Hey friend!
For skirts: honestly,what works best for me for clothing that doesn't conform to agab is to go for stuff that has the measurements written out. Get a tape measure and figure out the narrowest circumference around your belly. That's your waist. Then the widest circumference around your hips. Depending on where you want your skirt to sit, the waist band size should be between those two measurements. I find that bottoms sit better when they're only tight in one place, such as a circle or pleated skirt vs a pencil one. Maybe that'll be different for you if you don't mind revealing your hip shape! Also, just go to second hand shops (I remember some good ones from Edinburgh, though I've only been there to visit a friend), and try, try, try things on.