When evaluating keep and returns I try to consider how it works with the rest of my wardrobe, where will I wear it (is it for an imaginary life), is it unique to my wardrobe, does it meet a need/fill a hole, how does it work with my style goals, what will the likely cost per wear be, and so on. But the 'I love it!' voice is sometimes hard to hear over.
Another question that occurred to me today is, will I wear it at least 20 times over it's lifetime? I can buy items that are inexpensive and will have a low cost per wear even if worn 10 times, but outside of special event shopping, I've decided I want things that I'll hold onto for a minimum of 20 wears.
From tracking wears for over two years this isn't as easy as it initially looks. My wardrobe isn't minimalist although it's manageable for me, and for some things like non-black tights it might be kind of impossible to get there before they give up the ghost. Tops and skirts usually get there over 2-3 years. Shoes, jeans, coats and bags get there within a few months. I'm not sure if all my dresses will make it --which is why I only have 6. Very high happiness, but somewhat specialized, items might get there over 5-6 years.
I think it might be a good way to evaluate what it might be time to pass on ---if I've had it at least a year and 20 wears still seems like an uncomfortable stretch. Also what I really should return with tags on (like that gauzy pale blue off the shoulder peasant top, I just can't see wearing it 20 times.)
Do you keep a number like this in mind while you shop or evaluate when it's time to retire something? What do you think is a good number you'd like to aim for in terms of minimum wears per item?