My biggest nightmares (well fashion wise!) are shoes and jeans!
As far as shoes go, I have I guess oddly shaped feet and can never ever find the right pair - too short, too narrow, right length but the feet slip out. I guess my feet are outliers in India and so I barely have choice, it it fits, the pair comes home with me
And I am still on the quest for that perfect pair of jeans!
I'm curious to understand what items of clothing or facets of fashion give you grief?