Well, I have to say, as a former plus-size woman, I used to avoid buying clothes because I couldn't bear to go into a store and try anything on. There was a period of time where if I needed something I'd literally just go into a store and buy whatever was on clearance and looked tent-like enough to fit me! Occasionally I actually saw something I liked tried it on, felt good about myself, only to catch a glimpse of myself a few days later in a glass door or soemthing and feel humiliated by what i really looked like. Frequently I'd just appropriate something or other of my husband's, but there was nothing like style or anything that flatterd me and boosted my confidence. It was a sad period of time in my life.
I did keep a box of old clothes from high schoo. I don't know if what I felt was hope, but it was wishful, desperate thinking. When I was at my heaviest I truly couldn't visualize myself as thin person. Hiring a stylist, or even asking for advice on dressing a body I hated would have been deeply embarrassing to me.
After I figured out my weight issues (not an easy fix, to be sure) I had two pregnancies. The first pregnancy occurred midway into my big weight loss, so my pre-pregnancy clothes were too big after that baby was born. At the time I became pregnant for the second time I weighed somewhere between 140 and 150. I kept those clothes, and by the time my baby turned about a year old I fit into most of them again.