On a recent flight from Dublin to Edinburgh, the gate agent delivered news that made my heart sink: “Ma’am, you’ll need to check that roller bag. The plane is small, and that won’t fit in the overhead bins.”

Look, I’m usually a carry-on-only warrior—the thought of checking bags makes me break out in hives. But this was a non-stop flight, so I convinced myself my beloved Away roller would actually make it to my destination instead of taking an unplanned vacation in Uzbekistan.. Little did I know that my spine was about to pay the price for this moment of trust in an airline.

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Without my roller bag for it to rest it on, I found myself trudging through both Dublin and Edinburgh airports with my personal bag slung over one shoulder. Usually, it sits perfectly balanced on top of my wheelie as I glide through concourses. Instead, I was hunched over like Quasimodo, and by the time I reached Scotland, my back was screaming in protest.

When I returned to the States and limped into my physical therapist’s office, she listened to my tale of woe and delivered her prescription with the matter-of-fact tone that only medical professionals can master: “Use a backpack instead.”

What I Need in a Personal Bag

I love my personal bag—even though it’s looking more tattered than a pirate flag these days. It’s been my faithful travel companion for years, fitting perfectly under airplane seats and swallowing up all my necessities. It was like Mary Poppins’ carpetbag, but less magical and more practical.

I have five requirements for my personal bag.

But I’m also very interested in not experiencing back pain that makes me walk like I’m auditioning for a zombie movie.

So began my quest to find the perfect personal-bag-sized backpack. I had specific requirements that any contender would need to meet. It must:

• fit airline personal bag dimensions (basically 14 x 18 x 8 inches)
• accommodate my laptop
• include a sleeve for sliding over my roller bag handle
• feature logical design for in-flight accessibility
• most importantly, hold everything my current bag has been carrying for years

That “everything” includes a surprising amount of stuff: electronics and adapters, my computer, a purse I would use once reaching my destination, a first aid kit for my Next Tribe travelers, makeup bag, Bluetooth noise-canceling headphones, toiletries, medication, velcro rollers (don’t judge me), a bulky but useful hair appliance, glasses case, various chargers, and my TSA-approved liquids bag.

Here’s what I discovered.

Solo New York Laptop Backpack

My first candidate was the Solo New York Laptop Backpack, a lightweight polyester option designed for business travel. At 18 x 13 x 7 inches, it promised to be carry-on friendly with a fully padded laptop compartment and lockable zippers. The backpack also featured an external USB port and RFID data protection pocket. And the price is right–$35.99.

The zipper strained like it was holding back a dam.

The laptop compartment worked well enough, and I managed to squeeze in my chargers and headphones. There was even space for my electric hairbrush and makeup bag. But here’s where things got dicey: the bag was stuffed tighter than a Thanksgiving turkey. I could barely close it—actually, I couldn’t really close it at all. The zipper strained like it was holding back a dam.

When a bag can’t accommodate everything I need, it fails the most basic test. Sorry, Solo, but you’re sitting this dance out. Yes, it’s cheap but a pain-free back is priceless.

Read More: The Best Carry-On Bag? Our Founder’s Surprising Pick

Cotopaxi Allpa 28L Travel Pack

The Cotopaxi Allpa 28L came with impressive credentials: made from 100 percent recycled fabrics (27 recycled plastic bottles, to be exact), suitcase-style organization, and multiple zippered mesh pockets. At 19 x 12 x 9 inches, it was slightly larger than ideal but still within personal bag range.

Cotopaxi knows how to make gear that doesn’t look like it was hatched by someone with the design skills of a CPA..

I loved the vibrant colors—Cotopaxi knows how to make gear that doesn’t look like it was hatched by someone with the design skills of a CPA. (No offense tao the artistic CPA’s out there!) The brand has a solid reputation, partly due to its commitment to sustainability and fair trade, all that jazz. And the construction felt sturdy. Everything from my old bag fit, though just barely, and the luggage pass-through strap looked robust enough to handle airport chaos.

But here’s what killed it for me: accessing anything required archaeological excavation. Items settled to the bottom like sediment, meaning I’d have to unpack half the bag to reach my phone charger. When you’re dealing with the stress of air travel, the last thing you need is a bag that makes you play Jenga every time you want to grab something. Love you anyway, Cotopaxi, but accessibility matters.

Samsonite Xenon 3.0 Slim Laptop Backpack

Next up was the Samsonite Xenon 3.0–the medium size measuring 6 x 12 x 16.5 inches with a low-profile design. It featured a padded laptop compartment, tablet pocket, and what Samsonite called “well considered business organization” in the main compartment. The laptop went in fine, and there was room for some chargers and adapters, but when I tried to add my hair appliance and makeup bag—the two items I call “the biggies”—the bag didn’t work for me.

When I tried to add my two biggest items, the bag threw in the towel.

Even worse, the luggage pass-through strap looked like it was designed by someone who had never actually seen a roller bag. It was a thin, wimpy little thing that inspired zero confidence. If I’m going to trust a strap to keep my bag secure while racing through airports, I need it to look like it could tow a small car, not snap if I look at it wrong.

This one got the boot faster than you can say “insufficient storage capacity.”

SwissGear 1900 Scansmart TSA 17 Laptop Backpack

The SwissGear 1900 Scansmart promised to speed me through airport security with laptop-in-case scanning capability. It boasted an enhanced laptop compartment for 17-inch laptops, a padded tablet pocket, and multiple organizational compartments including an RFID-protected section and accordion file holders.

