How to choose a Carry-On bag for your next Adventure?
With carryon bags there are so many choices to choose from, wheels wheels, duffel bag to suitcase style, hard sided and soft sided, lots of pockets, four wheels or two, zipper or latches, cheap or expensive, and so many others to choose from. As we travel for both pleasure and work we have been through multiple different bags and even have different ones in the house that get broken out for different occasions. My wife and I both also have different needs and techniques for packing so those reasons drive our differences in packing and how we organize ourselves.
Duffle Bags
The cheapest and easiest of all carryon bags would be the duffle bags. We have found some advantages as well as disadvantages to these. We also have a few different ones that we recommend for different uses and price points. So let’s start from the most basic and move up from there. Coming in under $20 is this prefect collapsable duffle. If you just need something that will hold clothes and be able to carry on for that quick trip this is perfect. Our reason for getting this is to use as a bag on vacation as well as getting things home. It is so great to have an extra bag so when you purchase something and want to get it home you have space. We generally will pack this collapsed into our other bags and then on vacation if we are moving a lot we dont need to pack as condensed as we did to get there as well as if we make a purchase we have space to bring it back.
The next on the list would be a traditional duffle. For these bags we really like just a normal 
gym duffle similar to the one in the link. Yes it does mean you have to carry it but having a gym bag will get you a shoulder strap, a larger opening in the top, and multiple compartments. The shoulder strap is huge when you overload the bag with clothes and then having to carry it across that long layover in the airport. The large top opening is crucial for the way we pack with packing cubes. It will allow for them to be pulled out and put in easily without having to unpack the entire bag. Finally the gym bag will have a shoe pocket that is great for the extra pair of shoes as well as dirty clothes or anything that you dont want to be touching or near your main pocket stuff.
After the gym bag we have probably the best kept secret to travel duffle bags, the water resistant duffle. There are many different ones both of our kids use the one from Eagle Creek on every trip. I use this one, it is a bit larger and harder to carry as it can hold a serious amount. In we love these bags as they are great moving between rental houses, going out on boats, and taking any transportation in any weather. As said before they are mostly one chamber, heavy duty zipper and waterproof material. We can drop them on the sidewalk, take a splash in a water taxi, and be out in the elements and I dont worry one bit about the things inside the bag. One plus to both of these bags is the handles are designed in a way that you can use them as a backpack so it makes carrying them a breeze.
The final bag would be the Convertible Garment Bag for him and for her. 
These bags are not something that we use, we just dont wear much dress clothes for either of our travel professions. We do recognize the positives about these bags though as a smaller alternative to a garment suitcase as well as more protection than just a suit or garment carrier. They also bring a bit more style and space to your carryon. There is plenty of space to pack for multiple days and multiple occasions. So if you are looking for a great bag to go to the weekend wedding, stay business formal or any trip that requires hanging clothes this is a great choice for you.
As with all bags they have some drawbacks. 
No wheels means that you have to be ready to carry what ever you put in there, this can be tricky if your trip requires a lot of walking. A second downside is the way they pack. For the most part they are smaller and harder to incorporate the packing cube method that we have talked about in previous posts, with that the MIER bag does hold 4 medium cubes very well. Finally is the protection, because they are all soft sided if you are carrying fragile things it does put them in some harms way when cramming them into an overhead bin or if it needs to be gate checked. Overall these bags are great for what they are designed, they can take a lot of stuff from one place to another and keep the elements off of them.
Roll Aboard
With Roll Aboard there are so many options ranging from cheap $50 bags all the way up to some of the most expensive with Tumi and Ramowa. We have a few that we swear by. My wife and I both have a different view on preference but any of these that we recommend have been well traveled and trusted bags.
The first one is the OGIO Layover bag. I purchased this as my first carry on bag when I began traveling for work full time. There were so many features I loved. The interior straps kept everything in place and it never looked like I was opening a can of worms in security if they needed to open it. The two pockets on the front were great for toiletries, wallet and any other small thing that I needed to shove into a pocket while traveling. I never had a single problem with the wheels or the handle, it still handles and rolls like it did when I got it. The nice added perk was the expansion zipper, once it is expanded then it goes past the carryon size but usually I was able to get to the flight no problem. And with the way united has you put your bag in the overhead bins it does fit. My only downside with this bag was that over time it started to show its age with some of the fabric fraying. Otherwise it is still sitting and ready for a trip if I need it.
The next bag is the Travel Pro Crew. This is my wife’s bag of choice. 
With the addition of the J Hook, it allows her to drag her backpack around on the bag just like any Pilot you see rolling around the airport. So this bag has the ability to hold ALOT which great, she usually packs in 2 medium and 2 small packing cubes, toiletries bag, makeup bag, shoes and a few other things. This is all able to fit without even getting into the expansion. The added pockets in the front and back also make for some great spots to hide work paperwork, or more things you need for your vacation. It’s surprising but she has even lost clothes in the pockets of this bag because she didn’t realize it had that much space. Our only complaint is the handle has a bend to it to make it more ergonomical. And for us coming from straight handled bags it is just awkward.
When it comes to carrying very fragile things you can never discount a Pelican. The Pelican Air 1510 is by far the best choice for this. We use it anytime we are carrying camera equipment, computers or just electronics in general. If I am able to fit my clothes in my backpack this guy will take everything else and I dont ever worry about the things inside it. You will need to add an insert to it in order to protect your stuff, those can get very personal to what you want to put in there. My other suggestion is that if you are going places that you have to leave it in the open often unsupervised they do attract attention. Pelican is known to protect your valuables so people see them no matter what as to be something carrying something expensive.
The final carryon that we use is an AWAY Carry On. 
This bag does live up to all the hype. Before a month long trip to Australia I decided to just give it a shot and I have never looked back. I seemingly can fit anything into this bag it has yet to say no that’s too much. Including mask, snorkel and diving fins. The Internal organization is great. I use one medium and one small cube on the open side along with a shoe bag for a second pair of shoes. The other side can hold endless pants, sweaters, and nicer clothes. The zipper is a BEAST, I have stood on top to zip it closed and once it is zipped it has yet to pull apart. Having the charging block in it is nice but after every gate agent asks me to take it out I now just leave it in my backpack. Otherwise it looks good as new and has more miles on the wheels than some cars. When I say it has been everywhere it has and I have never treated it nicely. For me this is a tool and when it stops working it will get replaced. I hope that it never stops.