There are boots for the backcountry and boots for the boardroom, but what about boots for everything else? Enter the Red Wing Iron Rangers. Introduced sometime around Cleveland's second inaugural, they sport double layers of leather over the toes (for durability) and outside-seam heel pockets (for comfort). They're also stain resistant and waterproof, and will soften, darken, and mold to your feet over time. And speaking of those double-leather toecaps: They're included for your protection, so put these to serious work in your garden and on easier trails.
At the office, dress up your Rangers with fitted flannel or jeans and a blazer. Come the weekend, pair them with new-fashioned Carhartt, especially if the words "oil change" are on your to-do list. Just don't worry when they scuff up, which will happen fast: The 100 percent natural, Amber Harness leather is pretreated with a combination of oil and wax, which encourages scars and imperfections to show through, all but guaranteeing a rugged, "I work with my hands" look – even for the millions of us who don't. [$290; zappos.com]
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