I am going to be honest, I am writing this debate today for my own personal needs. I recently bought an adorable pair of black ankle boots and NONE of my jeans look good with them. I am aware the trend is to roll the jeans to the top of the boot as pictured, but these particular boots have a slant from the front to the back and I can not find a single way to roll my jeans to look good.
Just for my own curiosity, I tried just wearing my skinny jeans that were extra tight around the ankle without rolling and that looks bad as well. At this point I am tempted to give up and only wear them with tights and dresses but I felt like Friday Fashion Debate was the best place for my last chance at wearing them with jeans.
Maybe the problem is just the boots I chose. I looked at photo after photo and none of the ones I saw look like the ones I am discussing. So my instincts tell me to stick to a very specific type of ankle boot.
My second thought was that maybe it is the jeans I am wearing. I noticed a lot of the ones pictured are short and the roll is very small. I am slightly vertically challenged so my jeans always seem to be longer than I want but I don’t buy “short” jeans because then I can’t wear them with flats which is my go to shoe.
Help me out fashionistas! What are your suggestions??