Monk straps are based on a design that has been around since the beginning of time. Or at least the dark ages, or maybe medieval times. They are, in fact, derivative of the buckled shoes worn by monks. The monks, however, could only hope to wear something as elegant as the versions available today.
Although they are considered “casual,” The monk strap is actually a very practical “dress” shoe, in my opinion. The monk first gained popularity in the 1930’s and then caught on with service men, who wore them in polished brown calfskin with their class A uniforms. And, like all things “military” that have trickled down into the civilian world, the monk strap carries with it a bit of dash. Generally seen with a plain toe that contrasts with the rather sporty strap and buckle, the monk is a very easy shoe to dress up or down. The Churchill’s brown suede version has gained classic status and many fora members will argue that John Lobb’s Jermyn II model is the most sublimely elegant shoe that a man can own (although they may have ceased production of this model and replaced it with the Vale.) I think that with a bit of brio, the monk strap can be worn with a suit and tie, odd jacket and trousers or jeans and a blazer. The very definition of easy and elegant.
The trick to enduring style with the monk strap is to make sure that the toe isn’t too chunky or boxy, the styling is kept to a minimum and the whole is given to a “sleek” look. No chunky buckles, no tractor tread soles, no “distressing” (ever, for that matter.) Pictured above are R. Martegani’s answer to the monk shoe. The brand is affordable (well compared to Lobb, anyway, whose monks will set you back about $1,300 at the current exchange rates) and will soon be available on-line.