In 1973, designer Marley Hodgson stumbled across the estate sale of a recently deceased member of the British aristocracy. In his youth, that man had been a Ghurka officer – an Englishman trained to command Nepalese soldiers during the first and second World War. It was at that sale that Hodgson, a student of European history, had the million-dollar idea to fashion a line of timeless, functional, bespoke gear guaranteed for a lifetime (or more) of hard use.

Flash forward two years: Hodgson, using the late officer's paraphernalia as his guide, releases his debut collection. Then, over the next few years, a funny thing happened: With the widespread adoption of 'The Official Preppy Handbook' as style bible, suddenly every classics major worth his duck boots was carrying a Ghurka weekender to mummy's house upstate (those regular adds in 'The New Yorker' didn't hurt either).

The Gentleman's Umbrella, our newest obsession (and the latest addition to the Ghurka arsenal), is absolutely gorgeous at first glance, sporting a hand-stitched, leather-wrapped handle and luxurious, chestnut-brown exterior. Inside, a solid wood core supports a three-foot, four-and-a-half-inch canvas that's large enough to keep your entire body dry without altering the course of passing pedestrians.

During two weeks of testing on the windy streets of midtown Manhattan and downtown Brooklyn, the Gentleman's Umbrella held its ground, despite facing brutal, cross-town winds. Once home, the waterproof nylon coating easily shed leftover beads of water. Beyond its expected everyday functionality, the rich, tanned-leather-brown exterior won us compliments from friends, coworkers, and even a visiting Red Sox fan during a late-season sojourn to Yankee Stadium (whoever said sportsmanship is dead?).

Spend enough time on Ghurka's website and you'll learn Hodgson assembled his first product, a leather knapsack, for his young son nearly 40 years ago. Today, it's still in use – by his granddaughter. Despite the story's cheesy sentimentality, it surfaces the best thing about the Gentleman's Umbrella. Sure, three Franklins is a lot to spend when a seventy-dollar-number can get the job done. But like your class ring or a fine bottle of port, it's something you'll pass down to junior someday. So take care of it, will you? [$295; ghurka.com]