Clothes shopping, ughhh...!
Historically clothes were a big deal for me, or rather a big problem. As a teen I was paranoid that my clothes would look weird. However I was totally incapable of noticing what others were wearing, and as a result I insisted that new clothes were similar to the old ones that I was used to. I became proficient with sewing, in order to prolong the life of my clothes. These efforts actually made me look weird, as I was wearing old, outmoded and often worn out attire. When I had to get something new, it could not be "flashy", green, have any printings, and the front should look the same as the back (for shirts, sweaters, etc.). I got better with clothes when I moved away from my parents.
Nowadays I buy clothes when absolutely necessary, usually while doing other shopping, and I try to shop for one type of clothes at a time, in one store (except when a special event, such as an upcoming trip, necessitates more "emergency" shopping). T-shirts, underwear and socks do not cause me any trouble. The rest are "torture", as I am quite picky, need to buy exactly what I want, but can never find that, of course. The worst are shoes (for some reason it is very difficult to find men's 8 size). I've managed to dress somewhat more mainstream during last couple of years, or so I hope.