Organizing items in your suitcase or backpack should be a one-time thing, but that’s rarely true. Even if you save space by rolling your clothes and arrange your gear in a Tetris-like formation, things seem to explode the second you land at your destination and unzip your bag. Even worse, dirty laundry and souvenirs make you rethink your whole packing strategy, and staying at multiple properties means that you’ll have to do it over and over again. Thankfully, the FlipSide luggage suite tackles this issue—but did it really make packing easier for me?
I’ve spent much of 2026 testing three of the brand’s bags, including the 22-inch Ryan Carry-On, 26-inch Ryan Checked Bag, and the FlipSide Backpack. And I’m delighted to share that in a world of premium bags to choose from, these actually made a difference. This is largely due to one design element that both improved and simplified my packing experience — a zippered divider that let me split each bag into two distinct packing areas.
I cut back on packing cubes and organizers and embraced a simple plan. One side could serve as my clean clothing compartment, while the other could hold dirty clothes. Or I could enlist one side for my wearables while using the other for electronics. With the larger suitcase in hand, I could arrive at my destination with a half-packed bag, filling the empty compartment with take-home gifts without my pack bursting at the seams.
And with three different bags to mix and match depending on the trip, I never needed to compromise space, making sure I could bring (and take home) exactly what I wanted. Whether you need one solid suitcase for streamlined organization or want to invest in a complete set for various occasions, here’s a breakdown of the three FlipSide bags I’ve experienced, so you can decide if they’re right for you.
FlipSide Backpack: The overnight and weekend getaway solution
The FlipSide backpack offers the best of both worlds—the convenience of a personal item paired with the accessibility of traditional luggage. As with all FlipSide bags, there are two adjustable packing areas in the main section, separated by a sturdy yet flexible cloth divider. This means that you can put your electronics and toiletries on one side while packing your clothes into the other.
You can use it like a normal backpack and remove items from the top, or fully unzip and access both of the packing compartments similar to a traditional piece of luggage. There’s also a padded laptop sleeve that can fit devices up to 15 inches and two zippered pockets in the front, where I stash my passport, wallet, phone, and other essentials as I breeze through airport security.
You’ll also find two side pockets on the bag’s exterior, perfect for stowing a water bottle or umbrella. Ample pockets help organize odds and ends while reducing the need for separate pouches. There are 6 interior pockets, mostly made of mesh for visibility, keeping items secure no matter how bumpy your journey gets. There’s also a key loop so those don’t get lost in the bottom.
I was surprised by how sturdy yet comfortable the backpack was in real-life scenarios. The bag is well constructed, made from heavy-duty 1680D nylon. Padded shoulder straps help reduce fatigue when commuting for long stretches of time, and a chest strap helps distribute the weight more evenly.
There’s also a trolley strap that lets you secure your backpack to a rolling suitcase if you’re using the backpack as a personal item, and a padded handle on top. These clever features make it easy to carry the bag without needing to slip your arms through any straps.
FlipSide 22-Inch Ryan Carry-On: Versatile travel without checked bags
The FlipSide 22-Inch Ryan Carry-On is my favorite of the bunch, as I think it’s suitable for 80% of travel. I’ve used the roller bag on both overnight and two-week-long trips and found it was the perfect size for both occasions. The 22-inch size comfortably fits in an average plane’s overhead bin, so I never had to check a bag while having everything I needed at my disposal.
And in a pinch, it’s easy to check, which I found extremely helpful once I realized I wanted to bring full liquor bottles back with me on a recent trip exploring Peru’s most iconic stops. The Ryan boasts a solid exterior that feels soft but holds up to the elements and maintains rigidity. The handy tracker pouch and built-in ID tag help quell my worries when it needs to go into the cargo hold section of a plane.
