best clothes for your travel destination, because the variance is too wide depending on your destination’s environment, the time of year you are traveling, and what you plan to do when you get where you’re going. The following are what I use while flying, all of which can also come in handy when I arrive at my destination.
My t-shirt recommendation is going to make you mad, because it is very hard to buy one. Oko Lifestyle is a surf shop brand out of the 30A area of Florida, and they have in-house label bamboo t-shirts that are my absolute favorite. They are a heavier weight that provides a good drape, but because they are bamboo, the weight doesn’t make them hot or restrictive. Add on a single chest pocket for in-flight access (my in-flight gum pocket), and you have maximum comfort with a dash of utility.
Your humble author wearing the Oko T-shirt in the sweltering heat of beautiful Nusa Penida, Indonesia.
The shirts aren’t sized and cut consistently, so you have to try them on to see if the one in your hand fits. Sadly, Oko doesn’t do online retail beyond wholesale, so you have to make the trek to one of their shops to pick up one, or many. This isn’t some precious artsy appreciation for handcrafts, though – these are the only T-shirts I wear on flights. For a more accessible alternative, Free Fly makes bamboo pocket tees that are pretty close in feel.
Staying up top, and in the bamboo domain, you’d do well to grab yourself a pullover hoodie from Free Fly. I have a few, one lightweight, and another mid-weight, and they are both excellent. They give me enough coverage to stave off the chills during long flights, but don’t immediately require removal as cabin temperatures rise. Most of their tops also have UPF protection, which has come in handy when I’ve traveled to sunny destinations. As with the Oko t-shirt, Free Fly’s hoodies are incredibly comfortable, and they pack down compactly.
As for bottoms, there are two pairs of pants I recommend. For maximum in-flight comfort, Vuori’s Sunday Performance Joggers are the best. I’ve tried lots of options, and these are the first pair I haven’t found a lingering critique of. The material is comfy and breathable, and they have a handy cargo pocket with a vertical zipper that can be easily accessed while sitting during a flight. I’ve seen plenty of folks fly in jeans, and have done so a few times myself, but pants with drawstring elasticized waistbands are a marked improvement for in-flight comfort.
If you’re committed to wearing something less athletic and more traditional-looking, 686’s Everywhere Pant is excellent. The material is durable, but still pretty comfortable, and the pants have enough pockets to put a fishing vest to shame. They also have drawstrings at the waist if you want to avoid wearing a belt – you should, belts are not your friend during air travel – that can be tied inside, or outside, of the waistband. If you are keen to pack minimally and want to wear one pair of pants in-flight and through your trip, the Everywhere Pant is the way to go. If you need a slightly more formal look, they come in a chino style that dresses up decently.
Last on the apparel list is footwear. Allbirds’ Tree Runners are my preferred sneakers for air travel – cliché, I know – as they are light, comfortable, and don’t take up much foot room. The latter is particularly important for me, as I have large feet (men’s 13), and at 6’4”, barely have leg and foot room during flights. I need my feet to fit around a bag under the seat in front of me, and bulky shoes don’t allow for that. I’m also a fan of visual minimalism with sneakers, and the monochromatic black Tree Runners don’t draw a lot of attention.
Usually, though, I prefer to wear flip flops during flights so my feet don’t feel constrained after a few hours. Indosoles’ slides are my favorites, because they vertically collapse so I can take my feet out of the shoe, but still rest them on top of the soles, and off the floor of the plane. They aren’t the most comfortable for longer walks, but if I have the Tree Runners in my carry-on, I just swap into them if I know I have to walk a ways through an airport.
Indosole flip flops and Blundstone 1901, both well worn.
Finally, get a pair of Blundstones. There’s no better shoe if your travel requires dressing up a bit, as well as walking through urban or natural environments. My favorites are the 1900 series dress chelseas, which, despite their name, can take a beating and still look good. As far as boots go, they are comfortable during flights because they don’t have the hotspots created by laces or cheaper construction techniques that leave rough internal seams.
Accessories/ Small Items
There’s a plethora of additional small items that can make travelling more comfortable. The items listed below are those that I consider essential, though they don’t represent the full complement of things I bring on board a plane.
Get a good water bottle, something metal, glass, or a combination of both. It’ll help keep water cool if you buy it, and let you take advantage of free filtered water in some airports. Just don’t get one with a straw, or at least not one that combines a no-leak seal and a straw. I did this once, and as soon as I opened the straw in the air, the pressure built up from the cabin pressure turned it into a rather majestic fountain that left me damp for a bit. Exciting, but not in a desired manner. Takeya has long made my favorite water bottle – it keeps water cold for a long time, is leak-free, and the sport cap lid makes it easy to access without worry of losing the bottle’s cap. The built-in grab handle also makes it easy to carry by hand or to clip to a bag.
It was only within the past year that I started using a seat cushion when flying longer distances, and the upgrade has made a world of difference. If you ever get off a flight feeling as if your tailbone, or any other part of you that contacts a seat, has been lit on fire, a good seat cushion will mitigate a lot of that discomfort. I’ve tried two options and found that the Everlasting Comfort memory foam cushion worked best. It has dense foam that doesn’t collapse after a couple of hours, and the rectangular shape fits within the bounds of a typical economy-class seat. It doesn’t have an in-built means of securing it when folded in half, but a dog collar does the job well. Credit to my wife and main travel partner for discovering the latter.
