To paraphrase an old Eddie Murphy line (and invert it): Luggage is like herpes. It stays with you for life.

And so we must take great care when making luggage decisions. To this end, I tested and ranked several bags, all from what has become the most beloved luggage category: the upright, wheeled, carry-on suitcase.

This is the kind of bag you roll down the aisle and stow in the overhead. The kind it seems everybody owns these days. It's hard to believe that this luggage format was not invented until the late 1980s (by a Northwest Airlines pilot), as it's so quickly become the ubiquitous choice for the short business trip or weekend jaunt. (So popular are "roll-aboards," in fact, that a few posh travelers, seeking to stand apart from the masses, have declared wheels passé and regressed to a life of shoulder straps. To each his own, I suppose, but I find shoulder-mounted luggage gives me a pain in my back and causes unpleasant frottage where the bag hits my hip.)

I tried six different luggage brands, at prices ranging from $50 to $575. All six bags roughly conform to the United Airlines size limits for carry-ons. These specifications (typical to most airlines) are: 9 inches (depth) by 14 inches (width) by 22 inches (height).

In addition to examining each bag's ease of packing, durability, looks, and so on, I administered several self-devised tests, including:

▪ The walking-around test, in which I walked around, rolling the bags behind me through the streets of my neighborhood.

▪ The rainy-day test, in which I set the bags out in the rain, to see if water would seep through.

▪ The fake-airplane test, for which I created—using pieces of living room furniture—a careful facsimile of an airplane aisle, which I then rolled the bags through. (I actually made two aisles: a 23.5-inch-wide aisle to mimic the Boeing 757, and a 24-inch-wide aisle to recreate the larger Boeing 767.)

▪ The butter-knife test, in which I savagely stabbed at each bag with a butter knife (partly to see if they'd puncture, but also to burn off pent-up air rage).

Luggage Lessons Learned

After much time spent unzipping zippers, peering into pockets, extending telescopic handles, and marveling at the icy hauteur of well-wrought ballistic nylon, I've concluded that there are five key elements to a quality carry-on suitcase:

1) Layout. Big, plentiful, well-designed pockets mean painless packing and unpacking. A hard-to-access central compartment or uselessly placed pockets will lead to an angry jungle of socks and sleeves.

2) Balance and Ergonomics. A good bag rolls smoothly on a wide wheelbase, with a sturdy, comfortably situated handle to guide it. A bad bag rocks drunkenly on its wheels, with a hard-to-grip, poorly angled handle. It's always finding ways to bump into your legs.

3) Durability. With a careful eye, you can suss out which bags are well-crafted and which will soon be plagued with sticking zippers and mangled handles.

4) Weight. The lighter the better.

5) Aesthetics. Because the point of the journey is not the destination—it's watching other travelers covet your bag.

Rankings

Taking into account both quality and value, here are my rankings, from worst to first:

L.L. Bean Stowaway Rolling T-Handle, $89 at LLBean.com.

This bag isn't awful, but at this price, you can do better. The bag's one central compartment has an undersized opening (not wide like a regular suitcase), making it hard to get at clothes at the bottom when the bag is fully packed. The T-shaped, telescoping handle was always slipping out of my hand—I think a standard, square handle is generally preferable. The bag's aesthetics aren't so hot, either. It looks like a backpack that's forgotten its shoulder straps. In fact, had it actually been a backpack (with wheels and handle as a secondary mode) I might have liked it OK. As it is, it's wrong for any sort of travel: not practical and stylish enough for city trips, yet not rugged enough for the outdoors. (Or do you enjoy wheeling your luggage through mud?)

U.S. Luggage 20-Inch Rolling Carry-On, $29.99 at Ebags.com.

This is the only bag that failed the butter knife test. I'd nearly given up on stabbing luggage, as the bags had all rebuffed my knife with impenetrable ballistic exoskeletons. But then came the U.S. Luggage bag. First stab and the knife went clean through—with a little popping sound. Totally unacceptable. Also, the handle doesn't lock into place when it's extended, so if you lean down on it, it disappears. At $29.99, this is essentially disposable luggage, and as such will do the trick in a pinch—as long as you don't need to hold much (it's undersized) or look good (it's crazy ugly).

