How To Send Yourself Packing

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Packing in a few trips is one of my favorite things to do in summer. You know what’s not so great? Tripping over packing. You know the story: we end up waiting until the last minute, over-packing, under-packing, and no matter how hard we try, we forgo the carry-on and condemn ourselves to baggage fees and long waits by the seemingly perpetually-motionless baggage carousel. It’s a disaster.

There has to be a better way! And there is! I hate to sound like your mother but the best way to avoid luggage issues is to avoid them by packing smarter, and smaller…like this:


You’re going to be gone for five days, do you really need to bring four different pairs of shoes? Unless you’re doing a bunch of red carpet appearances for your upcoming summer blockbuster, the answer is no.

Like we spoke about with food, the key to keeping things manageable is to plan ahead. For a five day trip you’ll need:
Five pairs of socks and underwear (plus one extra, just in case. See mom, I listened when I was a kid)
Five shirts, and
Two or three pairs of pants and shorts/dresses and skirts
A few pairs of shoes.

If you’re going to a beach, or plan to live by the pool, replace a pair of the pants/skirts with a bathing suit and you, my friend, are set with clothing.


Just because we have everything we’re bringing with us, doesn’t mean the challenge is over. Remember, the goal here is to pack as efficiently as possible so we don’t have to check bags, maybe ever.

When it comes to packing clothes, the common refrain is to fold, place, repeat. However, depending on your folding style, this may take up more room than necessary. That’s why I like to add one extra step after I’ve finished folding an article of clothing: rolling it into a tube shape. Granted, this doesn’t really apply to fancy clothes, but if you’re going on vacation, the chances are you’re not trying to bring a suit bag.


Fold these in the usual way – you know, sleeves in, and once in half – and then roll up from the bottom. This reduces the “spatial footprint” (I hate myself for saying that) of the shirt in your bag, allowing you to fit more. Do this with every shirt and sequester them to one side/corner of your bag so you’ll know where to find them.


Same idea as the shirts, really. Fold these bad boys in half and roll down from the top. Find another area in your bag to put them and voila! You’re halfway home and already there is so much more space in your bag, isn’t there?


These are tiny to begin with so your folding style doesn’t make much of a difference. Fold your underwear however your heart desires and put them in one of the two remaining empty corners of your bag.

The socks on the other hand get a special place. Instead of just placing your socks in your bag, take the ball of sock that you have created and stick them in your shoes. It takes up less space, and keeps all feet-related items together.

(Tip: You can do the same thing with your belts and chargers. No more worrying about misplacing or tangling them. Nothing gets tangled up in … shoes)


Choose one of the remaining empty corners in your bag, place your shoes like this, and put them there. Packing your shoes like this also gives you the ability to stack more than one pair vertically.


This is the most important aspect of packing because there are actual rules governing what you can and cannot fly with. Make sure all of your liquids and gels are in containers that hold no more than three ounces, and make them easily accessible.

If you do not want to check your bags (of course you don’t), or throw away some of your stuff at the airport (again, duh), leave the razors, large toothpastes, lotions, and anything that’s not essential, at home.


Don’t go out and buy a new bag, but make sure it’s not too big to fit in the overhead compartment. Small duffel bags and backpacks work best, but those tiny roller bags work just as well.

Until next time – stow your tray table and prepare for takeoff.

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When Arye isn't helping optimize your time, he is doing his part to ensure life is full of shenanigans.