A good set of headphones, like a good seat cushion, can exponentially improve your travel experience. Noise-cancelling earbuds are great for flights under 7 hours, which is the upper range of battery life while using active-noise cancellation (ANC) for the best options. Jabra was my go-to, but the company recently announced that it will no longer produce headphones for casual use. I recently picked up Sony’s well-rated WF-1000XM5’s, which have great sound and ANC, if you can get the right fit with the OEM earbud tips. I’ve settled on Bose’s Quiet Comfort Earbuds, which sit better in my ears and have a comfortable fin that holds them in place. Their main drawback is an unnecessarily large case, but the tradeoff is worth it for their combination of sound quality and comfort.
If you are willing to spend big money on a high-quality pair of headphones, I recommend getting an over-the-ear pair, which has better sound quality, battery life, and offers greater comfort than earbuds. I’ve used a pair of Bose Quiet Comfort 45’s, and they are one of my most-prized pieces of travel gear.
When using wireless headphones on flights that have in-seat screens, you’ll need a connection method. Most over-the-ear headphones will include an auxiliary cable, but that means you are awkwardly tethered to the seat in front of you. I picked up the AirFly Pro 2 from Twelve South, which plugs into the in-seat unit and establishes a Bluetooth connection. If you plan to fly internationally, spend the extra $10 on the deluxe version, which includes a two-pronged plug that works with European carriers.
USB cables also come in handy, and plan to bring ones with both a USB-C and USB-A connection, as the latter is still the main charging port option on many planes. I’ve used this set from Iniu for years without fail, but this is a market saturated with quality, affordable options.
To help organize your electronics, including cables, find a small tech pouch. I’ve used the Alpaka Tech Case Mini, which is not currently in production, but there are lots of good options out there. Tomtoc effectively covers the budget end of the spectrum, while brands like Alpaka, Aer, Bellroy, Evergoods, and Peak Design make pricier, but higher-quality organizers.
For international travel, I advise getting a passport wallet. A good one won’t only protect your passport from damage, but also affords space to store boarding passes, baggage tracking tags, and some cash. You don’t have to spend a lot of money for effective quality, as I spent years using a basic passport wallet I picked up at Target 12+ years ago. Recently, I swung for a Bellroy Travel Wallet, which is expensive, but also very handy. It provides more storage than the more common portrait-oriented bifold passport wallets, yet is slimmer to carry. I wouldn’t recommend that you carry it while out in public at your destination, regardless of country, as it is still bulky enough to draw attention, but it is a great tool for getting through the entire air travel process.
Other Travel Tidbits
Some other tidbits of advice. The jetlag-mitigation practice that has worked best for me is to stay awake until normal sleeping hours upon reaching your destination. I once nearly fell asleep during dinner attempting this, but it helps to quickly get your mind and body in sync with the time change.
For US residents, if you have the means and qualify for the program, get Global Entry. TSA Pre-check is also useful, but Global Entry includes it, and adds in very useful benefits. A friend, while eating dinner in Nairobi, asked those of us at the table what possessions we value most. As Time Bum readers, you might assume I would’ve referenced a particular watch, but no, my answer was Global Entry, because of the accessibility and ease it provides. Freedom to move with relative ease is a significant privilege, increasingly so, and one that I’ve appreciated when returning to the US from abroad.
Download a translation tool on your phone for the local language(s) spoken at your destination, and test that it is working before you get there. I once had to use my extremely broken Spanish to convince a foreign border agent that a weighted blanket wasn’t, indeed, filled with illegal substances. The degree of difficulty in doing so would have been dramatically reduced had I ensured that the translation packet had properly downloaded before embarking on the trip.
Wait, What About Watches?
I’ve reviewed several GMT watches, automatic and quartz, all of which have their merits. I’ve even traveled overseas with a few of them, and found them to be great companions. After all that experience, what I’ve regularly turned to as an in-flight timekeeping tool is the humble Casio AE1200, known as the Royale or WorldTime. It has a number of handy functions, including easily adjustable dual time zone readouts, a chronograph, alarm, and a backlight that even the best painted lume can’t match. I’ve modded mine to get rid of the cheap plastic case in favor of a stainless replacement from SKXMods, which got rid of the watch’s only functional demerit. I also added one of Vario’s excellent fitted Cordura straps, which are comfortable, durable, and look great.
Yes, you can spend more on an analog GMT, and the horological gods know that I love a well-done analog GMT, but you don’t need to, from a functional perspective. For $100-$150, you can get a Royale and a mod kit, and have all your timekeeping needs satisfied.
Finally, the End!
There you have it, the inner workings of my mind, so far as air travel outfitting is concerned. Each of the market spaces I covered has a bevy of options I haven’t listed, and part of the joy of kitting out is rabbit-holing through each segment to find options to try out. You’ll get some things you decide aren’t right, but stay open to trial and error, and be honest with yourself about what you need, not what someone else tells you is the best item in a category. The idea is to curate a travel kit that enables you to enjoy traveling, not to show off to others.
