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I'm 40+ and jeans are my usual clothing at work or running errands. At home I often wear more slacky clothes. In winter or autumn at cold weather going to a store I may just put on winter jacket and trousers, that will hold the wind (not sure what you call them), and I don't really have to worry what I have underneath. As long as it's warm!
Usually dressing better means replacing jeans with something else, often trousers though, I rarely wear skirts or dresses.
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