Wishful thinking, peut-etre, but I'm not yet convinced that those of us who aren't blessed with the lean-and-leggy gene have to sit on the sidelines when it comes to wearing ankle boots with skirts. From the New York Times Style section, I lifted a few photos that help provide some hints as to what might work and what pitfalls to avoid.
First, what seems to work:
Note the darker skirt and hose/tights, and that the boots fit pretty narrowly at the ankle.
Here's one that some might find intruiging, but just seems wrong to me. Aside from years of having "never wear shoes that are lighter than your legwear" drummed into my brain, the lighter boot seems to blend in too much with the pavement, making it look like her leg is cut off at the ankle. Those boots would be really cute with jeans, though.
And here are a couple that IMO just don't work. On the first, the wide opening at the top and the cuff draw the eye horizontally which shortens the leg. On the second, the light coat creates a giant block of color that interrupts the vertical line. And what's with the white contrast on those boots? Ugh.
Once my orthopedist has cleared me for takeoff (to get out of my loafers and back into a little heel), I'm going to lend my body to science and try this for myself, and I'll share my findings.