How often do you purchase the chicest booties, yet never wear them because you are questing how to pair them with jeans? First start with your jean! Jeans are long so they can fit people of all heights... they are intended to be taken up. For those of you who have no desire to go to the seamstress, designers created the ankle skinny just for you! Below I have paired one jean (Rag & Bone Skinny-La Paz) with four booties of all heights. Two styles I always go with is tucking the jean or rolling it up. But remember if the jean is not hitting right below or at your ankle bone, it will not look right. If you are tucking your jean into a boot, you do not want a lot of extra fabric or it will be bunchy. If you love the roll look, I like to flip the bottom up 2" or flip it up twice with each roll at 1". I have styled the same bootie both ways below for the visualist out there!