Thanks for the detailed reply Penny! I haven’t tried Trees shorts but do have a few pair of sombrio. I’d say the sizing on the wild rye is similar to Sombrio, and stretchy, but they don’t bag out as much as I find the sombrio shorts do.
The waist on the Wild Rye is not stretchy, but the rest of the short is. So the waist is definitely the more key of the measurements. I found the waist fit generously so a person who’s waist is similar to smaller than their hips would be okay with the waist. For a body shape that is a larger waist and smaller hips, the measurement to base sizing on would be the waist!
Also I think your hair would look great with fun shorts :)