I love wearing dresses but am most comfortable wearing long flowy hippy type skirts. Chiffron material is best, it feels so feminine.
However, when I get out there as a woman full time I can see myself wearing hiking leggings, walking trousers or jeans a lot as I'm an outdoorsy type of girl. Long skirts or short dresses just aren't practical for much of the time. I would consider tight shorts but if I'm on the fells where there is bracken and heather, ticks can be a problem with exposed legs, not to mention spiky gorse, thistles and stinging nettles!
If going shopping though it would be the skirt option all the way for me, I love the look.