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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 ...

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.

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.

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