To me it just looks like someone trying to get in on a trend that was in no way designed for his body type. He looks like a large athletic man crammed into pants designed for a very thin person.
I'm not a huge fan of that ankle exposure look, but it looks especially bad in a shoe with a significant heal. The slightly higher pant leg came into fashion, when people were exposing their socks, which looks good if not overdone. With the bare skin it's weird. With a shoe with a heal and straps, it's even weirder.
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