For the most part, I try not to purchase anything that is expensive, too polished, or dressy. This is hard since my cousin is getting married next month. Due to my transition, I am not too keen on spending a lot of money on a dress that I won't be able to fit in a year (you can only take in clothing so much). So I focus on pants primarily and nice, cheap tops.
Right now drawstring pants are my friends. As I go down dress sizes, I can still wear my drawstring pants even if I drop down two additional sizes. So that helps. I might even purchase few drawstring skirts for some variety. My tops are another story. I have to be careful with those. I need tops that are more relaxed in fit. If I buy one that fits too close to the body, when it gets loose, it will begin to look sloppy. I do not want that.
I know that I will hit my goal before I know it. Once there I am treating myself to a shopping extravaganza! That is something for me to look forward to. Keeping my eye on the prize(s)... I will get to be fashionably chic again!