Obviously inspired by Volkswagen slogans, the Patagonia Das Boot ($175) is built for anything, with a TecTuff leather upper, a full toe box, waterproof construction, PrimaLoft Eco insulation and PolarTec 200 lining, an EVA footbed that molds to your foot, a Vibram trail outsole with Icetrek rubber for unbeatable traction, and a Patagonia Air Cushion Plus insert for comfort. Oh, and about that slogan thing? Totally joking.
Mixing hard working utility with casual style, the Red Wing Work Oxford ($275) lets you transition from worksite to dinner date with minimal hassle. Features include an Abilene leather upper, a Goodyear welt, and a thick sole that will keep your heels happy all day long.
A trustworthy duffle bag should do way more than just carry your stuff. It should protect it. Which means it should be incredibly tough and reliable, like the Best Made Co. Roll Top Duffle Bag. It's made using 1000 Denier Cordura — fabric so tough it's been a staple for the military for decades. It's also lined in 100% cotton twill with straps that are densely woven and adjustable for durability and extra strength. The Cordura is naturally resistant to water, but the polyurethane coated lining offers another heavy-duty liquid barrier, while taped zippers provide a third water-tight seal. Available in black or olive, and in 50L or 100L sizes. The Roll Top Duffle is built to last — whether you need it for a weekend trip or have to live out of it for a month.
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Short of sawing through your shoes, it's hard to imagine what all the various components look like. These Feit Hiker X Ray Boots ($315) get around this by using a transparent sole that lets you see the bamboo shank, cork footbed, and thread weave from underneath, while offering plenty of more worthwhile features like Horween Chrome Excel leather uppers, hand made Goodyear welts for added durability and strength, and two tone hiking laces for an added bit of style.
As far as "upscale" Chuck Taylors go, we're big fans of John Varvatos' upgraded All Stars — but if the rock/punk/distressed style isn't your thing, check out these Converse Chuck Taylor Clean-Crafted Oxfords ($100). These strikingly plain Chucks are upgraded with fine leather and trimmed in suede to give the classic sneaker a decidedly more subdued look while still differentiating themselves from the ones you can buy at JCPenney.