My most anticipated sound became the ringing of the doorbell. It meant the UPS man was here, or the FedEx man, or the DHL man, bringing the goods.

I received a package at least every other day and sometimes two or three or four. Because I ordered so much, I often forgot what was inside them.

For a period of roughly two and a half years, until my wife permanently returned home from Abu Dhabi, I received a package at least every other day and sometimes two or three or four. Because I ordered so much, I often forgot what was inside them. It added to the drama and the ritual: the slice of the Swiss Army knife down the spine of the cardboard box and then the quick cuts along each side, the greedy pulling out of the paper stuffing, the annoyance of having to unzip the inevitable garment bag because it took too much fucking time, and then holding the item aloft on its hanger with thrill and titillation.

The only clothing I ever tried on before buying it was from Gucci. But many of the online purchases were fantastic—the patent leather trench coat from Burberry, a cropped leather jacket from Versace, a brown leather jacket from Ralph Lauren, a studded leather jacket from Cavalli, boots from Jimmy Choo, leather gloves from Ines in Amsterdam and Madova in Florence. I bought dozens of stretch jeans and leather leggings and leather pants that sculpted my lower body the way I wanted, with no room for speculation. I bought dozens of leather gloves that actually did fit like a glove. I bought dozens of boots, some with a flat or low heel that any man can wear, some with five-inch heels that only a man with real balls could wear.

Lisa in general liked the rocker look. But there were times I was too outrageous for her taste, and she began to feel like she was living with a hoarder. The kids liked the flair, maybe, but there were times they seemed embarrassed, or simply stunned. My friends, particularly those from Philadelphia, were appalled and confused and amused. With the exception of Lisa, nobody had any real idea of the extent of my addiction.

Too many of the purchases were sheer compulsiveness multiplying into more compulsion like split atoms. I bought an orange leather motorcycle jacket and matching orange leather pants from Alexander McQueen that made me look, well, very, very orange. The same went for a blue ensemble that made me look, well, very, very blue. I bought dozens upon dozens of leather jackets—bolero-style, waist-length, above the knee, below the knee—in which the gradations of difference were microscopic. I bought a pair of knee-length Stuart Weitzman boots and then two weeks later bought the exact same pair because I had forgotten I bought the first pair. I bought at least a dozen items that cost over $5,000 each but did not fit, the hazard of online purchasing, since sizing by high-end retailers is often like Pin the Tail on the Donkey. I bought items I wore once, or never wore at all, the tags still hanging from the collar. Yet I returned very little: The more the closets in the house filled, the more discerning I became, the more expensive the items, the more I got off on what I had amassed.

It is day three of the trip. I am at the Gucci store in Milan on the bottom floor. I am going through book upon book of sample swaths to be fitted for a custom-made suit. I stop in the middle to take an espresso to sustain energy and regroup, like halftime at a football game. I settle on a pattern made partly of silk.

I stand in front of the three-way mirror wearing a mock-up and am fastidiously measured by one of Gucci's finest experts on tailoring. A second person assists him. Both of them step back for perspective. This is why Italians should run the world.

I am taken back to an earlier moment in my life when I stood in front of mirrors at Brooks Brothers on 44th and Madison in New York. I was a preadolescent, pimples and early pubic hair, looking at myself with mystery as I tried on the khakis my mother had selected: two sizes too big so they would last longer than a year, since much to her disappointment, I was still growing. Combined with the billowing Brooks Brothers button-down in style back then, I was all set to sail, with my clothes as the sail. It was the preppy look that most of my friends wore. I fit in because I did not have the courage not to fit in, and the look was only accentuated when I went to Andover, ready at that point to equip a three-masted schooner.