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

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.

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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.

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"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.

Admittedly, he was prewar English, with that inflexible combination of stylishness and stinginess that makes it a crime to look less than well put-together but a greater one to spend any money achieving this effect. He was also pre-feminist.

I have no desire to return to that dull state, but I envy the simplicity of his podiatric self-definition. His shoes had to be nothing more than he was: well-made, stylish and useful. I still hear the brisk cough of my father's horsehair brush early Sunday morning as he polished everyone's shoes in the mud room – the smucking pop of the Kiwi polish tin, that tempting turpentine smell. He made us feel new again.

Alas, a man can go mad today trying to win the trifecta of comfort, style and practicality in a single shoe, now that fashion trumps function. The marketing revolution began with sneakers, but these days, dress shoes are just as as bewildering and twice as treacherous.

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Most men I know wear no more than half the shoes they own; the rest are embarrassments. I once purchased two (two!) pairs of side-lacing (side-lacing!) casual shoes, one in sky-blue calf, the other in clay brown ("the potato-skin shoes," as they were known). I wore them for a week, but they sat reproachfully in my closet for 10 more years. Who did I think I could be? Elvis? William of Orange? A Bollywood star?

Shoe stores that once were stolid dens of respectability now come on like hookers on a bad corner. A pair of blades from Allen Edmonds, the American shoe retailer, was always expensive, but was wearable for decades. Not so much now. Back at home, contemplating my chukka-vs.-blucher problem, I surfed the Allen Edmonds website and was immediately confronted with the Norwich, a $345 monk-strap shoe.

Let me say this about monk-strap shoes: They are all the rage these days. They have been around for centuries. And they have never caught on. Why? Because they make you look like Cotton Mather, like a 14-year-old Puritan.

But according to the Allen Edmonds juiced-up website, the Norwich is "perfect for someone with a dynamic personality." (I wish merchants wouldn't make such claims: There are days when I am so in need of a dynamic personality, I might break down and buy them anyway.) The Norwich is "a testament to the Yankee strength of character." The prose is as inflated as a pre-race rundown in the Daily Racing Form.

And that's one of the more conservative tastemakers. Go more fashionable, and there is no hope for you. How about Mark McNairy's widely touted sunlight-yellow-and-Mediterranean-blue saddle shoes, perfect for those days when you want to resemble Bozo the Clown? Or Tom Ford's $550 espadrilles, which look like they were cobbled together by Cro-Magnon man?

Which reminds me: The oldest pair of leather shoes in existence date to 3500 BC, were unearthed in what is now Armenia, and look like a cross between a shrunken head and the open-toed boots waitresses used to wear in traditional Hungarian restaurants. The Greeks disdained shoes, but the Romans – the metalheads of history – venerated them. (They would have loved Fluevogs.) Side-laced shoes were first worn by students at Oxford University to protest against the knee-high jackboots of their fathers.

These details seem to matter. Men's wear is still mostly a uniform, after all: It's the details that reveal the man, that stand in for what the other gender calls intimacy.

To my surprise, every man I called for advice on my shoe problem was himself in the midst of a shoe crisis.

Matthew Hart, a writer I know, grew up in the aorta of Toronto WASPdom. He long ago eliminated the possibility of shoe regret by buying only two kinds of footwear: chronically expensive suede Tod's loafers for winter and Tevas, the Flintstonic sandals designed for life on a raft, for the rest of the year – even though he just moved to Manhattan from London.

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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