The perfect combination of fashion and shoes

Casual trousers are trickier. If you’re going to wear black shoes with chinos in the brown spectrum, then stick to less formal styles. “A derby looks better than an Oxford as it’s a bit chunkier and more relaxed,” says McDonald. The same goes with jeans. “Oxfords would only ever work with very slim black jeans, and even then you’re going to look like a forgotten member of the Libertines.” If you insist on black shoes with your dark denim, then it’s best to go for something like Chelsea bootsor Dr. Martens.

If you’re the kind of guy who likes his chinos colourful, then the sudden shift to black shoes can feel a bit severe. You can lessen the impact by cuffing the hems and even losing the socks, and making your shoe style as dressed-down as possible loafers are preferable to anything with laces.

Finally, you should probably avoid shorts and black shoes once you’re out of school uniform.

BROWN SHOES

Brown is the most forgiving shade of smart shoes. The breadth of browns available means that there’s a tone for almost any situation, bar the very smartest offices; even a pair of bespoke chocolate John Lobbs will have you blackballed in some investment banks. But with anything other than a black suit or tuxedo, brown shoes add personality and feel a touch less stuffy.

“The lighter the shade, the more relaxed the look,” says McDonald, “particularly if you add detail, too.” A pair of brown brogues are less formal than the same shade Oxfords, for example.

Away from tailoring, brown should be your go-to for chinos of any colour, although be careful not to match too closely; like with double denim, you want at least two shades of difference between your trousers and your shoes, lest you look like you’re wearing the bottom half of a onesie.

Darker browns look great with indigo denim but can work just as well with more washed out shades. Just make sure that you step down into a less formal style — suede Chelsea boots are perfect, as are chunky brown worker boots.

Black jeans and brown shoes is a minefield of differing opinion and one not worth marching into if you’ve any personal doubts. But if you’re confident, then it’s a look that can work, so long as you stick to shoes in a shade that’s nearer black than tan. Although again, boots are easier to pull off, here, particularly Chelseas, which give you the air of someone who’s just left One Direction to find a direction of their own.

OXBLOOD SHOES

Though technically a colour, oxblood can act almost as a neutral. They tend to work in almost exactly the same way as brown, although because they’re a touch bolder. They tend to lend whatever you’re wearing an ounce or two more of personality. “Making a statement with smart shoes shouldn’t mean going too far out of your comfort zone,” says Vieira. “Instead of opting for an extravagant style, it could be as simple as integrating new colourways in silhouettes you already wear on a daily basis.”

That said, it’s still easier to pull off oxblood if you dress them down a touch; Derbies are a more versatile choice than Oxfords because, while they won’t work with your smartest suits, you can wear them with everything from navy tailoring to jeans and chinos. That said, if you live in suits, a pair of burnished, oxblood Oxfords, with a Berluti-style patina, can be a distinctive way to make them feel more varied. They’re particularly good for making your workwear wedding-ready.

Casual styles offer much more leeway. The oxblood penny loaferis a classic and can be your summer go-to with anything from light-wash denim to tan, navy and even colourful chinos. Ditch the socks and cuff the hems for a Dickie-Greenleaf-on-the-Riviera feel.

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