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(alannah cavanagh for the globe and mail)
(alannah cavanagh for the globe and mail)

Ian Brown's quest for the perfect shoe: Not such a straight-laced affair Add to ...

It’s hard to overestimate the ecstasy a man can feel upon finding the perfect shoe.

In the fall, as the old fiscal year turns red and flutters to the ground, as the temperature clinks down a register and we suddenly find ourselves pondering sober questions of the human autumn (will I be ready when the snows come?) – in the fall, men look into their closets, rake their eyes over their footwear, and think: Those brown suede brogues have really had it. They look like bald rats.

This is when you make your way downtown – through the swells in their narrow trousers and anteater brogues and the swellinas in their leopard-print everything and new winter boots – to buy a new pair of shoes.

Men struggle to stay calm as they do this. It’s true: Every fall, as Milan and London and Paris and New York show us what we won’t be wearing next spring, men spiral into shoe panic. This is the male version of the hot flash, and the shoe industry has no interest in it cooling.

The fog of foot fear hit me two Saturdays ago, a fall day as bright and brisk as clever conversation. So I hitched the dog and made my way along Toronto’s mile of mink.

In the first shoe store I entered, I saw what I instantly knew I wanted: a pair of chukka boots, ankle-high, three-eyelet lace-ups, deep brown, narrow last, leather not suede. And next to them, a pair of thick-soled bluchers, or derby shoes, also in brown.

(A derby laces up through opposing flanges of leather, each of which is sewn onto the upper of the shoe. An oxford ties through a single-piece upper, which is why oxfords are more concise, elegant and dressy. In fact, derbys were originally for weekends, never for the city. Neither were brogues: The perfing on brogues – the holes – were originally designed to drain water as one mucked across a Scottish bog.)

I asked the saleswoman if she could bring me my two choices in size 13. She had a graceful foot-side manner, as they say in shoebiz, but it didn’t help. A dizziness of indecision hit me. The bluchers (named for an 18th-century Prussian general) were perfect, but round-toed – what my wife calls “hamburger shoes,” and not as a compliment. The boots, on the other hand, were cool. Perhaps too cool, for a man my age.

I asked the clerk to put both pairs aside and said I would return the next day. Then I went home to have a stressful little think.

There was a time, before men were relegated to their current status as feckless domestic pets (see Hanna Rosin’s The End of Men, among others on the subject), when shopping for shoes did not induce a crisis of male identity. There were prescribed shoes for conscribed roles.

“Since the 17th century,” Elizabeth Semmelhack, the brilliant senior curator at the Bata Shoe Museum, explained to me, “there has been increased sensitivity to the idea that men don’t express their masculinity through fashion.” According to the philosophers of the Enlightenment, reason was all a lad needed to transcend his class – brains, not brogues. Men dressed alike for the next 250 years.

But feminism cracked that traditional male identity open the way a jackboot splits a walnut. As the roles open to men have proliferated, so have men’s shoe styles, beginning with the sneaker revolution in the second half of the 20th century. (There is a debate as to whether it was kicked off by Converse or by Jordans.) The wider the range of shoes men can buy, the more we wonder who we are. The relationship isn’t causal, but it’s more than a coincidence.

My father owned the same six pairs of shoes for 40 years: two pairs of brown oxfords (one a brogue wingtip), two pairs of black (ditto), sneakers (for squash) and loafers for the weekend. He also wore wellingtons and an older pair of brogues repurposed as gardening shoes.

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