Coats/jackets.
I never seem to have just the right outerwear for the conditions I'm in. Then factor in how dressy I'm supposed to be, and I have too many damn coats/jackets. You've seen my commute. I walk 3 miles a day, so I need more than a jacket to just run to the car. If the jacket doesn't precisely match the weather, I'll be too hot, too cold, or too wet by the time I get there.
I have 7 in active rotation and 5 in reserves.