Timbuk2 Never Check 4 Wheel Spinner ($289)
There’s no boarding blunder quite so demoralizing as trying to jam a too-big carry-on into the luggage sizer while irate fellow passengers scowl at you—except maybe being forced to gate-check it. But as the name suggests, there’s no danger of that with Timbuk2’s new fun-size roller. At 20 by 13 by 9 inches, it’s guaranteed to be small enough for cabin duty, yet its 33 liters are surprisingly roomy, with space enough for a long weekend’s worth of clothes and accessories. That’s thanks to two mesh organizer pockets for smaller items, a larger pocket for shoes, and compression straps in the main compartment to cinch down duds and maximize space. On the outside, front and back stash pockets are perfect for electronics or travel documents, and padded side handles make slinging the Never Check into the overhead bin easy. (That the bag weighs just 6.8 pounds doesn’t hurt.) It’s all topped off with heavy-duty seams, a durable telescoping handle, and a lifetime warranty. The minimalist design is stylish enough for business trips, while the weather-resistant, wipe-clean Cordura fabric and burly wheels won’t be outgunned on an adventure-filled weekend with friends.
Burton Wheelie Sub ($400)
Best Checked
If you’re on a monthlong expedition or just want to haul a lot of gear, this double-decker, 116-liter roller bag is a delight. It has separate compartments to keep your clothes organized, plus stretchy material around the zippers for some extra give in case you need to cram in a ton. To make managing all that stuff even more effortless, the bag splits in half down the middle, so you can avoid single-bag overweight fees. (Don’t worry, the zippered flaps you expose when doing this can take a beating.) Smooth-rolling wheels, lightweight construction, cushy grips, and a low-profile, telescoping handle make lugging the whole thing comfortable.
Peak Design 45L ($300)
Best Carried On
Quite simply, this is the perfect travel pack. Not only does it have a main compartment that zips all the way open like a carry-on roller bag, but it also has side zips for quick access. There are pockets for just about everything, including a hidden one for passports, a soft-lined one for sunglasses, and a padded one for a laptop. A streamlined silhouette incorporates extra-cushy shoulder and waist straps that stow beneath a magnetically sealed back pad, and an innovative snap system shrinks the bag to a 35-liter daypack. The outer material—100 percent recycled, weatherproof, 400-denier nylon canvas—is as functional as it is sustainable.
Granite Gear Cross-Trek 2 Carry-On Wheeled Duffel with Removable Backpack ($210)
Most Versatile
This ingenious roller bag comes with a pack that hitches to the front with a sturdy 360-degree zipper. Use each piece separately, leave the pack attached for easy rolling through airports (then detach and stash under the seat while you throw the duffel in the overhead), or check the whole thing. Both components feature strong water-repellent zippers, burly nylon, and durable wheels. The pack has foam-padded shoulder and sternum straps that tuck away, handles for easy loading, and compartments for accessories.