I am always boggled by the people who do things like shave (it's not even mostly a principle thing at this point, just I'm way too lazy), do stuff to their hair, and own make-up, but think skirts are hard.
Ya'll actually vaguely femmey women must have a very different concept of what skirts are, because skirts are what I wear when I'm *not* putting in any effort. I have a collection of mid-calf to ankle length skirts that are wide enough to sit cross-legged in, and mostly have pockets. They are the best thing in the world. They're comfortable, they're easy to adapt to the weather with layers - I agree with the above about running shorts, tights, and knee socks, and if the skirt's long enough you can even get away with sweatpants - they're femme-y and don't read as baggy/slouchy, and yet concealing enough that I don't really have to worry at all about how I look under them (+1 much less likely to stain if I'm spotting), and the same skirt can be either super casual or semiformal business wear, depending on whether I wear it with a t-shirt and work boots or Mary Janes and a nice jacket.
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Ya'll actually vaguely femmey women must have a very different concept of what skirts are, because skirts are what I wear when I'm *not* putting in any effort. I have a collection of mid-calf to ankle length skirts that are wide enough to sit cross-legged in, and mostly have pockets. They are the best thing in the world. They're comfortable, they're easy to adapt to the weather with layers - I agree with the above about running shorts, tights, and knee socks, and if the skirt's long enough you can even get away with sweatpants - they're femme-y and don't read as baggy/slouchy, and yet concealing enough that I don't really have to worry at all about how I look under them (+1 much less likely to stain if I'm spotting), and the same skirt can be either super casual or semiformal business wear, depending on whether I wear it with a t-shirt and work boots or Mary Janes and a nice jacket.