I think I might have a problem with this.

I recently cleaned out a bunch of shoes and outerwear. Today it was rainy and unseasonably warm. I got dressed to go to the gym and then realized that the black NF fleece-lined hooded jacket I would have normally worn was in the laundry. (Because a bird pooped on me on my way home from work the other morning, but that's another sad story.) I ended up wearing my J Crew field mechanic jacket which was fine, weather-wise, but it felt a little silly over my sleeveless gym shirt and cropped tights. I was kinda regretting the bunch of hoodies I got rid of because "I always wear the NF anyway."

Similarly, I haven't needed a business casual wardrobe since 2012 and have gotten rid of almost all of those clothes. Which was a bit of a problem the last time I had to unexpectedly attend a winter funeral and ended up in black patent leather ballet flats when there was snow on the ground, because they were the only dressy footwear I still had that went with the only dressy black pants I had left.

Does anyone else struggle with this? Do you get rid of things that you hardly wear, only to discover that hardly doesn't mean never?