How to Pack for a Trip (yes, there’s a right way to do it)

Shawn Forno

Contrary to popular opinion, there actually is a “right way to pack.” In fact, there are dozens of right ways to pack. It just depends on how you travel. Rolling vs. folding, compression bags vs. packing cubes, Marie Kondo “KonMari” minimalism vs. Guy Fieri excess—they each have a place in your packing strategy. The trick is to know how to use them.

Each specific trip, destination, mode of travel, duration, season, mobility, work requirements, budget, style, wardrobe, commitments, and pace all help determine the right way to pack. Every traveler is different and every trip is special, but the secret to packing like a black belt travel ninja is to mash up the best parts of each packing plan into a carry on Frankenstein that works for you.

Here are my favorite packing tips, tricks, techniques, and takeaways for packing “the right way” for just about any trip in this big, wide world.

The Right Way to Pack

If I could only ask you one question about your trip before I packed your bag it would be: How often are you going to repack your bag on this trip? How often you’re on the move single-handedly determines how you should pack. End of discussion.

If you’re a digital nomad setting up camp in an apartment for two months, you’re going to pack differently than a college kid bouncing from hostel to hostel every night. Portability and organization are keys to your packing strategy if you’re on the move, but maximizing space with compact tetris-like precision is the name of the game for those sedentary long-haul packers.

Packing On the Go: Packing Cubes

If you’re going to be repacking your backpack every single day, packing cubes—and the discipline to use them—are a must. Commit to one large packing cube for your shirts (this will also limit how many Blink 182 t-shirts you can bring), and roll your cotton and polyester shirts into each one. Packing cubes work best with rolled clothes (you can stuff each item into a smaller space and keep them organized at the same time).

Packing well is all about staying organized. If you dump your backpack out every night to get your toothbrush and phone charger, that’s not actually packing. That’s just carrying a heavy backpack shaped garbage sack. Your backpack should help you enjoy the trip by making it easy to see each new destination with the right gear and zero hassle.

A single large packing cube for cotton shirts and a smaller packing cube for underwear and socks will keep you

organizedand ready to repack at a moment’s notice—even when you’re super hungover from the night before. However, packing cubes aren’t great for every item of clothing.

KonMari Packing

Rolling up your jeans and heavy sweaters is a waste of space, even if you stuff them in a packing cube. You’ve just taken up a lot of space and not really gotten organized. Cubes are great for small, homogenous items (shirts, shorts, underwear). Bulkier items can stand alone in your bag, as long as they’re folded neatly.

“Soft, wrinkle-resistant materials like knits, wool, and cotton can all be rolled without much worry—just make sure you keep the roll tight, since loose rolling will result in wrinkles, regardless of the material. Starched garments like collared shirts and dressier items should always be folded. The combo should be enough to let you cram everything in without looking like a mess at your destination.” – Andrew Tarantola, Gizmodo

Embrace the KonMari folding method and vertically store your pants and bigger items so you can see everything at a glance when you open your bag, while still keeping it all tidy. It’s the best of both worlds.

You can even fold sweaters like this:

If you’re really trying to look sharp, but you’re on the move either get a wrinkle-resistant shirt or learn the folding origami magic of double folding your shirts a la, Louis Vuitton.

When you fold button up shirts together, the interstitial suspension (yes, there’s physics involved in next level packing tips) keeps the shirts from wrinkling. It also helps if you fold the collars down flat. Alternatively, you can keep your collars wrinkle free by stuffing a belt in the collar to reinforce it, but honestly, I’d rather wear my belt to keep my pants up. But hey, that’s just me.

However you decide to flash travel, packing cubes are travel legos, and they’re a lifesaver if you’re always repacking your bag. Just don’t try to cram everything into packing cubes. A neat crisp fold is sometimes your best bet.

Budget Packing Cube Option: Ten gallon Ziploc freezer bags. Just make sure to get the kind that zip shut. They’re easier to use.

The Importance of a Good Daypack

I always stress the importance of a daypack when you travel, but more important than a great daypack, is room in your main bag for a daypack. Do not become one of those people that straps an additional bulging day pack to their chest while they carry their “carry on” backpack on their back.

It defeats the whole reason for traveling light when you add more bags to the equation. If you’re only traveling for a few days or weeks, keep everything in your main bag—including any additional stuff sacks, tote bags, or daypacks. You’ll be glad you did, because when you get to your destination, you can just pop open your bag, pack a few items and hit the road without reshuffling all your stuff.

The Smallest Bathroom Bag

Packing your bathroom bag is about more than just buying travel-sized toiletries, it’s about packing a travel sized bag. I’ve seen bulging bathroom bags that take up half a carry on backpack. Honestly, if you can’t get your bathroom bag down to a handful of items, then carry on packing might not be for you.

A lot of flexibility and room in your bag is lost when you bring shampoo, soap, body wash, shaving cream, an electric razor, toothbrush, toothpaste, floss, mouthwash, makeup remover, Q-tips, cologne, lotion, body lotion, body butter, and beard oil. You just can’t bring all that crap in a carry on bag.

Pro Tip: Bring a roll of medical or electrical tape. It’s super useful as a waterproof(ish) band-aid and just a general all-purpose fix-it… thing. I use it every time I travel to fix something. Usually me.

