What is the difference between these two?

I ask because my DH and I were people watching this weekend, and we were wondering. He does not like this look - he pointed out that it makes even tall women look stumpy. We saw a woman, for example, who was probably 5'10 and tottering around the city streets in 4-inch heels and short-shorts. (Kind of a ridiculous outfit for a cobblestone street, but I digress). Her shoes went up around her ankles and managed to stumpify her legs - despite being heels and her legs being so long. I think if they had been nude instead of black, it would've worked better.

I do like the look - well, I think it is the cage heel that appeals to me more than gladiator - but I may be mixing the two up, hence my initial question. I just don't know how anyone pulls it off, with shorts/clams/skirts/dresses. What is the secret?