Thanks, everyone!
Texstyle, I do generally like longer shorts, and sometimes roll them, but I have a hard time figuring out a good spot for them to end on my upper legs. Honestly, I struggle with shorts and I hate trying them on. They're right up there with swimsuits. They confuse me. Sometimes I think I look better in something that ends about halfway down my thigh because that seems to be a relatively narrow spot on my leg, and then I look at all the cellulite and think I should just stick with covering all the way down to or below the knee, but sometimes that proportion just doesn't look right. It seems to be hard to find anything in those longer lengths that isn't frumptastic, but admittedly, I haven't looked much.
Sizing up is something I'd consider, but it's a little tricky -- the ones here already stretch out over the course of the day (they're looser now than they were when I took these photos), so I'm not sure I want them bigger than they are. I'm not sure if baggy butt looks better or worse in shorts than it does in jeans.
But I'm glad you're making me think about all this. This year might be a good time to reevaluate my shorts and get some new ones. These and my other similar ones, all have those slash front pockets, which probably don't do me a lot of favors in the hip area. But it doesn't seem so easy to find anything without some kind of pocket bulk in a casual short. I've been wearing the same ones for the last three summers. They are pretty snooze-worthy, but all the cute shorts I see (patterns and such) are too short. My time for 3" inseams is long gone. Even a 5" inseam comes nowhere near the middle of my thigh. I think the ones I'm wearing here are 9". For BF shorts, I have some old, slightly too-large jeans I chopped off below the knee, and I roll them up a little bit. They're OK, but really, really casual.
I like shorts that are not tight, but also not so loose as to add a lot of volume. I love the idea of something lightweight and drapey, but anything like that I see is pleated, and I am not going there.
I guess you can tell, I just can't get excited about shorts for me. But it's just not feasible for me to wear skirts and dresses every day in the summer. I pulled out these shorts today and threw them on for this outfit, but I haven't taken a good hard look at my summer bottoms yet, so you've given me food for thought.