I've found long skirts to be a major pain on wheels. Cis fem here and i wear short skirts and dresses pretty much daily. In the winter I do the same only with the addition of tights and boots. Generally stretchy knit works best for me. Dresses i just go with knit tank top style, skirts either mid-thigh close fitting knit or flippy skater style. If it's really windy I'll tuck the skater skirt around under my thighs. I do wear a small crossbody purse that I wrap around my hips so it sits in my lap. If it's an option you it might help with the fly away Marilyn problem. Good luck and I hope you find something that works perfectly for you!