One of the side effects of having a smallish clothes budget and not adding that many items each year, is that I'm not great at culling. What's more, thanks to YLF and my natural antipathy to buying, I don't have much that I don't like.
But things still do wear out, and I've just culled 5 pairs of shoes that were really past it and in some cases about to physically break. In all cases, I've had replacements for them for a while, that I've actually been wearing but needed to make sure worked.
I another brave and uncharacteristic move for me, I just got rid of several pairs of handed down PJs I was given last winter. I hated them, and they were too big on me, but I couldn't cope with the idea of buying new ones. Now I'll be forced to (or keep wearing tracky pants to bed, which I don't mind that much).
I have to say that the whole issue of when something is worn enough to discard is a bit fraught for me. Love to hear your thoughts on this.