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Words by Mr Peter Henderson

Unlike women's shoes, which deal in extremes of aesthetics and discomfort, men's footwear has always been rooted in dependable, classic styles: brogues, loafers, monk straps and evening slippers, to name just a few. That's not to say your choice of shoes has to be limited, though, because brands from Gucci to Yves Saint Laurent are experts at putting a contemporary spin on the classic styles, giving them a different look and feel while retaining their wardrobe-staple credentials. Click through the gallery above to see five of our favourite classic shoe styles, each with a corresponding updated version, for those times when you feel like putting a more adventurous foot forward.