It was like a Swiss Army knife had mated with a filing cabinet.

Here’s the thing about the SwissGear: it’s a victim of more-is-better reasoning. There were zippers everywhere—front pockets, side pockets, internal pockets, secret pockets, pockets within pockets. It was like a Swiss Army knife had mated with a filing cabinet and produced this organizational monster.

I spent ten minutes just figuring out what was supposed to go where. The laptop fit fine, and there was plenty of space, but the bag suffered from too many bells and whistles. Plus, the luggage strap was another one of those flimsy afterthoughts that looked like it would surrender at the first sign of turbulence. Hey, SwissGear: Sometimes simple is better.

CalPak Terra 26L Laptop Duffel Backpack

The Calpak Terra 26L caught my eye on Instagram (yes, those targeted ads work on me too). Made from 27 recycled plastic bottles and weighing just 2.7 pounds, it featured a clamshell opening, padded 17-inch laptop compartment, and that all-important luggage trolley sleeve. The bag promised to fit as a personal item on most airlines while offering “surprising spaciousness.”

The glossy finish looked sleek, and I appreciated that it didn’t have the tactical/camping vibe of some other options. My laptop slid into its padded compartment easily, and there was decent space for everything else. The bag also had a front pocket for items I’d need quick access to during flights.

Then I discovered what I can only describe as “pocket paralysis.”

But then I discovered what I can only describe as “pocket paralysis,” which felt even more overwhelming than the Swiss Gear offering. There were straps and zippers everywhere—some leading to actual pockets, others seemingly opening into the Bermuda Triangle. When you have seventeen different compartments, you spend more time remembering where you put things than actually using them.

The Terra looked good on my roller bag, but I could already imagine myself frantically searching its deep recesses for my phone charger while passengers behind me sighed audibly. Hard pass.

Osprey Daylite Expandable Travel Pack

Osprey has always been a brand I trust—I’ve used their hiking backpacks for years. The Daylite Expandable comes in at 26L with internationally accepted personal item dimensions (accepted by 85 percent of major airlines, according to their marketing). The bag featured an expandable main compartment that could add six liters when needed, transforming it from personal item to standard carry-on size.

What immediately appealed to me was the clamshell design with a full-zip opening. Everything went in easily: laptop in its dedicated sleeve, electronics, the cumbersome curling brush, makeup bag, and all my other essentials. The bag felt substantial but not heavy, and the bright color options meant it would look great with my orange Away roller.

A bag that understands that travelers want simplicity, not a treasure hunt.

The real test came when I slid it onto my roller bag. The luggage pass-through was well-designed and secure—no flimsy straps here. The bag sat properly and wouldn’t look suspiciously overstuffed to gate agents. Plus, that expandability feature was brilliant. If I encountered a friendly flight attendant, I could expand it for extra space. If I got someone having a bad day, I could keep it compressed and avoid any sizing disputes.

The organization was logical without being overpowering. A few well-placed pockets, easy access to the main compartment, and no confusing maze of zippers. Finally, a bag that understood that travelers want simplicity, not a treasure hunt.

Portland Gear Cascade Backpack

My final contender was the Portland Gear Cascade, another Instagram discovery that caught my attention with its unique top-opening design. The bag featured weather-proof construction, a wireframe top for easy access, hidden security pocket, and what they called “Easy-See” grey lining for improved interior visibility. It also promised to stay upright when set down and fit under all standard airline seats.

The top-opening concept intrigued me—no wrestling with skinny slits to find my things.

The top-opening concept intrigued me—no wrestling with skinny slits to find my things. Everything fit nicely, and I loved that it had dedicated water bottle sleeves. The bag went onto my roller effortlessly and looked proportional, not like I was carrying a hiking expedition on my back.

But despite these positives, something felt off. The bag seemed to be straining at maximum capacity, like it was holding its breath. While the top access was convenient, I worried about items shifting around during travel or things falling out when I opened it mid-flight.

And the Winner Is…

After testing all the contenders, I eliminated everything except the Osprey Daylite and the Portland Gear Cascade. Both fit my requirements and felt well-made, but they represented different approaches to the same problem.

After living with both bags for a few days and really considering how I travel, I chose the Osprey Daylite Expandable Travel Pack.

The deciding factors came down to versatility and trust. That expandability feature is genius—it’s like having two bags in one. When I’m being conservative about sizing, I keep it compressed. When I have extra souvenirs or encounter a relaxed gate agent, I can expand it for more space. The clamshell opening, while initially seeming more complicated than the Portland Gear’s top access, actually provides better organization and security. Everything has its place, and nothing falls out when I open it.

The deciding factors came down to versatility and trust.

The laptop compartment is perfectly padded and positioned, the outside pockets are strategically placed for in-flight essentials, and the overall construction screams quality. Most importantly, it slides onto my roller bag handle like it was meant to be there, creating a stable, secure combination that won’t tip over or slide around.

The Osprey also doesn’t suffer from pocket paralysis—it has just enough organization without making me feel like I need a PhD in bag navigation. And those bright color options mean I’ll never mistake someone else’s boring black bag for mine.

My back already feels better knowing that my shoulder-bag days are numbered. The Osprey Daylite isn’t just a replacement for my old bag—it’s an upgrade to my entire travel experience.

This my honest review and nobody’s paying me to write this!