I’ve typically flown 50ish times a year for the past 3 years. This past year, I set a personal record by spending 11 months living out of a suitcase, compared to the 4-5 months I typically average. I’m taking a short breawk at home right now and I’ll be living another year out of a suitcase soon. As a self-proclaimed gear geek, I enjoy researching and purchasing high-quality equipment for all my hobbies, including travel. Like equipment in an RPG, there’s a limit to how much we can carry while being practical, thus the “best in slot” concept. Over time, I’ve tried numerous travel gear combinations and formed my own opinions on them. While my setup might not work for everyone, I hope it offers some useful insights and things to consider.

Travel Constraints

There are a few key factors that shape the gear I carry:

  1. Diverse Climates: I often travel across varying climates without returning home. This means I always need to pack both beachwear and winter gear.

  2. Formal Venues: Whether it’s a private club, a ball, or an upscale restaurant, I often visit places with dress codes.

  3. Accommodations: I don’t always stay in the same level of accommodation, it may be a 5 star hotel one week and a hostel the next, or even the hotel floor if I’m unlucky.

Bags and Containers

I travel with four basic carrying bags: a check-in bag, a backpack, a packable backpack, and a crossbody bag.

  • Check-in Bag: The Osprey Farpoint 65L Wheeled Travel Pack is my go-to. It’s smaller than most check-in bags but has a big advantage: it can transform into a suspended backpack. I mainly roll it, but the backpack feature comes in handy on public transit with lots of stairs and steep cities. If you’re carrying makeup kits or bulkier items, this bag might be too compact. I hate that it only has two wheels though, I wish I could roll it upright with four.

  • Backpack: My backpack is the SOC Three Day Pass, a reliable military bag that I’ve used from boot camp to deployments. I got my first one when I joined the military and it went around the world with me. A decade later, the bag was so worn it looked like a towel when I hung it. It was used well beyond what one would consider reasonable wear but they honored their lifetime warranty and sent me a new one. It’s great for expanding when I need more space, and I always carry some airport essentials in it: an emergency foil blanket and a Matador Large NanoDry Packable Shower Towel.

  • Packable Backpack: I use the Herschel Packable Daypack when I don’t want to carry a full backpack but still need a handy bag for souvenirs or extra items. It’s waterproof and fits in my pocket.

  • Crossbody Bag: I use a Rimowa Crossbody Bag when I need easy access to my wallet, AirPods, charger, sunglasses, and coins, especially in places like Europe or Japan where coins are valuable. It’s stylish and the Rimowa brand sells the lifestyle I want to embody.

Packing Cubes

While there’s debate on their effectiveness, I find packing cubes help keep things organized and compressed. I use Thule cubes for clean clothes and REI cubes for dirty laundry. The Thule cubes compress well, while the REI cubes allow airflow to prevent odors. Don’t forget a toiletry bag! I recommend a mesh one for easy access, especially at airports with liquid regulations.

Clothing

  • Shirts: I pack six merino wool T-shirts and one polo, which work in various climates and are odor-resistant. This is probably the most efficient route but I’m starting to just perfer wearing shirts that I like for some wardrobe variety. For more formal occasions, I bring two non-iron button-down shirts (Brooks Brothers and Lululemon), which I pack in a garment folder immediately out of a drier to minimize wrinkles (non-iron is a blatant lie).

  • Pants: I carry three pairs of pants: jeans (Levi’s Japanese Selvedge 514s), Lululemon hiking pants (merino wool), and formal pants (Lululemon Commission Pants).

  • Jackets: My outer layer is a Burberry Short Trench Coat, which is durable enough for hikes and stylish enough for dinners. For colder climates, I’ll use the liner. Lastly is a Nike Elements Half-Zip top; I wear this on planes and when it’s colder than room temperature outside.

  • Shoes: My everyday shoes are Gore-Tex Converse Chuck 70s, good for rainy and snowy weather. For formal events, I have Gucci Horsebit Loafers, which can double as slippers. I also carry black sandals for the beach.

  • Socks: I bring seven pairs of merino wool Darn Tough Socks, which are durable and come with a lifetime warranty.

Electronics

I’ve experimented with travel setups for my tech, and I currently use the Omen Transcend 14 for gaming and work on the go. Though it has some software quirks, it offers the best compromise for my needs. I also carry a wireless Xtrfy M42 mouse, SteelSeries QcK Medium mousepad, AirPods for noise cancellation, MagSafe battery packs, a flash drive, and the MOGICS Super Bagel Adapter.

Travel Gear

The SecretLabs travel pillow is like a soft neck brace with a satisfyingly tactile magnetic latch. I also carry a Victorinox Cybertool for unexpected needs. Lastly I tag my luggage with integrated AirTags for tracking.

Considerations

Here’s a breakdown of some items I’ve spent time debating and how I ultimately decided what worked best for me.

Packing Cubes?

There’s some debate on whether packing cubes actually help since they leave space in the luggage if they don’t fit perfectly, which is especially true in my oddly shaped carry on. Packing cubes do help because a large pile of clothes is harder to compress all at once than compressing individual cubes of clothes. Then if you’re so inclined to make the most out of your space, you can stuff socks, underwear, and pajamas into the crevices not filled by the cubes in your luggage. I use packing cubes from Thule for my clean clothes and packing cubes from REI for my dirty clothes. The main difference is the Thule ones compress really well and the REI ones have mesh so your dirty clothes don’t get super dank.

Travel Shoes?

I initially used Pampa Palladium Travel Lite+ Waterproof shoes, which were easy to slip on and off, provided waterproof protection, and offered durability. With a history rooted in military design, they were ideal for rugged wear and comfort—after adding more supportive insoles. The only drawback was their appearance; they look distinctly like hiking shoes, especially with their elastic laces, making them harder to style with outfits outside of hiking attire. Eventually, I transitioned to Gore-Tex Converse Chuck 70s for a sleeker look that still handles rain and snow, combining style with function for urban exploring.

Puffy Jackets?

For years, I traveled with a North Face Nuptse puffy jacket, which was lightweight, packable, and incredibly insulating in colder weather. The problem was its maintenance: puffy jackets typically require special detergent to care for the down. Although they’re compact and effective, I ultimately decided against bringing the Nuptse for super extended trips.

Computer?

Traveling with a laptop is often a necessary compromise, but I’ve struggled with it for years. This might sound ridiculous, but for me, home is where my desktop computer is, so bringing something like it along is very important for me to feel comfortable. I experimented with a Windows Surface Pro tablet combined with a mechanical keyboard and mouse. I even tried traveling with a compact ITX PC paired with a portable monitor for an extended trip. Now, I use the Omen Transcend 14. While I still compromise by not carrying a separate keyboard, I do pack a mouse and a SteelSeries QcK Medium Mousepad, advertised as a “Low Profile Mousepad with Easy Travel Surface”.


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