I agree with Ginger and La Pedestrienne. I think it just has to do with what kind of a look you are wanting and what you find appealing.
The looseness of these boots strikes me as very boho. To my eye, loose boots look best when contrasted or anchored with a fitted ankle, and both these pics show a more fitted ankle. The look isn't appealing to me personally because I tend toward tailored, classic looks, not boho. But I could see others wearing those shapes quite happily--in fact I regularly see young college gals wearing this combo/shape.
Personal preference plays a big part in what we like and don't like since we all have our own proportion and flattery goals. So Alaskagirl, for example, does not like the look at all on herself (and calls it a flowerpot) because she isn't fond of highlighting her slim ankles alone. But you'll notice that she does love wearing knee high stompy boots, which even though they are bulky do not focus the visual weight just on her ankles. So the stompy boots fit within her proportion and flattery parameters. On the forum, some members use flowerpot as a shorthand way to describe a particular fit, usually where a person's style isn't in sync with the looser boot's feel.
