Four Essential Pairs of Casual Shoes and Trainers

The four pairs of casual shoes and trainers that every man should have in his wardrobe:

Converse Chuck Taylor All-Stars

Thanks to the creative genius and salesmanship of former basketball player Chuck Taylor, Converse All-Stars (pictured above) are probably the most popular and easily recognised sports shoes in the world today. They’re simple, comfortable, come in a dizzying array of colours, and they’re cheap.

Avoid the wacky colour combinations and limited editions: buy a pair of canvas All-Stars in light grey or white.

Adidas Sambas

Originally designed for playing football on icy ground, Adidas have sold more 35 million pairs of Sambas since their release in 1950.

There are many, many different models of Samba, and you’ll often see them in cult films: Ewan McGregor wore Samba Supers in “Trainspotting”, while Owen Wilson wore Samba Ks in “You, Me and Dupree”. For a classic look that won’t go out of style, I recommend a pair of Samba Classic Ms, in black. The chaps at GQ maintain that black Adidas Sambas are the only trainers you can wear with a suit, though I’m yet to be convinced: suits need proper shoes!

Sperry Top-Siders

It is said that sailor Paul Sperry, sick of slipping on wet boat decking, was inspired to create the now legendary non-slip soles of Top-Sider boat shoes by his cocker spaniel. There’s some debate as to whether Sperry’s dog sat him down one day and said, “Look old boy, I have a wonderful idea for a pair of boat shoes. Have you got a pencil?” or whether Sperry simply noticed that the grooves of his dog’s paws provided exceptional grip on wet surfaces. I think it was probably the latter.

The overall design of Sperry Top-Sider boat shoes has remained largely unchanged for decades, save for a sprinkling of (occasionally insane) new fabrics and colours. I recommend either brown or navy leather. If you’re going to wear socks, make sure they’re of the invisible, loafer-sock variety.

Clark’s Originals Desert Boots

For me the name Clarks is inextricably linked with school. Every August, towards the end of the summer holidays, I would be dragged to one of Clark’s shoe shops for a new pair of clunky black lace-ups. It wasn’t until last year that I came across the distinctly more stylish Clark’s Originals Desert Boots. I tried some on, and was so happy with their fit and appearance that I bought a pair on the spot.

First released in 1950, Clark’s Desert Boots were inspired by the Egyptian-made military chukka boots worn by British soldiers in Africa during the Second World War. Crepe soles and soft suede uppers make desert boots almost as comfortable as slippers, though unlike slippers they look great with either jeans or khakis. Just ask Steve McQueen:

As for colours and fabrics, keep them simple. Forget the Harris Tweed limited editions and go for a pair of brown suede ones.

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