I have a policy of comparing the value to me with the value to others.
Right now there are so much clothes being sent to the 2nd hand market, that they are basically worth nothing. So unless it is almost new and in perfect condition, if you like it and you wear it, you should keep it until it wears out!
A perfect example of this is my boots. In my perfect capsule dream I have one pair of black ankle boots (maybe a tan pair instead...but we´ll cross that bridge when we come to it).
Uggs, which are only good for winter and also only very casual wear.
2 pairs of tall boots, which again are only for winter wear.
And the future boots of my capsule wardrobe black ankle boots. They can be worn for more of the year (as they are less warm), they can be packed easier for travel (as they are smaller), they can be dressed up more (just because of their style) and they can be worn with more stuff (because of their colour).
So why do I have the other pairs?
I bought them all before i started on this sustainability journey, and by the time I got to doing the wardrobe cull, they were all well worn, I loved wearing them, and I knew that they wouldn't be worth much to anyone else, so I decided to keep them (and look after them) until they were worn out.
Getting rid of them would have meant that I got to capsule size quicker, but it wouldn't have been the most sustainable thing to do!
So basically my idea is, if there is something you have that you love to wear (even if you have 2 of them, or it isn't very versatile) if it wouldn't sell online or in a charity shop, because it is old, or worn, or was cheap to begin with, then wear it yourself until it is at the end of it's life...it will take longer to get the perfect wardrobe, but it is more sustainable to do it that way!