I ama man and I wear a skirt every day if I can but my wife only allows me to wear a skirt around the house at the moment. I have lots of skirts of various types and materials. From really short microskirts ( for her eyes only ) through minis to maxis. My wife says that I have good legs and look good in a skirt. During winter I wear thick tights with the skirt for warmth. All other clothes I wear are men's so I still want to look like a man even though I am wearing a skirt - I just wear normal clothes with a skirt instead of trousers.
Depends on the weather. When its hotter like it has been lately I'll wear them a majority of the week because I prefer them over shorts. They're usually mid thigh length to knee/above knee length, but I have a couple that are long ones.
It all depends on what I feel like doing that day. Sometimes I like to wear a short skirt if it's really hot, other times I may wear a long maxi skirt if I want to feel free and flowy yet cover up. It all kinda just depends on how I'm feeling that day and what fits my mood.
I don't wear skirts unless its at the beach or night and I'm going to a hang out/party. If I'm at a party, Ill wear a mini skirt, skin hugging skirt, the length will end at my fingers. If its at the beach, it will be a flowy skirt that begins at my waist and ends at my fingertips as well.
Like, 2 times a week (mostly because I have been spending all my holidays home). I like to wear medium skirts mostly (2 fingers above the knee), and I have been obsessed with maxi skirts recently, especially the ones who are longer in the back side.
I mostly wear jeans or skinny jeans day to day... I only wear skirts or dresses when it's very hot out or if I look particularly awesome that day. During the peak summer season, probably twice a week. I love wearing dresses and skirts during the fall, I think it looks more romantic.