Cuffing jeans with dipped booties. "Since these boots have the dipped front, you don’t need your entire ankle to show to achieve your goal of elongating your legs. Just a small half circle peeking out is enough, as shown.
To make this look as effortless as possible, don't make your half cuffs match. Keep them about the same height, but roll/cuff them at slightly different angles and widths to make them look effortless and a little haphazard.
How To Wear Ankle Boots With Skinny Jeans: Option Another fun option is to just cuff the jeans once. If your jeans are too long, this won’t work – the cuff should be no more than 2 inches. Leave just an inch showing above the boot.
When wearing jeans with booties, an exposed ankle is key to keeping your ankles looking as slim as possible. Try this look with a longer pair of skinny jeans, rather than an ankle length pair. A larger cuff inches tall) is more flattering).