I bought all new clothes at the beginning of transition because I had all F clothes. Tossed everything, including socks and underwear. Well, the useable stuff went to Goodwill.
After a year on T I had lost a fair amount of weight, so bought some new clothes. Also, some of the clothes I wore early in transition had negative connotations for me, so I ditched those.
Now I've lost even more weight and have purchased a few new things.
I haven't bought anything pricey like a suit or nice shoes or anything, as I've been waiting for an occasion to do so, so as not to out grow it or shrink before I can wear it. Do most of my shopping at Walmart, Target, or Kohls, so saves money.
Jay