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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 ...

But when I called, he, too, had just purchased a pair of chukka boots, made by Rockport in dark-brown suede for $149, that he planned to wear at all times, even with a suit. I admired his insouciance. “I suggest you will increase your chances of hitting the admittedly small sweet spot shared by age and fashion,” he said, “if you keep in mind one idea: dark-brown suede.”

Eventually, I called my brother. I usually do. His name is Tim. He works in Manhattan as a stockbroker. “Today, I’m wearing my penny loafers,” he told me. “They have not one but two holes in the soles.” He owns seven pairs of shoes: two pairs of lace-ups (one black, one cordovan), two pairs of loafers (one black, one cordovan), two pairs of sneakers and a pair of trail runners.

He, too, had been cruising shoe stores, gathering a sense of the terrifying choice that is out there. “I want to be more fashionable,” he explained, “but I don’t want to look like a 56-year-old dink trying to look younger. But I also don’t want to look like one of those guys who dress to look old-fashioned. In other words, I’m having a style crisis. I want a conservative but modern look. I want a look that says I’ve been around, but that I’m gonna be around for a while yet. And I want my shoes to say the same thing.”

A lot to ask of footwear. I recognized the symptoms.

“Why don’t you just go modern – long in the vamp, pointy toe?” I imagined a pinguid calfskin half-boot in black.

“I had those loafers, remember?” he replied. And I did. I will never forget them. He was an embarrassment to walk with, a man on two runways. “I looked like a platypus. I was trying to look like everyone else.” He was in his 30s then. “You think you’re being avant-garde, but then you wear them twice, and you think, I look like an idiot.

“What about dark-brown suede?” I said. “I hear you can’t go wrong there.”

“New York is all about the brown-suede brogue at the moment,” he said, sighing. “Every guy on the street is wearing them. It’s just” – he searched for the diplomatic word – “a little bit old-fashioned.”

I pointed out that this is what I wear a great deal of the time. I thought it spoke of permanence.

“There’s nothing wrong with permanence. But you have to remember that death is permanent too. You need to jazzercise that look.”

Perhaps I will, given the way shoes are trending. “What’s interesting about Western culture,” Elizabeth Semmelhack told me, “is that we are starting to shake off the shackles of Enlightenment thinking, without it threatening our notions of masculinity.”

Shoes have always been a symbol of independence, of a mind on its own path, which is why men take the purchase of a new pair so seriously, even if they pretend otherwise. Slaves liberated in the American Civil War were presented with new shoes to commemorate their freedom. And when people in the New Testament remove their shoes, they display their subservience.

I realize that it is possible to read too much into buying something to wear on your feet. But when you find a pair that speak to you, you might want to pay attention. I went back to the store, and now own those new brown boots and brown derbys. I feel as much like a girl as I do like Dad. But I have to say, I like it.

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