Tool: Timberland Boots, $190

FEATURES:

• Available in nine colors
• Runs about a half size large
• Rappers like them

I bought my first pair of six-inch Timberlands a few years ago, at a mall somewhere outside Sacramento, California, where I was visiting my parents for the holidays. I left the store with a large tan box; like several of my favorite sweaters and at least one Hawaiian shirt, the boots were an impulse buy.

I wore them through the muck and graying slush of a New York winter, where they performed with distinction, shooting to the top of my personal “Best Boots” list. They’re tan—specifically, “the color of wheat,” the site says—and thickly insulated, with a heavy sole. Because it’s been a few years, the leather is smeared, a little grayer; the heels are worn down from the pressure of my gait and the miles I’ve walked.

Since then I’ve rocked my Timbs just about everywhere: from a beach in Antigua to Fashion Week in Paris to a hike in the Adirondacks in mid-fall. This is because they are, I believe, a Platonic ideal—Aristotelian telos, or what the Dragon Ball Z–heads would call the boot’s final form. The Timbs’ perfection in the fiercely utilitarian realm is a holy thing. (Their only real drawback is that they are kinda heavy.)

What’s more, I’m convinced that the story of Timbs is the story of America, at least as it’s currently written—that’s to say, it’s the story of an immigrant who made good. This has to do with Timberland’s history. The company’s founder, Nathan Swartz, immigrated to America just before World War I. After apprenticing as a stitcher, the Odessa-born cobbler worked his way up to buying the Abington Shoe Company and bringing his sons into the family business. The Swartzes’ breakthrough, however, wouldn’t happen until 1965, when they figured out how to use injection molding on leather, which meant shoes that were fully waterproof via a leather upper fused directly to the sole without stiching. The boot that Abington produced was named Timberland in 1973, and, because of its immediate popularity, the Abington Shoe Company renamed itself the Timberland Company within months.

Then came the ’90s. Hip-hop happened, and so did cold-weather fashion. The craze was mostly powered by Duck Down Records rappers and the Wu-Tang Clan in New York. The Timberland Company wasn’t really on board; despite record-breaking profits, the suits worried that people were buying the boots for “the wrong reason,” according to a 1993 New York Times article. At the same time, Vibe reported that “everyone from thugs to step teams were stalking, walking in their six-inch construction boot” because...