I think that they look adorable with the plaid, II don't think they would work with a plain skirt. Somehow the plaid adds something funky to the outfit

You have lost a lot of weight, Kyle! You are disappearing. Wow. Impressive. AND you’re blonde again. Nice!

*spanner* I do not prefer the look of these particular ankle boots with a short skirt and tights. I feel that this look needs a heeled ankle boot/bootie and a pointier toe. As long as your leg line is, it’s not flattering. Black hose will help and so will a longer skirt, but I doubt the look to be ideal. Does that make sense, or do you disagree?

Angie: I do not disagree...I know something is off about this. Trouble is, I have a vision of wearing a short, "tough" boot,without much heel, with a more feminine skirt. What's the best way to make that work...or can it work? I know people wear Doc Martens with skirts, and those can be short and "tough." What's the secret, dear Angie?
(I've only lost 8 or 9 pounds).

Kyle, I was wondering the same thing. I have a pair of short boots similar to yours but have laces like the ones in the following picture. I paired them with flowy tunic, skinny belt and skinny jeans. I wonder if that would work?

http://www.polyvore.com/cgi/set?id=5665474

Kyle, I have nothing of substance to add except to say that you are looking absolutely stunning. Congrats on the weight loss - 8-9 pounds is a lot, you shouldn't minimize your accomplishment!

Kyle, my take on how to make the look work when the boot is really short and flat is to pile on the sophistication.

The “tough girl boots with the feminine edge” look seems to work more easily when the boots are a little longer. Were you perhaps thinking of the satorialist shot that floated around this forum a few weeks ago? It was of a very young Asian lass with HECTIC short docs and a pretty dress.

Julia, I'm sure your outfit worked. You were wearing jeans and those boots work with jeans.