Hartmann Intensity Collection 22-Inch Expandable Mobile Traveler, $460 at Hartmann.com.

This bag is gorgeous. It somehow makes 1050 denier ballistic nylon appear to be an elegant suede. And as for its ease of packing/unpacking, no other bag compares. It offers plentiful and well-placed pockets inside and out; easy-to-grip zippers; and a host of accessories—e.g., laundry bags and tri-folding garment hangers—built to match and neatly fit inside. So what's not to like? Some surprisingly basic stuff. For one, the wheelbase is too narrow—a good 2 inches narrower than many of the other bags. So the slightest disturbance while rolling the Hartmann along (if you hit a curb edge, say, or a flight attendant's foot) will set the bag oscillating back and forth over its wheels, until it flips all the way over and you're dragging it on its side. Not good. Also, the handle felt surprisingly fragile compared to some other bags—a bit loose in its moorings. The bag itself is also heavier than I'd like. For $460, I demand more than a pretty face and a lot of accessories. I want superlative performance, and I didn't quite get it.

Victorinox Standard Traveler 22-Inch Overnighter, $295 at Ebags.com.

The killer app with the Victorinox is that it converts into a backpack. (The straps can also be tucked away to make it a classic wheeled suitcase.) The backpack straps are well designed and the bag is comfortable on your shoulders, but I question how useful this feature really is. I guess on a trip with both urban travel and some more rugged hiking it might come in handy, but most trips that varied are also long enough to require a bigger bag. The other thing is that, to make it more backpacklike, the Victorinox has all sorts of additional, superfluous buckles and fasteners, which mostly just get in the way. Finally, it was the only bag to fail the rainy day test. (OK, the cheapie U.S. Luggage bag also failed, but only because I'd stabbed a hole in it.) Its compartment began to fill with water and would have soaked any packed clothes clean through. Otherwise, this is a pretty solid, if pricey, piece of luggage. It's got a simple but appealing shape, a nice layout of pockets, and an included tri-fold suit hanger. It seems excellently constructed. You wouldn't go wrong with it. But for $155 less, you could get the …

Samsonite Ultra 3000 XLT Sideroller Carry-On Upright Suiter, $139.99 at Ebags.com.

Nothing flashy here. Completely generic, Samonsite-y looks. Yet it's a great value for its price. In terms of functionality, it's not appreciably different from the high-end bags. The Samsonite features oodles of useful pockets inside and out and is again well-appointed with accessory bags and a tri-fold hanger. The wheels are rollerblade style and feel strong. The main compartments are quite spacious. And here's the kicker: Separate, tiny wheels let you crabwalk the bag sideways, to create a narrower profile when you need to squeeze through a tight space. I tested this out in my simulated airplane aisles and was impressed. I could easily picture the Samsonite slipping untouched through a slalom of obese airline passengers, their fat haunches spilling under armrests and into the aisle. The little sideways wheels aren't all that strong and don't roll as smoothly, but they'll do the trick for that mad jaunt from the jetway to your seat. Granted, if the Victorinox and the Samsonite were the same price, you'd want the Victorinox, but the cost difference is way too much to be overcome. Unless you're talking about a bag like …

Tumi Vestry 22-inch Wheeled Packing Case, $295 at Tumi.com.

In the luggage brand senior yearbook, Tumi was voted "Most likely to be stowed in a Phnom Phen airport locker, bulging with stacks of non-sequential U.S. currency." Tumi designs are always sleek, modern, and just a little bit dangerous. The Vestry model is no exception, with its bold, black, streamlined look. It also excelled at each challenge I set for it. It rolled more smoothly than other bags in the walking-around test; did not leak when subjected to the rainy-day test; fit comfortably into my simulated aisles in the fake-airplane test; and seemed to almost chuckle dryly as, during the butter-knife test, I feebly attempted to injure its thick and muscular hide. You can feel the solidity of the construction—the unbreakable zippers and unbendable handle. With its excellent layout of compartments and pockets—including dedicated shoe slots—the Tumi is delightfully packable. It's lightweight, too.

And so we have a winner. One look at this bag and you'll long to strut confidently through foreign airport terminals, Tumi rolling alongside. A tad expensive? Yes. But remember Eddie Murphy's farsighted wisdom. A bag like this will stay with you for life—and that's exactly what you'll want.