I used to be that guy at the gate.
You know the one — frantically rearranging his bag on the floor while everyone else is calmly boarding.
Shoes half out, toiletry bag exploding, laptop somehow buried under three layers of “just in case” clothing.
It was embarrassing, honestly.
But after a solid stretch of back-to-back trips — weekend getaways, long-hauls, layovers that stretched into small eternities — I finally cracked the code.
I figured out exactly what goes in my carry on, exactly how it goes in, and exactly what I was wasting space on for years.
This is that list.
My First Rule: The Bag Itself Has to Be Right
Before I even talk about what goes in the bag, we have to talk about the bag.
Because I spent way too long stuffing things into a carry on that was technically the right size but practically a nightmare to live out of.
The sweet spot for me is a 40L bag — structured enough to stand on its own, but soft enough to squeeze into an overhead bin without a fight.
I personally can’t go back to hard-shell carry ons for shorter trips.
They feel rigid and unforgiving when you’re just trying to jam one last hoodie in.
A good carry on should have a dedicated laptop sleeve, an exterior pocket you can actually reach at security, and some kind of internal organization — whether that’s built-in pockets or just enough open space to use packing cubes your way.
If I had to start over today, I’d prioritize that exterior pocket above everything else.
Being able to grab your passport and boarding pass without opening the whole bag?
That alone reduces airport stress by about fifty percent.
Not exaggerating.
Tap to Explore These Beauties
See my ideas in action 👇 Tap any image to explore full details.
Packing Cubes Changed My Life (I Know Everyone Says That, But Hear Me Out)
I resisted packing cubes for years.
Thought they were one of those travel gadget things people buy and never use.
Then a buddy of mine showed me how he packed for a two-week trip to Southeast Asia in a single carry on using three packing cubes.
I was converted on the spot.
The way I run it now: one cube for tops, one for bottoms, one for everything else — socks, underwear, workout gear.
The compression ones are great if you’re packing bulkier items or a lot of layers.
For warm weather trips, the regular slim cubes are honestly enough.
What I love about them is you stop digging.
You never open your whole bag just to find one shirt.
You just pull out the right cube, grab what you need, and put it back.
It sounds like a small thing but when you’re in a hostel dorm at 6am or a dark hotel room trying not to wake your travel partner, you’ll thank yourself.
And here’s a little tip I don’t see people mention enough — pack the cubes vertically in your bag, not flat.
You can see everything at once.
It’s a total shift.
The Clothing Formula I Actually Use
Okay, this is the core of the whole operation.
I use what I call the 3-2-1 rule, loosely.
Three tops, two bottoms, one layer.
That’s the foundation for a trip up to five or six days.
Now, the tops need to be versatile.
I’m not throwing in anything with a loud print or something that only works with one specific outfit.
Everything should mix and match.
A neutral tee, a slightly dressier button-down that can go casual or pulled-together, and one more depending on the weather.
For bottoms, a solid pair of dark jeans that can do double duty from the plane to a nice dinner is my ride-or-die.
Add one more bottom — shorts, chinos, whatever fits the destination.
The one layer is usually a lightweight bomber or a packable fleece.
Something that compresses small but actually keeps you warm on a chilly flight.
I wear the bulkiest items on travel day.
Always.
Heavier shoes on my feet, the jacket on my back.
That alone frees up a ridiculous amount of space in the bag.
🗼 I Wrote a Book About My Japan Travel Catastrophes!
Before I landed in Tokyo, I thought I was the “Final Boss” of international travel. Spoiler alert: I WASN’T. 😅
🚅 I boarded the wrong Shinkansen and ended up in THE WRONG CITY. I confused locals with my “expert” bowing that was more awkward than accurate. I accidentally stumbled into a high-stakes Kendo practice thinking it was a tourist show. Sound like something you’d do?
“Things I Wish I Knew Before Going to Japan” is your shortcut to avoiding ALL my cringe-worthy mistakes. ✨ Inside, you’ll find practical, LIFE-SAVING tips on etiquette, transport, money, and hidden gems that will save you time, money, and a whole lot of confusion.
Shoes: The Eternal Carry On Struggle
Shoes are the carry on killer.
They eat space, they’re awkward shapes, and everyone over-packs them.
My honest rule is two pairs max when I’m carry on only.
