The Chelsea boot still works best in dark colors, as recommended by Tony Gaziano of British shoemaker Gaziano & Girling, who notes that “an elegant pair of boots are these days more important than shoes” and that “a simple black Chelsea is a perfect alternative [to shoes], as it sits neatly under a trouser or jean cuff.” With its more formal roots, we recommend going for black leather, but suede and chestnut brown are also great alternatives that won’t date.

As they’re traditionally a narrower boot with a slightly longer toe, Chelsea boots are ideal with slim-cut jeans in black, grey, or navy. They double as perfect office attire, working well with the elevated look of a jacket, shirt and tie while also going smart casual as a weekend city boot to lift more casual jeans. Work the leather regularly with polish or treat them with a suede protector spray before wearing and you’ll have these boots for a lifetime.

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Desert Boots

Another supremely cool and practical style that has remained unchanged since its inception is the desert boot. Steve McQueen riding one-handed on a Triumph motorcycle in some, with only a pair of raw denim jeans, white T-shirt and white socks is testament to just how good they can look.

Like all great designs, this boot was born out of functionality. During the Second World War, soldiers fighting in the western desert campaigns sought out an alternative to their heavier military-issue offerings, which were impractical on sandy terrains. Needless to say, they weren’t learning how to wear boots with jeans, but that doesn’t mean the time hasn’t come.

The desert boot was the answer. It was made from two pieces of light, supple suede and featured just two eyelets – much fewer than most other boots of the time – which when tightly laced were designed to keep the sand out. And of course, there were its flexible crepe soles, which gave better grip and movement on the go.