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(Deborah Baic/The Globe and Mail)
(Deborah Baic/The Globe and Mail)

What’s up with those men’s boots with the strap over top? Add to ...

The question

What’s a monkstrap?

The answer

It’s a slip-on shoe with, instead of laces, a strap that goes over the vamp, ending in a buckle on the outer side. Some have two straps and two buckles and are called double monkstraps. Sometimes they have a plain smooth toe, sometimes a toecap. They are currently in fashion, and being paired with the finest suits, in brown and black.

I am uneasy about the acceptance into polite society of this formerly nebbish marker of academic and European style. I have always found them mildly embarrassing, as if one is trying to advertise, by wearing them, that one speaks Esperanto or plays the sackbut in an amateur Early Music consort. I have always visualized them with corduroy trousers and a red cardigan and a bow-tie, and maybe quirky striped socks. In other words, perfectly acceptable and respectable, but not exactly what 007 wears when he enters the casino and the girl in the backless dress across the roulette table sizes him up as a trained killer. (And isn’t that, really, the ideal to which all men’s clothing aspires?)

The other thing about monkstraps is that they are not considered a formal shoe. They have in the past only been worn with sports jackets and trousers, not suits. Now stylists are sending models down the runway in these casual shoes and the soberest of three-piece grey pinstripe suits. The matchup has become fashionable, but it still looks awkward to me. Certainly, there are some suits that one can casualize – by wearing them with a T-shirt and, say, Chelsea boots – but they are generally not three-piece or pinstriped. I still think monkstraps look best with jeans and a tweed or canvas jacket. However, if you are the daring sort who wants to wear a slick pair with a weekend-evening suit, my favourites are the black ankle boots with a single narrow strap by Hermès.

Russell Smith is a novelist. His recent memoir, Blindsided, is available as a Kobo e-book. Have a fashion question? E-mail style@globeandmail.com.

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