Can I Wear Logos Without Them Wearing Me? An Investigation

I enjoy shopping alone, but I’m never truly alone. Inside my head, a chorus of critics—ranging from my accountant to Trinny and Susannah from the original British version of “What Not to Wear”—tends to weigh in on potential purchases. A few seasons back, it was my mother’s voice that piped up as I stood in the downtown Manhattan Balenciaga store, transfixed by a preppy-ish denim tote emblazoned with a retro-looking logo. “How tacky!” she said. “You don’t want to be a walking billboard.” In my childhood, she’d barred me from wearing logos and, as an adult, I found them kind of distasteful myself. Yet recently I’ve been...