I don't pretend to have the answer to overcoming all of that...but something that has helped me find connection with some of the pieces in my closet is making them "mine". Of course a piece becomes mine when I purchase or take possession of it. It becomes my responsibility...my responsibility to care for, wear, repair, + pass on thoughtfully. What I mean here by "making it mine" is adapting the piece to my preferences.
Sometimes a piece speaks to me in shape, but not in every detail. Sometimes the proportions are a bit off for my frame, but I can see my way to making it work with a well-placed dart or a raised hem or some volume taken out. Once I have made these changes...picked the stitches + restitched them...looked closely at the craftsmanship + participated in it...I feel a deeper connection with the piece. It is often this connection that can inspire a commitment to increased use + wear.
Connection is a tricky beast. On one hand it can make us hold on to things that we don't need...but on the flip side of minimalism...when we have purged down to the essentials...we need to nurture connection again...so that we can stop the cycle of waste.
A large portion of the pieces in my closet have undergone some sort of alteration or embellishment. I think it enhances my connection.
P.S. Soundtrack playing in my mind for this post. :)