The word "あざとい" in this turns out to be quite interesting, with lots of loaded meaning and nuance. It doesn't seem to lend itself well to dictionary definition, or translate well in a concise way, but for the skirt here, this should be close enough.
Cute Satania ringsCute cardiganHugeCute smug faceAlluring miniskirt
So あざとい seems to be a pretty loaded word. The dictionary definition seems to be "calculating, clever, pushy, aggressive unscrupulous, etc" which doesn't make a ton of sense for a skirt. I found this article though, that goes in pretty deep detail to the word's meaning with respect to women and style, etc.
For clothes, it has the nuance of "showy" or "alluring", (e.g. exposing a lot of skin or body shape, or being frilly).
For women, it has the nuance of being outwardly flirty, assertive, direct, attentive, etc, but often with negative undertones of being inwardly calculating and clever, but in a quite possibly deceptive way. Physically it's associated with distinctive individualistic styles, like twin-tails and short bobbed hair.
I'm not sure we have a great word in English that encapsulates this idea well.
