Good shoes are the bedrock of a man’s wardrobe – the foundation on which everything else lies. Do you remember what happened to the man who built his house on sand? Well, neither do we, but we’re pretty sure it had something to do with him torpedoing a job interview by marrying a pair of leaky plimsolls with an otherwise perfectly good suit.

Thank the heavens, then, that it’s so easy to get the foundations right (with a little know-how). Though we live in changing times (celebrity presidents, moustaches, the return of the bum bag), the heroes of the shoe rack remain reassuringly constant.

To help you put your best foot forward all year round, we present 10 of the most iconic, unique shoes and boots of all time.

Timberland Classic 6-Inch Boot

The Timberland boot never wanted to be an icon. A humble, deeply practical work shoe designed for the laborers of New England, the Original Yellow Boot was built to outlast all its competitors and, crucially, keep its owners’ feet warm and dry during the snow-addled East Coast winters.

It did that through a combination of thick-cut nubuck leather, 39 separate parts, a revolutionary welted sole and a lengthy 80-step construction process. But then the nineties came along, and a hip-hop movement obsessed with larger-than-life garments and high-cut statement shoes dragged the Timberland boot from the worksite to the streets. And then the word was out.

Still made from the sturdy, no-nonsense materials of its 1973 prototype, the prerequisite work boot is a design legend that today does its best laboring teamed with selvedge jeans and chunky knits.

Sperry Authentic Original Boat Shoe

While sailing one summer on the Long Island Sound estuary just off New York, shoemaker Paul A Sperry slipped on the deck of his topper and fell overboard.

After hauling himself back on deck, the inventor resolved to develop a sports shoe that held its grip even on the damp surface of a sailing boat. This he did with the Sperry Top-Sider: a rubber soled deck shoe engraved with a revolutionary herringbone texture that maximized traction without adding bulk.