The two adjustable compartments in the bag’s main section can hold about seven of my outfits, give or take a few depending on how many bulky items are inside. There’s a large mesh interior pocket that I use for toiletries and a narrower mesh pocket that fits a pair of shoes, as well as two exterior compartments where I slip my tablet and travel documents for quick retrieval. The construction is solid, with a comfortable extending handle and durable zippers that stay closed.
For longer trips, I pair the Ryan with Flipside’s personal bag, which I use for protecting work gear and delicate electronics. Then I utilize one side of the carry-on for clean clothes, moving them over to the other side when they’re dirty. This has reduced most of my rummaging, and I can expand the dirty section after the halfway point of my trip, so there’s a good ratio of space for all of my belongings.
My other use case, on shorter trips, is to only travel with the carry-on. In this scenario, I’m placing all my clothes on one side, and my non-wearables on the other. I then bring a single packing cube for dirty laundry, and everything has a predictable, easy-to-access home.
FlipSide 26-Inch Ryan Checked Bag: The organization solution for extended travel
FlipSide’s 26-inch Ryan Checked Bag has convinced me that carry-on isn’t the only way, and it’s designed to reduce overwhelm on longer trips. I mean week- or year-long trips, with all the space you need without turning into a bottomless pit of “Where did I put that?”
The layout is nearly identical to its smaller carry-on counterpart, with two adjustable panels that separate your items, two larger mesh pockets, and two exterior pockets. The main difference is size: the checked bag offers almost double the interior space of the carry-on. Its empty weight is 12 pounds, making it a lighter option than a hard case, which is important for those who stuff their checked bags to the gills.
Even with its impressive capacity, the Ryan Checked Bag is easy to maneuver, with precision-glide 360-degree wheels, large metal heavy-duty zippers, and an ergonomic retractable pull handle. I could whisk the bag through an airport or down the street while using my other hand to look at my phone or carrying another item. No matter how frenzied I was, the bag dutifully trailed and pivoted behind me.
If you prefer more space, FlipSide luggage also sells a 29-inch variant, with an estimated 28% of additional interior space than my 26-inch roller bag given its measurements. It’s just one inch below the usual checked-bag limit, letting you squeeze by airport staff with as much packing space as possible.
Putting it all together: How the FlipSide luggage suite can fit everything you need
I’ve only used the FlipSide luggage separately, but I see how the three items would harmonize together on a longer, more ambitious trip. Let’s say I plan to return to Mexico’s cultural gem, Meridafor a month-long journey that mingles pleasure, adventure, and a bit of obligatory work together.
Here’s how I’d use my three FlipSide accessories together to cover all of my bases:
- FlipSide Backpack: My backpack serves as my workstation. I’d stow my laptop in the padded section, cameras and media tools in one main compartment, and my charging accessories in the other.
- FlipSide 22-Inch Ryan Carry-On: This bag is designated for clothing. I’d bring seven outfits and cycle them between the clean and dirty interior compartments, resetting the bag each week while washing my clothes at a local laundromat or enlisting hotel services.
- FlipSide 26-Inch Ryan Checked Bag: The checked bag is for everything else, items that I’ll only use at the destination and won’t have use for during actual travel. On one side, I’d put adventure and outdoor gear. In this case, that’s snorkels, hiking boots, binoculars, and extra clothing layers. I’d leave the other side of the bag empty, planning to fill it with souvenirs and personal gifts to bring back home.
And with just three bags, I’ve satisfied every use case I may have while traveling abroad. I’d also use these bags in two-player mode. When traveling with a companion, I could use each compartment to divide my stuff with a friend. Three bags between two people is much more manageable than six separate ones, as long as you trust your companion to leave your sections alone.
In all honesty, I’ve never traveled with all three Flipside bags at once. They’re so space efficient and well organized, the truth is I don’t really have to. But that’s precisely what makes this set stand out. It doesn’t take much thought to streamline your packing into one, but you can dream big and use all three when you want to bring everything and the kitchen sink. It’s a set meant for range and flexibility, without a lot of forethought, firmly earning it the top position as my favorite travel set.
Source: www.themanual.com
