Plushpenguin, this looks like a bootcut to me. I think you're going to have to commit to a heel height. You can also buy two pairs of the same jean, and have them hemmed two different lengths for two different heel heights.
What my local jeans place does is ask you to take the jeans home, and wash and dry them a few times (yes in the dryer - even if you don't ever plan to put them in the dryer, it's a good idea to do it a few times *just in case* somebody in your family is feeling generous someday and does the laundry for you... hee hee).
Then you come back in with all the shoes you think you might want to wear them with. They start with the highest heel and while you are standing tall, they put a pin in the back of the leg, just slightly above the floor. That is where they hem it, so it doesn't drag on the floor but is nearly all the way there. You can then try it on with other heel heights and see how it works. I believe Angie has said it's okay if they drag with flats and get worn at the edges... it's a "look"... however too much drag, in my experience, means a risk of tripping over oneself.
Patience, for 14" don't you mean you *don't* want to go shorter? I have my straight legs and skinnies hemmed long, so they scrunch up a little, with both flats and heels. Hmm, I guess if you are always going to tuck into boots, then you'd want them shorter though. With flats and heels, I think they look cute with some scrunch.
That's the nice thing about straight legs and skinnies... you can get away with a much greater variety of shoe heights, I think. Hem for the highest pair, and then scrunch with the lower pairs including flats.
