The first logo I remember was a white circle on Keds sneakers. Or maybe it was the Levi's patch on a pair of jeans.
I don't wear advertising, but I do own several things that have logos on them. I do free-lance work for a company. At one point the company got really fine jackets for its employees. It had the decency to send a jacket to me. Touched the cockles of my heart. I wear the jacket not because my cockles were touched but because it's a terrific jacket for the fall. And it has lots of pockets. It's got a small, tasteful logo on the upper left front.
When I was sailing in Maine, I needed a hat. One of the locals gave me a painter's (house painter) visor with some kind of local advertising on it. I kept it and wear it once in a great while.
My only other logoed bit of apparel is my Yankees cap, which I wear when the Yankees are in the World Series. It hasn't been on my head in a while.