Like any story of recovery and redemption, mine begins with a moment of clarity. I had been set up on a date. She was smart, with cute freckles, but it was clear from the first margarita that we had little in common. She lived uptown and went for guys who worked at Goldman; I had tattoos and wrote for GQ. Still, enough tequila can persuade two horny people to put aside their differences for a night.

In the morning, I awoke to find her standing over the bed, putting on her clothes in what appeared to be a race against time. “What's up?” I rolled over and asked, not entirely shocked she was running for the hills but disappointed we wouldn't at least have a morning canoodle. She fastened the hook on her bra, threw a blouse over her body, and kissed me on the forehead. I think there was pity in her voice when she told me she was leaving.

“By the way,” she said, “how do you have more clothes than any girl I know—and no TV?”

After the door slammed behind her, I looked around my studio apartment in the unforgiving morning light—at the hulking dresser stacked with folded dress shirts still in the plastic they came in; at the coat rack sagging under the weight of parkas, windbreakers, jean jackets, raincoats, and overcoats; at the ziggurat of boots, sneakers, and brogues stacked knee-high on the floor. Then there was my double-wide closet—stuffed with an auxiliary cache of shoes, plus more suits and sport coats than a Hollywood leading man could wear in a lifetime.

Uptown Girl was right: I had a problem. But she couldn't have known how deep it went, couldn't have known what clothes had come to mean to me—or what, on every level, they were hiding.

I have no family history of sartorial excess. I grew up in Maine, where “style” means Elmer Fudd hats with earflaps. My mother still dresses like she would have at Woodstock—flowing tunics and flared jeans. Dad? He kept to a strict uniform—L.L.Bean khakis, a blue blazer, and sockless Sperrys. My stepmother, like a Tenenbaum, never left her tennis warm-ups. In school, I simply chose from what I saw at the mall: Gap, Structure, and Abercrombie.

And then on the morning of September 11, 2005, a few years after I'd left the nest, my recently divorced father walked onto the Piscataqua River Bridge and jumped. I didn't consciously grieve his suicide through fashion. But a death so sudden leaves a hole. And holes like that take so long to fill that you don't always realize what you're stuffing in there to fill the void. You're not self-aware enough to even comprehend what you're doing to soothe yourself. To distract yourself. To make you feel good about yourself. To project okay-ness to the world when what you feel is anything but okay.

Shortly after the memorial service, I moved in with a girlfriend. Before landing in New York, we lived for a while in her parents' house in Greenwich, Connecticut. Her father was a prominent executive, poised and dashing. I'd sometimes find myself wandering through the closets in their home, admiring his collection of custom wool suits, trousers tailored to brush the tops of his polished Berluti shoes, his dress shirts sewn with a simple monogram: PTG. I had my Daisy Buchanan moment, sobbing among the shirts in that house. How could they all be so beautiful?

One sunny morning, the day after Thanksgiving, he drove me from Greenwich into Manhattan until we alighted on Paul Stuart, the Waspy enclave on Madison Avenue. This was to be the day he bought me some proper clothes. In the mahogany dressing room, when a tailor slipped a perfectly cut jacket onto my shoulders and I stepped up to the mirror, the confusion of the past few months melted away. I didn't have a father, but I had a father figure. And I had a suit of armor made from the purest cashmere.

Clothes soon became my fixation. I spent hours on Scott Schuman's newly launched street-style blog, The Sartorialist, studying lo-res images of peacocking men in Milan. I wanted to be one of them—or all of them. I took a corporate real estate job that I despised, but that enabled my habit, affording me entire paychecks' worth of suits, ties, and shoes, allowing me to masquerade as a Master of the Universe.

In 2007, I spent no less than $25,000 at Paul Stuart. Every salesperson knew me by name. In time the hangovers from these sprees began to hurt; the shame leaked in. I began hiding my purchases, leaving them in my car, running garment bags into our apartment under cover of darkness or while my girlfriend walked the dog. When she'd catch me, I'd feel foolish. “Didn't you just buy a new suit?” she'd ask. I had. One with lavender pinstripes. When had I become Oscar Wilde?

I needed help. I quit the corporate job, the girlfriend quit me, and I left New York for a while. But I still had all those clothes and a strong sense of denial. And it would get worse.

In 2011, I landed any menswear junkie's dream gig here at GQ, covering the style beat for our then fledgling website. A real-life menswear blogger. I could talk pick stitches and raw hems and cutaway collars, reference looks from the Dior Homme runway, name-check the best places to score vintage in Tokyo. For me, clothes were a drug, and I was getting high on my own supply. If Marie Kondo had seen my monthly haul of size mediums, she'd have stroked out. Not to mention the reissued sunglasses. Rare selvage sneakers. Watches. White jeans, blue jeans, brown jeans, black jeans.

And then I had that date.

I spent the morning in bed awed by my revelation: Clothes had become totems of my pain, and it took a meaningless hookup for me to see that they were suffocating me. I quickly realized that any solution would require drastic measures. So I undertook a project I referred to as The Purge, a complete fashion transfusion—everything must go—designed to rebuild my wardrobe, and by extension myself, from scratch.

Preparing for The Purge required genuine soul-searching. I had to admit that I wasn't Steve McQueen, Lou Reed, Miles Davis, or any of the other menswear heroes I blogged about. I'd never be PTG or the Milanese men in their tortoiseshell specs and peak lapels. I was me. Still wounded, but healing. Still interested in style, but growing out of the need to flaunt. If I was honest with myself, I didn't even want these clothes anymore.