The pioneers of America’s paved highways kept chained pocket wallets so they could travel freely, riding fast or picking up stranded trekkers and roadside pies, alike.

A moto driver told me his chained wallet is a matter of fashion, though it’s handy, but for 1950s truckers, chained wallets were essential. These highway travelers were generally called Knights of the Road, known for helping hitchhikers or drivers less adept at navigating the open pavement. Chained wallets meant no worries about losing some essential object during random acts of chivalry. They helped fuel the mystique and toughness that made truckers known as modern cowboys - men could be men, and still keep their cash together.

Whether you’re looking for a chain or not, a trucker wallet should be built for the everyday uninhibited journey. No fuss, just sturdy, reliable and ruggedly good-looking.

Billykirk’s classic No.263-163 trucker wallet is made from American-sourced harness-grade leather, featuring a chain of dull nickel (nothing shiny), and a smaller version of this snap wallet has the same look, but is built to a metro pass-friendly size that makes it functionally modern.

I admit to preferring the unchained options, including the limited edition No.263 leather wallet in Olive - made from Argentinean leather with brass hardware, and a version in Tan Pebbled Grain from Chicago’s Horween leather company. The pebbled variety is ready-made with marks. Both are available online only while supplies last.

Chained, unchained, pebbled or otherwise, they’re all designed for today’s urban frontier, whether you're traveling by truck, train, bike or foot.