When to donate?

This evening I went out to dinner with a group of my friends and I wore these very cute wedge high heels (3 or 4") .  I remembered they were hard to walk in, but since I haven't worn them in a long time I wore them without question. They worked perfectly with the outfit. After dinner we did a little window shopping.  Why not? I then realized my shoes were way too heavy and I was having a hard time walking as fast as my friends.

Here's my question: when should you just give up and say: the shoes hurt, I'll donate them.

I think I should just give them up. They could be the best looking shoes ever, but if they hurt, they will always hurt. I'll wait for shoes that are great in every way. The ones that are amazing looking and I can wear them for hours. They exist but are just hard to find.

I've been trying to minimize my life with stuff. Fashion to me had become less about buying and more about the perfect fit. I want to love my purchases and wear them over and over again.  This makes writing this blog a little tougher.  I'm not going to the mall every weekend to buy the latest trends. However, I think it keeps my life a little more balanced.