For the Neat Freak
Keep shoes separate from clothes and dirty away from clean with the Samsonite EZ-Cart: A detachable shelf divides your roller bag into two stacked compartments. Attached bungee cords allow you to piggyback smaller bags on top, while the flexible four-wheel system makes pushing the bag in front of you as smooth as wheeling it behind. samsonite.com, $290.
For the Dapper Dan
With its safari-inspired aesthetic, the Travelpro National Geographic Kontiki 22" Rollaboard might look right at home alongside Katharine Hepburn's cargo on The African Queen. Just check out the antique map lining and brass hardware. Fortunately, it's updated in all the right ways, with padded laptop sleeves and a rugged, DuraGuard-coated nylon fabric instead of canvas. travelpro.com, $149.
For the Multitasker
The REI Stratocruiser pulls double duty as a carry-on and a backpack, thanks to stowable straps. It also features a clip-on daypack, so you can keep in-flight essentials close at hand while your bag's overhead. And unlike other packs, which often topple when upright, this one comes with a "kickstand." rei.com, $239.
For the Adventurer
Most bags can handle travel by air, rail, or road-but how about by sea? Not an issue for the fully submersible Hummingbird Carry-On Zip. With its durable vinyl exterior reinforced with scrim (a latticelike material used in sails), the bag is tough enough to keep valuables safe in a rain shower, in a rain forest, or on a reef. cascadedesigns.com, $150.
For the Fashion Plate
The Hideo Wakamatsu Jelly Bean carry-on comes in four colors as bright and cute as its namesake and includes stickers, ideal for customizing the dimpled exterior to avoid baggage claim mix-ups. But the bag's not just a looker. The outer shell—made of the same plastic used in motorcycle helmets—will have you wondering why it's not called the "Hard Candy" instead. hideowakamatsu.com, $169.
For the Jetsetter
At five pounds, nine ounces, the GoLite TraveLite Wheeled Carry-On might seem like, well, a lightweight. True, it weighs two pounds less than leading competitors, thanks to its sturdy recycled nylon. But just because it lacks heft doesn't mean it lacks structure: Two internal compartments and two deep external pockets provide plenty of well-organized packing space. golite.com, $99.