Imagine if you had ankles that were extremely shaped, well beyond any such labels such as "cankles" - as in, your ankles were wider in circumference than your thighs.
In such a case, you probably would not want to show off your ankles but a flare trouser might be your friend. Because the flare adds in structure, giving a deliberate and intentional leg shape to your thighs, while hiding away your ankles. You'd choose a flare that just skims your ankles and nobody would be the wiser.
Now apply the same principle but in reverse.
If the clothes you wear are intentionally baggier/looser because that is the trend, say boyfriend jeans, then cuffing to show off your ankles gives you structure. There is a normal leg underneath all this bagginess. Your baggy jeans are totally intentional. You're so okay with your legs, you can swathe them in bagginess. And yeah, the baggier your jeans, the slimmer and daintier your ankles are going to look, in comparison.
My legs and ankles aren't my issue but my tummy sure is (apple shape) so I learned this principle long ago: Loose flowing top, hides my midsection while baring my arms. My arms aren't that great and I wasted so many years trying to cover them up, but with this strategy they look pretty good in comparison.