Whatever I’m wearing on the plane — usually a clean sneaker that can handle walking and a decent dinner — counts as pair one.
Pair two goes in the bag.
For warmer trips that’s usually a sandal or a slip-on.
For colder trips it might be a lightweight boot that I can dress up or down.
The trick with shoes in the bag is to stuff them.
Socks, small items, anything that would otherwise take up space — shove it inside the shoes.
It sounds obvious but a lot of people just toss shoes in empty and lose that cavity space entirely.
I also wrap shoes in a shower cap or a dust bag if I have one.
Keeps everything else clean and you’re not hunting for a bag when you get to the hotel.
Three pairs of shoes for a carry on trip is almost always overkill.
Trust yourself on this one.
Toiletries: The 3-1-1 Bag Done Right
Airport security and toiletries have a complicated relationship.
The 3-1-1 rule is real — liquids in containers 3.4 oz or under, all in one clear quart-sized bag.
And honestly, once you build a dedicated toiletry kit that lives in your carry on, it becomes automatic.
My permanent kit has: toothbrush, toothpaste (travel size), deodorant, face wash, moisturizer with SPF, a small cologne sample, lip balm, and a razor.
That’s it for the everyday stuff.
Everything is travel-sized or decanted into small reusable bottles.
Those little refillable silicone bottles are genuinely one of the better travel investments I’ve made.
A few drops of your shampoo, conditioner, whatever — fill it up, label it with a piece of tape, done.
I also keep a small first aid card in the toiletry bag — a couple of ibuprofen, a bandage, some Pepto tablets.
Not a full pharmacy.
Just enough that you’re not the guy hunting down a drugstore at 11pm in a foreign city because you got a blister.
Been that guy.
It’s not a fun night.
The Tech Setup That Doesn’t Slow Me Down
I travel with technology, but I try to be intentional about it.
My carry on tech list: laptop, phone charger with a multi-port USB adapter, a power bank, earbuds or noise-canceling headphones, and a universal travel adapter if I’m going international.
That’s the core four, five really.
Everything goes into a small tech pouch that sits in my bag’s laptop compartment or exterior pocket.
No tangled cables floating around the main compartment.
Cords stay wrapped with velcro ties — the little reusable ones.
I know some guys travel lighter and skip the laptop entirely if they’re on a pure vacation.
That’s valid.
But if there’s any chance I’ll need to work or the trip stretches longer, the laptop comes.
One thing I added recently that I didn’t expect to use as much as I do — a small tablet stand that folds flat.
On long flights, propping up something to watch instead of holding your phone the whole time is genuinely comfortable.
Small, lightweight, fits flat in the bag.
Worth it.
Sleep and Comfort Items (The Underrated Ones)
Long flights without a few comfort items are a kind of suffering.
I don’t travel with a full neck pillow anymore — those big U-shaped ones take up too much room and honestly never worked great for me anyway.
But I do pack a few things that make a real difference.
A lightweight sleep mask is number one.
Doesn’t take up any space, folds flat, and the difference between sleeping on a red-eye and not sleeping on a red-eye is pretty much directly tied to whether the light is blocked out.
A pair of compression socks is another one I started doing a few years back and never stopped.
Your legs just feel better when you land.
I also always throw in a small travel blanket scarf — one of those lightweight ones that doubles as a wrap.
Airlines can be freezing or perfectly comfortable, there’s no predicting it.
And having something warm that doesn’t take up a shoe-sized chunk of your bag is a small win you’ll appreciate at 30,000 feet.
Documents and Essentials: The “Don’t Lose This” Section
This section of my carry on is non-negotiable.
Passport, ID, travel insurance info, a small amount of local currency if I’m going international — all of it goes in one dedicated spot.
I use a slim travel wallet for this.
Not one of those giant accordion folders that looks like you’re filing taxes at the airport.
Just a slim passport holder that fits in my jacket pocket or the very top of my bag.
I always make a photo copy of my passport and save it in my phone’s photos and email it to myself.
Sounds paranoid until the one time something goes wrong.
I also keep a physical backup credit card separate from my main wallet.
In a different zipper pocket.
If your wallet gets lost or stolen on a trip, having a backup card tucked away in your bag means you can still eat, still get a room, still function.
These aren’t things you want to be figuring out in the moment.
