Wow, that is really impressive Bella. I don't know if I could be as disciplined as you are. How fab that you found a tailor you trust!
My goals will come in phases. The first phase, which will probably take up most of October, is to get my fall wardrobe as much in shape as possible before moving. After I move, I won't have the same kind of expendable income I have now, so it's crucial I get all the big ticket items out of the way now (footwear mostly).
The second phase will be sorting out closet space. Honestly, I am REALLY stressed out about this. I'm going to be crammed in a tiny studio apartment and I have no idea how I'm going to house all of my clothes and shoes. I don't have a huge wardrobe, but I don't have a tiny one either. I use an entire room just to air dry my laundry each week. Much as I despise the idea, I'm probably going to have to take advantage of a dry cleaner, because I doubt I'll have room to dry all of my clothes flat and iron them.
It makes me sick to think that I'll probably have to get rid of a lot of pieces I like and want to keep, but I think that will probably end up being the case. It's troublesome that the first phase of my fall goals are directly at odds with the second phase, and I need to find a way to reconcile that.
The third phase is learning how to create rich, layered, unexpected, textural looks--despite what will probably end up being a small wardrobe. It's going to be tough. Sigh.