So my true waist is 26.5", right below the ribcage, obviously I wouldn't wear my denim this high. My low cut (inch or two below navel) measurement is 29"... I'm not sure which I should size down from, can anyone provide insight?
Lol. I think you mean "hip" and "waist."
What jeans are you thinking about buying first? Without that information we can't help you with sizing down / sizing up / staying true to size.