How To Pack 3 Weeks in a Carry-On (Like A Boss.)

May 30th 2014

Some years ago I flew from Chicago to London for an appearance on Top of the Pops. I was in a band that was sort of a big deal at the time. After dusting off from my long flight, I found that the airline had lost my bag. I had to make my first (and only) British television appearance in ill-fitting trousers borrowed from the record label representative. It wasn’t my finest moment.

Since then, I try never to check a bag if I can help it. Today I do a very different kind of traveling for work, but arriving at my destination with my belongings remains of utmost importance. And with today’s airline baggage fees, who can afford to check a bag anyway?

In 2012, after years of experience packing my life into a carry-on bag, I decided to share what I’ve learned with the world. My original post, How to Pack a Carry-On Like a Boss, went so viral that it remains the most highly trafficked post on my site today. And I’m a feminism blogger. Travel isn’t even my genre. But obviously I was on to something.

This summer I embark on a 24-day trip that combines planes, trains, and automobiles covering four different cities. Part of the trip is for work, and part is for a grad school internship. Needless today, I needed to carry a lot of things with me and some might assume there’s no way I could do it all in a carry-on. But I did. I am. And I’m here to show you how.

Let’s start with the size of the bag. I have here an airline-approved carry-on. It’s not an oversized suitcase that I’m calling a carry-on. This is the real deal.

Start by making sure that your clothes are organized and you know what you want to take. In 24 days, I AM going to have to do a load or two of laundry. I couldn’t go 24 days at home without doing laundry and it would be no different on the road. But I really despise laundry so I made sure that I only have to do it a maximum of 1-2 times. That’s all.

I took enough full outfits to get me through 12 days – that’s 6 dresses and 6 short/shirt combos. I also took 6 full workout outfits because I’m training for a 5k this summer, and of course I took shoes. So how do you get all this stuff in a carry-on with room to spare? Like this:

You start with a pillowcase. I love pillowcases because they’re light, roll easily, and can be used for a laundry bag after you unpack. Lay down the pillow case, neatly stack the clothes on top lengthwise, fold the pillowcase over, and roll tightly. You’ll end up with a little clothes burrito that takes up just a fraction of the space that folded clothes would.

Place that burrito in the bottom of the suitcase (the side that will be on the ground.) You’ll want to pack your heaviest rolls toward the bottom so the suitcase isn’t top-heavy.

Sort your clothes into as many rolls as you like. I like to organize my rolls by dresses, tops, skirts, fitness tops, fitness bottoms, etc.

Arrange all the rolls neatly next to each other in whatever configuration works with the size burritos you’re making.

Next, you’ll need your toiletries. Obviously for three weeks, trial size isn’t going to be enough, but I pack a TSA-approved set to get me there, which I’ll have to replenish at some point.

Here’s my time-saving tip to you – ALWAYS pack your toiletries in the outside pocket of your carry-on for easy access at security. You do not want to have to open a carry-on to dig something out when you’re standing in that long security line.

Last, I packed my undergarments, belts, scarves, accessories, etc into the pockets on the inside flap. I also packed my running shoes, some pretty Toms, and some flip flips.

And after all that, this is my final packed product. The contents listed are exactly what is packed in this bag. I could take nothing else but a wallet and be set for my trip.

And just to prove to you that it’s really a carry-on, that’s me, five-and-a-half-feet tall, standing next to it. See!

Most people ask if I took any other bag beside this and yes, I took my backpack for my laptop, iPad, wallet, etc. Most airlines will let you bring a free carry-on and a free personal item such as a backpack, purse, laptop bag, etc.

Now, go forth, roll your clothes burritos, and save your family from hefty checked bag fees!


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5 Responses to “How To Pack 3 Weeks in a Carry-On (Like A Boss.)”

  1. VN:R_U [1.9.22_1171]
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    Great tutorial, as always! :-)

  2. VN:R_U [1.9.22_1171]
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    Can you come pack my luggage? Also, just so you know, you’re on Thought Cataloge just now

  3. VN:R_U [1.9.22_1171]
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    I just had a business conference in Vegas and was gone for 6 days. I totally used your previous tutorial and packed LIKE A BOSS!!
    I not only needed to have business and casual but some evening wear as well. I managed to get it all, plus 4 pairs of shoes, ALL my toiletries (which is a lot) and accessories!
    On the flight back, I used a large shopping bag to pack everything I’d accumulated, gifts, souvenirs, some food for the flight and had my purse as well. I had no issues carrying on slightly more items and made it through my trip without losing a single thing!!

  4. VN:R_U [1.9.22_1171]
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    We are flying Spirit tomorrow and you can’t even fly with a carry on without paying in that airline! If they weren’t the cheapest for tickets to our destination, I do t think I would have chosen them. I’m definitely going to try this when packing our suitcases today, though!!!

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