A gentleman’s guide to style with summer shoes

What’s the difference between a loafer and a moccasin? Where does the chukka boot originate from? And why is a penny loafer called a penny loafer? Puzzle no more with our informative guide to men’s shoes for summer.

Flip-flops and sandals
Flip-flop. The very name just makes you want to slump down on a sun lounger, with an ice cold beer by your side.

The term comes from the sound of slapping between your foot sole and the floor but the concept originated with the Ancient Egyptians when flip-flops were usually made from papyrus and palm leaves. (Did you know the toe strap was positioned differently by the various ancient civilizations? The Romans used the second toe, the Greeks the big toe, and the Mesopotamians the third toe.) After World War II, American soldiers brought the Japanese ‘zori’ back as a souvenir. The rest is history.

It’s always worth buying men’s flip flops or sandals in leather because they mould with the foot and allow it to breathe even on the hottest of days, after you’ve coolly emerged from the pool or sea, Daniel Craig style. But – and it’s a big but – there are two fashion faux pas to avoid. First, never wear men’s sandals with a suit to work. Second, never ever wear leather sandals with socks. Trim those tootsies to be summer-ready, and even treat yourself to a pedicure if you’re not afraid to show your softer David Beckham side.

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Slip on shoes were mainly worn indoors until the 1920s and the men’s loafer is rumoured to have several origins.

Many believe that men’s loafers originate from moccasins: traditional North American footwear. The word referred to a shoe with a puckered u-shaped ‘vamp’ over the instep. Styles varied according to the different tribes and some were so distinctive that you could tell the wearer’s tribe by the footprints. Moccasins hug the foot snugly, while their flat soles and soft leather create comfort.

Stateside, the loafer is held in high esteem as part of a classic business look. In Britain, a suede loafer is granted a more casual air yet is still eminently more stylish than a sneaker. For a relaxed yet suave approach, pair with chinos or jeans and a sports jacket.

However, a moccasin should not be mistaken for a dress loafer. It’s a less casual loafer made in the same shape as lace-up Oxfords but with elasticated sides so that they’re easy to slip off. This type of loafer is a little more formal and a perfect choice for a summer evening out.

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Penny loafers
And then we also have men’s penny loafers, created by GH Bass in 1936 by using a leather strip with a diamond shape cut out across the front. The penny loafer was originally known as the Weejun, the name of flat slip-on shoes worn by Norwegian farmers.

People started putting dimes in to the cutouts, in case of having to make a call from a phone box, then, in the fifties, American students used to insert a penny into the slit of the leather loafer – hence the name. When this loafer became worn by the likes of James Dean and JF Kennedy, its popularity grew and grew.

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Driving shoes
Men’s driving shoes combine luxury and practicality and are more Italian in heritage than their moccasin cousin.

Driving shoes are characterised by a distinctive pimpling or nubbed tread on the soles which makes them more durable when you’re in your sports cars and needing greater feel of the pedals – and the clutch if you’re a true sports car fanatic.

Originally, the driving shoe was very high end in status as it was only worn by men who could afford to buy shoes just for driving (with a high-spec convertible to match). But, when Italians started wearing them with suits, the driving shoe became the epitome of effortless style and dropped several gears from high speed to lazy cruising.

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Chukka boots
One day, it’s sunny; the next, it’s tipping down. Sometimes, it’s both. The Great British weather is often not very great at all. For those un-summer days, you need a back up such as a pair of men’s chukka boots.

Usually made from suede, chukka boots traditionally have three eyelets, a rounded toe and a thinner sole than a walking boot. They were first worn by British soldiers after playing polo because of their extreme comfort, and one of the earliest high profile wearings was by the Duke of Windsor on a trip to the US in 1924.

The desert boot is a variation of the chukka boot. It was standard issue in the World War II desert campaign so that British forces had rubber soles for better traction and could keep the sand out of their socks. And this fact, folks, neatly leads us back to reinforcing the point about never having sandy socks in the first place by never wearing socks with sandals.

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Enjoy the summer!