The biggest change I've made to my culling process is to ditch anything that doesn't fit perfectly and can't be tailored to do so.
This floral shirt above was a sweet find from the Gap Outlet in Estero, Florida. I love everything about it, except for the fact that its one size too small and the arms always ride up around the shoulders. I wore it one last time last week, then added it to the Salvation Army pile when my suspicions were reconfirmed.
These are the Gap City Flats. They look kind of weird, right? They are in the test phase. I love how small they fold up and the relative comfort for travel, but they look funny.
Part two of my new culling process is to make a plan to replace any of the items I got rid of with new versions that fit or look better. For example, I got rid of this chambray shirt because it was too big and couldn't be tailored not to ride up. I just need to find a replacement. I still want a pair of cognac/taupe/neutral flats, but the ones above may not be it for the long-term.
Here are the rules I've been following to clean house:
1) If conditions apply to the piece (can only wear with this shirt underneath or with that cardigan), get rid of it
2) If the fit isn't perfect, pitch it. Find someone else it flatters or give it away
3) If you don't reach for it on a regular basis during the season, sayonara
4) Forget about what you paid, the great deal you got or how you were convinced this was the perfect piece for you. Learn and move on...to the Salvation Army
5) Be 100% honest
6) Get rid of duplicates or anything remotely similar, especially more novelty/specialty pieces
I've found that by getting rid of the excess, I can see all the pieces I really like, unconditionally.