I bought 3 pairs of new shorts this year to replenish a collection that was getting old. I generally prefer dark colors, wear them a lot in the heat of summer as a casual look, usually with a T and flat sandals or sneakers. I don't "dress them up" much although I'd like to try that this year.
I'm petite, a curvy pear with fairly big thighs. Like pants, I usually find that regular sizes fit better than petites because I also have a fairly big derriere, but I do need a moderate to slightly low rise. I generally go with classic bermudas. I find the 8 or 9" length is best. It hits just above my knee so it covers most of my thigh but leaves enough knee showing so that there is the illusion of a bit of length to my legs. I have also learned that there HAS TO BE a bit of a taper to the legs, slimmer at the knee than the thigh, for 2 reasons. 1) if they don't taper, they ride up on the inseam when I walk and 2) if they don't taper just the right amount they make me look wider. I have altered shorts in the past to get that taper just right, although I didn't have to do it with any of these new ones.
The ANA ones (black and olive) are 98% cotton and may not have terrific longevity (like many JCP brands) but they fit really well, as do the Levis.