
As a rule it is best to roll the hem twice, with the width of one one and a half inches. Keep it mess; a roll that's too flat and neat looks contrived. With slim-cut jeans, I love a single fold that is two and a half inches wide for a 50's beatnik look. Or you can roll it twice and keep the cuff thin.
Rolling the pants means you don't need to hem them, so you have a lot of flexibility with flats and heels. For a tomboy look, try oxfords; for a dressier spin, wear heels. But no wedges- they are too clunky.
To show off the skinniest part of your ankle, roll the pants to about four or five inches above the ankle bone. But if you're self-conscious about thick ankles, this look might not be for you.
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