How to master the slip-on style for a slick smart-casual look.

There are few shoe styles with as long and colourful a history as the loafer. Originally adopted by jet-setting mainland Europeans, who had noticed similar styles on Norwegian fisherman in the 1930s, loafers were later copied by the English and Americans, and became a casual shoe for the aristocracy, and a favourite among Ivy League colleges, who often wore them sockless for convenience (otherwise known as student laziness). Whether you plan to bare your ankles in a youthful fashion or adopt a more traditional, besocked style (no loud patterns, please), the knack lies in matching the attitude with the rest of your look – here we’ve gone for an outfit that’s on the smart side of smart-casual. Ready to embrace the slip-on shoe challenge? Here’s how to pull off loafers with confidence.

The penny loafer is the most versatile loafer a man can own, and a great choice if you’re looking to nail that tricky smart-casual dress code. This particular pair, from fine shoemaker John Lobb, is guaranteed to stay in style, with its rich chocolate suede and sturdy stacked heel. We recommend teaming them with chinos – such as this pair from Incotex. Finishing at the ankle, the trousers will leave just enough space between the top of the shoe to ensure you get the famed “gap” just right. Given that we’re approaching November, we’d suggest adding a pair of socks in this case, but, aesthetically speaking, you could do without if you’d prefer.

A happy medium on the scale of formality, Prada’s cotton-twill blazer can just as easily be dressed up as it can down. Its navy tone works well with everything, making it a fail-safe piece in any man’s wardrobe. Opt for a timeless pairing and wear it over Oliver Spencer’s light blue, tab-collar Oxford shirt for a polished smart-casual look.

No outfit is complete without considering the finishing touches, and nothing shows sartorial know-how like choosing accessories to complement your footwear. Looking for a bit of wrist action? We suggest opting for Braun’s BN0035 watch, which with its scratch-resistant lens and sleek stainless steel case, is more than suitable for withstanding everyday wear and tear. A brown leather belt, such as this handsome one from Polo Ralph Lauren will go very nicely with Braun’s stylish time-turner – and indeed the chocolate tone of the loafers – as the strap is a similar shade of chestnut brown.