Short skirts are pretty much my go to look- I'd say about 80/ 90% of the time -I like the fact my style stands out from the crowd & as long as the rest of my body's well covered, feeling the cold against my legs doesn't bother me. Most of the time I'll be wearing sweaters or long sleeved blouses, boots & when it's cold I'll be layered up- coat, scarf etc. The only time I really wear anything revealing on the rest of my body is in summer when it gets hot- I've got a birthmark on my upper arm which is noticeable so I'm not really a fan of sleeveless tops.
When I was younger I used to be more uncomfortable with short skirts. When I was about 11 or 12 my legs really started growing & I found it hard to get trousers which were a good fit so just wore skirts most of the time. I wore tights at first so I was fine with most of my skirts being short but kept getting skin irritation from wearing them constantly so I ended up wearing skirts with bare legs by default. I remember being self conscious about my legs through most of secondary school even though I tried to act more confident plus a lot of the time they were freezing, even with knee high socks on & it took me years before I'd say I was fully comfortable with it.