So...I should clarify. The 8 times-worn shooties were actually in my closet for about 3 years before I let them go. They were a dressier shoe and I knew they wouldn't get a lot of wear -- I just didn't anticipate how little. They fit nicely and felt great. But our weather made them hard to wear and when my hair went grey I let them go because the colour no longer worked so well in my wardrobe.
As for other items...I definitely hold onto seldom worn dressier items. I know when I buy them these things won't get a lot of wear, but I need them anyway. If they fit and look good, I keep them.
I'm much, much quicker to return items bought online now. If they don't feel right in my try-on sessions, for whatever reason, I send them back. Most things are cost-free to return, or I return them in-store, so it is free, or I swallow that cost because it is less than the cost of the item and having it around drags me down. I am lucky that I live in a big metropolitan area for now -- it does make in-store returns a lot easier. And the post office is four blocks away, for postal returns.
I tend to go with my gut feelings. If I love it when I put it on, I'll usually love it in the wearing -- although sometimes I can be fooled. Some things don't work out as well in comfort or in durability as we imagine they will. My Cons high-tops fall into that category -- and I duplicated!! (I did get considerable wear from both pairs but I expect to let them go at the end of the year.) Usually, I don't cut tags if I'm in doubt.
Here are some items I ordered online (or even bought in store), considered, and then returned -- for whatever reason. Just this year's. No doubt I'm forgetting some...and there will be more to come.