Considering the simplicity of its form, there is a lot of variation to be found in the humble loafer, but each has its own appeal. The penny loafer, perfectly typified by those from CELINE HOMME or The Row, is the mainstay, defined by a flat, moccasin-like shape and a strip across the foot that could, in theory, hold a penny. The loafer is traditionally considered to sit at the more casual end of smart, but the right pair can be plenty smart enough. Insist on high-quality leather and well-made soles.

The definitive “smart” shoe, the Oxford is an icon of classic menswear and a safe haven in an often strange and unusual footwear landscape. Defined by its “closed” lace eyelet tabs, which are stitched under the vamp (top) of the shoe, the Oxford is sleek and business-like, which is why it looks best alongside equally slick and business-like tailoring. You probably wouldn’t wear a black Oxford with jeans, but you can find Oxfords in suede or with brogue detailing if you want something that’s a little more adaptable to casual dress.

Very much the Oxford’s chilled-out sibling, the Derby is defined by its open lacing, which might only sound like a tiny difference, but gives the shoe a whole different vibe. Derbies, in general, are chunkier than Oxfords and are often fitted with cleated or even rubber crepe soles, but they’re still a polished option, as demonstrated by the likes of Dunhill and Edward Green. Wear yours with tailored separates or retro-skewed suiting. Or even with jeans and a blazer – a combo for which the Derby seems to have been destined to complement.

The smartest of all the many boot shapes, the Chelsea boot is generally defined by an elongated, almost pointed shape, a gentle heel and a laceless, slip-on ankle that’s often fitted with some form of elastic strip. Aesthetically, it kind of sits somewhere between an Oxford and a loafer – especially if you opt for classic Chelseas by brands such as Church’s or Loro Piana. However, a trend for steeper heels and more dramatic shapes has recently zoomed into view. If that appeals, look for boots by TOM FORD, Valentino Garavani and other purveyors of sartorial melodrama.

Who needs laces when you have buckles? The monk strap is a proper master-of-the-universe, tycoon-core kind of shoe, but its nuances may have been under-appreciated. It has the sleekness of an Oxford and the attitude of a boot. And now, that a series of brilliant shoemakers, including our own Mr P., have reimagined it on a chunky sole, it has the requisite heft to be worn with denim, too. The classic, narrow shape is still a winner, though, and looks especially strong beneath classic tailoring. Or, of course, a Wall Street-ready pinstripe power suit.