I'm still trying to wrap my head around the concept of ankle booties and how they can be styled. From my research, it seems like the most common use-cases are:

1) With dresses/skirts-
Best if matches skin color or hosiery/tight color and best with a heel (not great for MOTG) and shorter skirt (also not great for MOTG)

2) With shorts -
Looks best with shorter-length shorts, which I don't think I can pull off (very muscular thighs, ahem)

3) With pants, tucked into boot
I can't seem, to get this to work - I always get a "ballooning" of the pant around the top of the bootie. I like the tucked-into-tall boot look much better.

4) With pant, rolled over boots
Doesn't seem like I specifically need booties for this

So really, I'm not sure how to make these work for my lifestyle and whether they are worth investing in.

Does anyone have a good example of flat or almost flat bootie styling that would not be leg-stumpifying?