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Only when I'm going out to meet with others. And as long as my hair isn't a complete mess and my clothes look prresentable it's okay with me. I don't obsess over how good I look, as long as it's acceptable for the opccasion.
I probably don't care about my looks enough. It's not that I'm a total slob when I go out of the house, but I don't bother with dressing up in a nice outfit or putting on makeup unless I'm going somewhere special. Usually I just put on a pair of jeans, a t-shirt or tank to, brush my hair, and call it good.
When it comes to other people, tbh I hardly notice unless they're outfit is really unusual. And even then I don't really care. Usually.
I like to make sure I'm at least clean before I go out; apart from that, I don't really do all that much stuff. As for other people, what they look like isn't a determinant in whether I want to be friends with them. If they smell, on the other hand...