10 Ways to Wear Ankle Boots | Cuffed | When wearing jeans with booties, an exposed ankle is key to keeping your ankles looking as slim as possible. One of the ways to create this gap between the jeans and boots is a cuffed hem. Tip #3. Try this look with a longer pair of skinny jeans, rather than an ankle length pair. A larger cuff (2-3 inches tall) is more flattering).