Okay, so I've been on a buy-this-ugly-skirt-and-shorten-it-cute-like, a la Kara from Unusual Form. Her tutorial is by far the most thorough I've ever seen. While you may think, "I can figure out how to fold something shorter and sew it that way, why do I need her tutorial?" I agree with you but with vintage-y, lined skirts in fabrics like linen and wool, and where you really want to use a blind hem, who couldn't use a few pointers? And her results are so good and so consistent, it's worth a look even if you don't have a stack of skirts like me. (Skack? Okay, maybe that's going too far.) Anyway, go there and read. You'll be better for it.
So *ahem* back to me. I have pictures here of my first skirt to try this with. While I am not at all doubting whether to hack it shorter, I have to say that I liked the pictures I took of it long much more than I thought I would, especially with the mustard tee I randomly tried it on with. I'm going to document it like a normal outfit, but I must be clear: I did not wear this for a day. I know, your whole world revolves around knowing what I wore when and why, so I need to get this right.
Tee: Target. ($7) Skirt: Thrifted. ($1) Shoes: Thrifted. ($3)
This is about the proposed length. I know I need to decide exactly, but until I start experimenting by pinning it up and checking it out, I can only say I think it should be abouuuuuut knee length. (FEEL FREE to leave suggestions! For reference, I am 5'2". Little person size.) Oh, and did I mention this was part of that first 99cent Mondays trip I took? (Sorry I left the tag on for the pictures. That's a little weird.) It makes me feel good that even if I just royally screw up the whole project, almost nothing was lost.
So feel free also to leave comments nagging me about when you'll see the after pictures. I need some prodding with these things every once in a while.