The Timbuk2 Checkpoint

El Naturalista (El Naturalista)

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CRUMPLER
From their inventive product names to a wide swath of limited-edition camera and messenger bags to demonstrating a bag's volume by showing how many bottled beers fit inside, Aussie-based Crumpler may be the most playful bag manufacturer out there. But beneath the whimsy are some of the most inspired products on the market, as is evident with their first roller suitcases. Parsed into three sizes, the Period Charmer ($350), Cork and Fork ($495), and Freestanding Edwardian ($520), all boast smooth rolling, loads of storage space, and Crumpler's unabashed love of dynamic color palates. With ample padded storage, the Cork and Fork is suited to the budding photographer and his costly accessories, but most weekenders will migrate to the Period Charmer. The water-resistant poly outer shell and ripstop inner lining offer the durability travel demands, and add-ons like multiple storage compartments, an easy access side-loading laptop sleeve, a top travel pocket, side and top handles, and an integrated laundry bag keeps everything in place. It can also transport a case of bottled beer (though it might violate TSA liquid limits).

TIMBUK2
Long established as one of the pioneers of sling-style messenger bags, Timbuk2 has recently applied its tri-colored dedication to a new line geared toward the weekend warrior in us all. As expected, the bags boast the durability and colorful aesthetic for which the brand is known. But it's the 1,001 little touches that really set them apart from the standard overhead fare. Witness the Checkpoint ($250). The company's first wheeling bag boasts removable skateboard wheels, a collapsible handle, and external pockets and straps for your boarding pass and various in-transit items. Inside, it's an OCD delight: two see-through zippered compartments line the suitcase lid (one that's removable—viola, instant toiletries bag), another large zippered pocket to separate your shoes from your clean clothes, felt-lined security pockets, and a sizeable compression pad to keep things packed tightly. Just choose the medium size; the large won't meet most overhead bin size restrictions. Timbuk2 also recently unveiled some new travel-centric packs, from their take on the traditional carry-on suitcase to a variety of organizational pockets.

EL NATURALISTA
This Spanish shoe company believes in travel. Their designers are encouraged to seek inspiration from the world's landscape, so that each piece of footwear comes with a story that denotes its place of inspiration. And while El Naturalista's line of bags has only five designs, the worldly aesthetic is undeniable. The soft-to-the-touch leather, wide stitching, clean patterns, and uniquely crafted metal clasps echo a natural, almost arboreal influence, while an interior zip pocket and vibrantly colored fabric lining lend a touch of the contemporary to create a truly stand-out shoulder bag (starting at $150).