Yes, I forgot to pack an entire category of clothing. Not long after my arrival, I bought an emergency T-shirt from a local frozen-custard shop to get me through the trip.

I slipped on my T-shirt and sneakers, then swirled myself into my marshmallow fluff. My sister handed me a bouquet that she made herself after a weekend of YouTube watching.

I was wearing a light blue chambray shirt from J.Crew on the night I first met my wife. It was 2016, and I’d just turned 25. And, having bought the shirt with my first substantial freelance ...