Thank you so much for your response. I actually did go to J Jill this weekend (there's one 45 min away) and I tried on clothes. I'm in medium in some tops, still large in a couple of their "lines" that were small in the upper arms, but tried on a small linen sleeveless top that almost fit already. I knew that they run large, but I still can't wrap my mind around the thought of buying size small or even x-small! The smallest weight I remember being is 145 and that was 18 years ago so those sizes don't even translate to today's sizes.
I'm going to order smalls and a couple x-smalls in the styles I know run large. I just need to get a few things somewhat cheaply so that I don't get hit with needing a warm weather wardrobe all at once. Even if I don't get to goal before the trip, I know I will before next summer - I'm never giving up