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What Gryffin said about the "not quite right" placeholder. It could be any category (e.g. jeans, footwear, a top) but it is something that is essential to me and I can't find the version of it I really want and need so I take something hoping it will do -- and it doesn't. Sigh.
Dresses. Definitely dresses. I never had that problem when I worked in an office, but working from home, wow. The few dresses I do have I wear over pants and love the look, but for me, dresses are something I just don't even look at anymore. A non-item on my shopping list.
Shoes. Do I pass on those that are four or five hour shoes?
Jeans. My toughest place to fit is my backside. I try not to look (too much) but finding jeans that don’t wrinkle in back is nearly impossible. Also finding jeans loose enough in the calves.
Things I buy for a future need almost always are a mistake. Items purchased for an upcoming trip, or things purchased for a future dress occasion are rarely winners. I think I buy something "good enough" or something to fill what I think my need will be down the road so that I'm prepared, and it's never anything I'm truly in love with. I need to stop doing this!