Ella, I think that is a really good idea to take a friend shopping with you and have her complete the transaction for you. I read echoes of myself in what you wrote. I hate to shop for clothes and wear what I own into the ground. I wear the same few things over and over to work each day, and wear them way past their "looking good" life.
I think for me it may be tied to being a hoarder. I accummulate all sorts of stuff and junk at home and have trouble throwing it out. It stacks up in piles. I read somewhere that this tendency is genetic and inherited. It had value in times of famine and poverty but not so much in times of plenty. But I am stuck with it. It is a struggle for me to deal with it. Recently I bought a dozen pairs of panties online because my ones at home were full of holes and I couldn't bear to go shopping in person. I am trying to get better and throw out old stuff with holes in it and that is ratty looking. Same goes for potholders and towels in the kitchen and bathroom. My teenage daughter is currently wearing some of the "vintage" clothes I wore in college because I never threw them away. They have just sat there in boxes. She loves the clothes, but how many people save clothes for 20 years?
Anyway, just wanted to let you know I sympathize with your struggle. Keep trying! Ask a friend for help.
Oh, and welcome to PC!