I have a number of skirts and dresses in the wardrobe and have to encourage myself to take the slight effort of choosing to wear them.
I am a chunky pear shape with sturdy legs. I have a few tips which might help other reluctant skirt wearers of a similar shape.
This means in the winter it is sensible for me to buy tights in size XL in the suitable dark colours I will wear - black, dark brown, dark grey, navy. It is also useful to have tall leather boots which fit my calves. I find I wear the ones with a low heel the most, and some benefit from a cushion innersole. The best skirts and dresses for winter hit just below the knee and a either straight or flared.
In summer I prefer a longer length skirt which hits at the bottom of my full calf, comfortable but slightly dressy sandals and a culotte under skirt for comfort. When shorts would be appropriate it is more flattering for me to wear a travel skirt with a silk culotte slip and walking sandals, though these days I do also wear long bermuda shorts despite having rather lumpy knees.