Can Pricey Shoes Boost a Man’s Ego

IT’S BEEN AWHILE, but I still recall certain agonizing aspects of my first big job interview. Barely in my 20s, I was living in Sydney, Australia, and going for an editor position at a publishing company that specialized in luxury fashion magazines. I was a working-class kid with big ideas and an expanding bank account, thanks to the proceeds from a boy band I’d fronted (long story), and I’d made it to the last round. It was time to meet the owner, an intimidatingly suave Italian who was, by all accounts, a walking sandwich board for Milan élan.

My outfit from that day remains a blur, but I vividly remember that as I was strategizing my look, it dawned on me that the reasonably handsome pair of oxfords I planned to wear—my only real special-occasion shoes—just weren’t going to cut it.

The Paul Simon song “Diamonds on the Soles of Her Shoes” was big then, and perhaps the lyric about the poor boy who splashes on after-shave “to compensate for his ordinary shoes” had insinuated itself into my consciousness. To be clear, it’s not like I grew up with a “shoe fund” like the cash-strapped family on “The Waltons.” My parents were hardworking first-generation immigrants who made sure we never went without anything—and to my thinking I was always an aristocrat of the mind. But I also knew that not too many kids like me ended up with great jobs in the media. Before you could say “class complex,” I high-tailed it to the most august shoe store in town to drop a small fortune on a pair of brown lace-up cordovan derbies from Crockett & Jones.

I hastily wore the austere, leather-soled beauties straight out of the shop, and so began my decades-long love affair with—how else to put it?—a better class of shoe.When it comes to masculine connoisseurship, some guys obsess over cars and cigars, others are into mechanical watches, but fine shoes are my compulsion. Don’t get me wrong: I love sneakers as much as the next guy, and I’ve been known to splurge on ridiculously trendy footwear (I call these “high-earning hairdresser shoes”). But for the most part I’m partial to Church’s, John Lobb, Berluti, Ferragamo and Alden—establishment brands whose sober styles are the staples of international business.

For someone who works in fashion, I detest shopping and assiduously avoid clothing stores, preferring to buy online and have my shirts and suits made by New York tailor Paul Marlow. But I could spend hours at Jeffery-West and Leffot, shops on Christopher Street in Manhattan, poring over footwear from redoubtable names like Edward Green, Gaziano & Girling and Saint Crispin’s. I am fascinated by the shoes’ smell and sheen, by their provenance and supreme detailing.

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