I would wear skirts, I think, if they didn't require the sort of tops they do. One simply cannot wear a skirt on one's lower half and an oversized man's dress shirt on one's top half. Or even a baggy t-shirt, for that matter. Skirts require an upper garment that I am unwilling to wear, something close-fitting, usually rather revealing, and undeniably female. Unfortunate that that is the case, because I think ankle-length skirts in themselves are very comfortable and pretty, and also a good way to get ventilation around one's legs on warm days without revealing said legs, because revealing them would generally require shaving them, and all and all the whole situation of wearing any lower garment other than trousers is just too feminine for me.... Sigh. But I do wear them on less casual occasions. Although I have to borrow my mother's because I don't own any myself.