

True life: I’m addicted to saving money.
I know you’d think I wasn’t, considering how much I travel – along with my love for rooftop cocktails and brunch. But I swear it’s true!
If there’s a discount, I’ll find it. If there’s a coupon, I’ll clip it out. If there’s a rewards program, best BELIEVE I’m already a member! And if there’s a flight? I’m not paying for me AND my bags to get there. That’s why when I packed for a 10-day trip in Cuba (20 outfits), with the commentary of my doubting friends and family, I was able to simply take a carry-on suitcase and a personal item. No bags checked, and 30 more dollars to put toward something more interesting than luggage.
It’s not all about being cheap though, it’s also my raging paranoia that the airline is going to lose my suitcase. I’ve heard horror stories of trips gone sour because luggage has been lost in a Bermuda Triangle of suitcases, to maybe (or maybe not) be seen ever again.
Plus, you have more room to arrive to the airport at a later time when you’re not checking bags. Hello, beauty sleep (and a couple more glasses of wine before bed).
You might assume the answer is to pack light, but coming from someone who needs two outfits per day minimum, there’s no way. Now that you know why, you’re probably wondering how a woman with a million things can pack her entire life into two small bags. If I can do it, you can too – and only with five tidbits of advice. #TeamCarryOn
Table of Contents
1. Your New Besties: A Hard-Shell Carry-On and a Small Duffel
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Before we get to the real magic, you absolutely need the right luggage to make this work. I don’t want any DMs about this not working for you until you get the right luggage!
Kidding. But not really.
It’s necessary to use a hard-shell suitcase instead of a canvas one, as the two sides allow for more organization and for more items to fit properly because of its structure. As always, be sure to check the airline’s regulations on the size of carry-ons they allow. It’s typically the same across the board, with 22″ x 14″ x 9″ being most common. Most carry-ons will be labeled as approved when you purchase them.
Here are my picks!
Instagram Worthy: Betsey Johnson (Comes in several designs!)
Next comes our space saver: the personal item. While the carry-on suitcase goes into an overhead bin on an aircraft, your personal item must fit underneath the seat in front of you to avoid incurring additional fees. Remember to check the airline’s regulations for the size of this bag as well – it’s typically 18″ x 14″ x 8″.
While my Nike duffel has become my weapon of choice lately, let me make some versatile recommendations.
Okay, you’ve got your luggage. So now what?
2. Use a Packing List
One way I ensure that I don’t forget any items is to always use a packing list. Not only will it ensure that you remember everything you need, but it’ll also help you to cut down on any unnecessary items. Only bring what you know you’ll need for the most part! We’ve all been on a trip where it feels like our suitcase magically shrank in size, and it seems impossible to bring everything back with us. Be proactive by leaving additional room where you can.
Need a packing list? I’ve got you covered.
Now that you have the tools for success, let’s get it done.
3. Plan and Roll

Plan, plan, plan your outfits. Instead of packing a bunch of random articles and hoping they go together, spend some extra time planning out what you’ll wear. While you don’t have to know which day you’ll wear the outfits, it’s nice to have a gallery of looks to select from and it’ll cut down on the number of items you’ll bring. Say goodbye to the random five tee shirts you throw in “just-in-case,” knowing you’ll never actually need it. I plan my looks, try them on, and snap a photo so I can just search my gallery for what I want to wear for the day. Plus, you’re guaranteed to be on point because you’ve already put your outfits together! Next, we make sure to roll our clothing and place it vertically in the suitcase. Folding clothes takes up an extremely significant amount of space as compared to rolling. Don’t believe it? Try it yourself! It makes a world of difference. This is key. If you have bulkier items such as coats and sweaters, hold onto those and set them aside for a moment – more about that later.

4. Pouch Everything. Everything!
Makeup pouch. Toiletry pouch. Jewelry pouch. Feminine product pouch. A pouch for your pouch. Make like a kangaroo and pouch everything. No, I’m not sorry for my awful sense of humor.
On a more serious note, it’s very useful to pouch your items in categories to keep them organized and ready-to-go. You can’t bring any liquids into the aircraft that are more than 3 oz as well, so you’ll need to have some mini bottles on hand to transfer your liquid essentials into (see below). It also keeps your things more accessible and in order. It’s a huge space saver when your items are more condensed. Recommendations? Yes, please. These would also make awesome gifts for your traveling friends, FYI.
Jewelry Pouch:
Underwear Pouch:
TSA Approved Bottles for Liquids:
5. Be Strategic

Do you remember the old arcade game, Tetris? Packing a carry-on suitcase is just like playing a real-life game of Tetris – except with your own personal items. You must be strategic about which items you place where. Here’s a breakdown of how I segment my luggage, and which items I place in which bags.
The right side of my suitcase has straps to secure clothing items, so naturally I fit all my rolled-up outfits into that side of the bag.
On the left, you’ll find the bulkier items – such as outerwear, beach towels, blankets, thick jeans or sweatpants.
Where there are built in pockets on the suitcase, I pack my socks and undergarments. Other items such as belts, fabric hats, scarves, or sunglasses may also be best for this area as well.
In the duffel bag, my shoes are stowed in plastic grocery bags. Some people also like to use shower caps, but re-using plastic is a better solution for me personally. Also in the duffel is my makeup bag, toiletries (since you have to remove them during security), laptop, chargers, and other miscellaneous items such as a steel water bottle.
In Short…
To sum it up, here are the key things you can do to join #TeamCarryOn – and save yourself some money!
- Get the right luggage: a hard-shell carry on suitcase, and a duffel or tote bag (personal item) for underneath the seat in front of you
- Use a packing list to bring the essential items, and leave out the excess
- Roll your clothing tightly and preplan outfits to cut back on extra items of clothes
- Use pouches to organize small items by category, and transfer your liquid toiletries to 3-ounce containers
- Be strategic about where everything will go, and make the best use of the space you have available
You’ll be saving money on your travel in no time! Ready for your next adventure?


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