LOL I've been trying my darndest to get my MiL into some funkier clothes...but all 73 years of her conspire against me and she gets into those elasticated waists with the narrow ankle all the same...!
I have a similar story to Jasp's - DP saw a pair of jeans of mine I wore in my early 20's and laughed at them for being 'harry high pants'...ummm, these were the original low waist jeans before you could find them in every jeans outlet - my trusty Gas Station hipsters from 1996! Then hipsters got cut even further and now they should be called Crotchsters.
Definitely specialty underwear! I wear everything low (skirts a size up so that I get the style, but not sitting so high) so all I own are hipster undies.
I recall my friends rejoicing when high-waists were making the catwalks two years ago - where did those styles go?
TD - you might like the clothes at the Wind and Water Designs website (google). Shorts with a higher waist And made in Brisbane - email the lady, she'll take in extra details to match you to a style or size. I've got her Grace Pants, and they are the only pair of higher waisted pants I have but that is completely offset by the maddest flare ever!