Build the system once, keep it consistent, and it just runs quietly in the background every trip.
Snacks: Yes, This Is Carry On Essential Territory
I’m putting snacks on this list and I’m not apologizing for it.
Airport food is expensive, often not that great, and sometimes the flight is long enough that what they serve doesn’t line up with when you’re actually hungry.
My go-to carry on snacks: a couple of protein bars, some mixed nuts, maybe a piece of fruit if I grabbed one before security.
Nothing that’s going to smell up the whole cabin.
Nothing sticky or messy.
Just a small zip bag of things that will keep me from being “that guy” staring blankly at the $18 sandwich at the gate.
If I’m connecting internationally, I make sure I finish or toss fresh fruit before landing — customs can be strict about that and it’s not worth the hassle.
Hydration is big too.
I always carry an empty water bottle through security and fill it up at the fountain on the other side.
Staying hydrated on a flight genuinely affects how you feel when you land.
It’s one of those unsexy travel tips that’s just… true.
🗼 I Wrote a Book About My Japan Travel Catastrophes!
Before I landed in Tokyo, I thought I was the “Final Boss” of international travel. Spoiler alert: I WASN’T. 😅
🚅 I boarded the wrong Shinkansen and ended up in THE WRONG CITY. I confused locals with my “expert” bowing that was more awkward than accurate. I accidentally stumbled into a high-stakes Kendo practice thinking it was a tourist show. Sound like something you’d do?
“Things I Wish I Knew Before Going to Japan” is your shortcut to avoiding ALL my cringe-worthy mistakes. ✨ Inside, you’ll find practical, LIFE-SAVING tips on etiquette, transport, money, and hidden gems that will save you time, money, and a whole lot of confusion.
What I Always Leave Out (The Stuff That Wastes Space)
Packing light is as much about what you don’t bring as what you do.
Here’s my personal cut list — things I used to pack and now never do.
A full-size towel.
Hotels and Airbnbs almost always have them, and the times they don’t, a quick microfiber travel towel is thirty times smaller and dries faster anyway.
Multiple pairs of jeans.
One good pair does the work.
Jeans are heavy, they take forever to dry if you hand wash them, and they take up a disproportionate amount of your bag.
A “just in case” outfit for some event that probably won’t happen.
I’ve packed formal event backup clothes exactly zero times that actually got used.
Every time I left them home I was fine.
A full book.
I know.
But I read on my phone or tablet now.
A paperback sounds romantic until you’re weighing every ounce and need the space.
Every item you pull out of the “just in case” pile before a trip is a small victory.
Learn to trust yourself.
My Carry On Routine the Night Before
The actual packing is one part of this.
The night-before routine is what makes everything click.
I lay everything out on the bed first.
All of it.
Every item I’m thinking about taking — flat on the comforter so I can see it all at once.
Then I do a pass and ask: do I actually need this?
Would I miss it if I left it?
Can something else do double duty?
After that pass, I pack the cubes.
Then I pack the bag in a specific order: cubes go in first, tech pouch next, shoes on the side, toiletry bag on top where it’s easy to grab for security.
Jacket, snacks, and any loose items get sorted last.
My bag is always ready the night before.
Never the morning of.
Morning-of packing is where you make bad decisions and throw in things you don’t need because your brain is in chaos mode.
Night-before packing is calm, deliberate, and you’ll sleep knowing you’re sorted.
The One Item That Surprised Me Most
If someone had told me earlier that a lightweight packable daypack would become one of my most-used travel items, I probably would have shrugged.
But here we are.
I fold a small daypack — one that compresses down to the size of a softball — into the outer pocket of my carry on on every trip.
And then I use it constantly.
Day hikes, city walking days, beach days, carrying things home from a market — the daypack absorbs whatever the day throws at me without me needing to haul my full carry on around.
It’s also a lifesaver for layovers where you want to move around the airport without dragging everything.
The best ones weigh almost nothing and hold more than you expect.
Mesh side pockets, a basic zip top, a back panel that’s comfortable against your shoulders.
That’s really all you need.
Mine is a solid dark navy color — goes with everything, doesn’t show dirt, doesn’t scream “tourist.”
It’s the kind of item that quietly earns its spot in your bag on every single trip, and you only notice how much you rely on it when you forget it.