Packing for a Long Stay

All the rules change when you’re packing for the long haul. Now it becomes about getting the max amount of (useful) stuff in your bag so you can land and get to work settling into your surroundings without wasting time getting set up. This includes some complicated folding strategies, and isn’t about the functionality and flow of cute packing methods like packing cubes and KonMari folding.

Long haul packing is about getting everything in that bag and getting the zipper closed.

Compression Bags Rule

The right compression bag can save you time and money by letting you cram those last few essentials in your bag before the big move. I don’t advocate bringing more than you need, but a long trip is different than an eight day getaway. I was in Iceland for two months, and I was pumped I didn’t have to spend hundreds of dollars on winter clothing when I landed. Spoiler alert: Iceland is super expensive.

The best way to use a compression sack is to flat fold your knits and woolen clothing and compress away. Jeans and most pants aren’t worth the effort.

The Eagle Creek Compression Bag comes in a few sizes and won’t break the bank. But better yet, you don’t need a vacuum or weird attachment to use it. Just compress the air out, zip it shut, and blammo. You saved some space for all your sweet tees.

Honestly, other than that, you can bundle pack your gear by wrapping it all in a matryoshka doll of folds and layers, but I don’t think you have to get that extreme. Just pack enough clothing for 2 weeks, and wash rinse, repeat. Everything else is bonus material.

Once you do actually get where you’re going, embrace the KonMari folding method in your drawers. It’s surprisingly easy to do, and you’ll appreciate the simplicity and sleek functionality of being able to see all your options in a glance without digging around. Seriously. Game changer.

Things You Should Always Pack, No Matter What

Always Bring a Swimsuit

I don’t care where you’re going or why you’re there. Work retreat in Uzbekistan? Bring a swimsuit. Mission to Mars—swimsuit. Bathing suits take up very little space yet do so dang much. They’re perfect for swimming (obvi), great for sleeping in when you share a room (or a dorm) with a lot of people, and they often double as a pair of shorts or a sports bra for a day trip, hike, or jaunt around town—especially if you get a stylish pair of hybrid shorts.

A swimsuit is worth its weight in gold, and you should always pack one.

An Extra Pair of Lightweight Shoes

I used to bring only one pair of shoes for any trip—the shoes on my feet. But now, in my old age, I’ve realized that a pair of espadrilles (Toms) are a nice luxury for just about any trip. They don’t have laces (sweet for airport security), they’re comfy, and they take up very little space in my bag. Heck, you can even pack them in most stuff slots on the side of your pack. Just make sure they don’t fall out.

Eye Mask for the Win

When you travel, you’re gonna be… traveling. That means long bus rides, packed flights, and crowded well lit hostels, or even hotel rooms. I once had a bright EXIT sign in my hotel room. All night. That green neon is burned into my retinas.

A simple, comfy lightweight eye mask will be your salvation when you really just need some shuteye. Pack it. You’re welcome. REI makes a great padded eye mask with a little pocket above the bridge of your nose for storing ear plugs or even a sleeping pill for those really restless nights.

Pro Tip: Throw away the ear plugs that come with mask and buy a cheap pair of foam ones.

Invest in Quality Gear

Merino wool travel shirts. Merino wool socks. Quality approach hiking shoes. A rain jacket that can take a beating and fold down to the size of a napkin. Being able to afford nice gear is a privilege, but it really does make packing for any trip easier when you invest in a few pieces of quality gear that can go the distance.

Ironically, quality high-price gear often ends up paying for itself over the years, due to the fact that you don’t have to replace it. But if you can’t afford the latest and greatest, read the reviews and find a few pieces (used) that work for you. If the owners are willing to sell.

Quality gear packs better, weighs less, wears better, and lasts longer. Get it if you can.

Stuff to Leave Behind

  • Liquid Sunscreen – Buy it when you get there. Then use it. All of it.
  • Big Ass Coat – You just don’t need a massive travel jacket. Get a small one and treat it like a day bag for city travel and flights.
  • That Third Pair of Shoes – Two is plenty.
  • Hair dryer – Stop it.
  • Travel umbrella – HAHAHAHAHAHA
  • Everything else you think you need “just in case.”

Travel is about those “just in case” moments. If you insulate yourself from them, you miss out on the whole point of travel.


Carry on packing is like jazz—it’s about the notes you don’t play. You’ve heard it before, but less really is more. When you pack poorly, you pay the price—sometimes literally. Overage baggage fees, lost luggage, wasted time looking for your stuff, and packing and unpacking bulging bags every time you need to get your toothbrush.

Don’t just commit to packing in a carry on bag. Learn how to create a better destination specific packing list, bring the things you actually need for your trip (not anything extra), and maximize the space in your backpack for all your essentials.

  • Roll cotton clothing, thin wool, and knits; fold everything else
  • Embrace the magic of KonMari folding; it’s fire
  • Compression bags are awesome for slow, long haul travel
  • Keep your toiletries in a separate compartment; seriously

Want more like this?

Get weekly gear reviews, travel hacks, and packing tips sent straight to your inbox. As an added bonus, we’ll send you a carry on packing list right away.