Definitely one of the best questions I ask myself when doing a closet purge.
I used to equate 'would I buy it now?' to 'do I need this?' but as I got older and purged more, I realized that the question became more about myself as a person and how the things I wouldn't buy, was a reflection of my evolving self.
When I decided that I would not buy tight clothing 'now', it was because I had grown out of the clubbing and partying part of my social life; when I decided I wouldn't buy the same sneakers 'now', it was because I was embracing adulthood.
Did everyone already figure this out? I feel like it should be obvious, but it wasn't for me.