I've seriously read through this thread solo many times and have had such a hard time coming up with an answer. I'm not at all conservative with my wardrobe, nor was I at my heaviest (think too much leopard print :O). Due to my shape (rectangle/inverted triangle/whatever) I've always carried little weight in my arms/legs so I'm not afraid of shorts/tanks. I'm close enough to goal that I can more easily find my style of clothing in my size.
But I think I've figured it out - at this point what I really want is to be comfortable with my waist/stomach. So I really just want to wear a friggen bikini or sports bra or something that shows or highlights that area. Cliche? Perhaps. But I just wanna know what it feels like to not be hiding that dirty little secret of a lumpy-stretchmarked tummy I've always known.