The Grenson brand goes back to 1866, when William Green, who had been making boots in his childhood cottage in Northamptonshire, England, set up a more formal production system. Greens Yard, launched in 1874, became the first factory in the world to use Goodyear welt construction, a game-changing method of attaching the boot upper and insole to the bottom sole by means of a "welt" strip. You don't have to know the ins and outs of cobbling to appreciate the chief advantage of Goodyear welting: This time-consuming manufacturing process means that shoes can be resoled repeatedly, over decades and sometimes indefinitely. Grenson shoes have a hell of a half-life.

The heritage English shoes are an investment few men make lightly, but the arithmetic works out. They say you haven't even broken these expensive shoes in until you've had them resoled multiple times. And, despite its Victorian roots, the company is less stodgy than one might suspect. Grenson wares are smartly offered in three classes: G:Zero, G:One, and G:Two, plus the limited-edition G:Lab series, which includes experimental options in mixed materials, including a suede-and-camo canvas, crepe-sole derby. The more accessibly priced G:Twos are the entry-level option.

Our pick of the collection is the G:Two Jacob boot, a city-ready merger of two iconic British styles, the punched wing-tip brogue and the Chelsea boot (the short jodhpur boot worn by a varied cast over the years, including Beatles, Stones, and Stormtroopers). The elastic siding and back pull tab make these a breeze to get on and off. We're also fans of the natural-colored double leather sole, which provides a little gentle visual texture against the all-black body. Classic, hard-wearing, and undeniably cool, this is one pair you’ll keep around for the long haul. Good news: Grenson itself does some top-notch resoling work[Jacob boot, $435;]