Jeans tend to fit me fairly well throughout but in those two areas I still have a hard time finding a pair that fit perfectly. This often means that I will be forced to customize these jeans to work for me. I have three major pairs of shoes that I wear with jeans my converse chucks, black dress loafers and flip flops. Often times if I go with jean that already has a boot cut fit they work for the loafers but I end up dragging my heel under the other shoes. Sometimes this can give you a nice distressed look to the heel of your jean, but on a rainy day it just means frozen feet and disgusting muddy heels on your jeans.
My simple answer is to go with a boot fit jean that doesn’t drag under my heel to much. Then cut the cuffs of the jeans vertically along the inside and outside seam to open the boot cut up further. This cut will look odd at first but after a few washings it will look nice and distressed and ad some personality to your jeans. The other answer is to cut the heel of your jeans out. Be careful when you do this and always cut on the side of caution. Once you cut the fabric away it cannot be put back. This cut will also look strange at first but after washing the jeans it will start to develop a nice distressed look. I always think it is better to cut your jeans specifically to what you needs are. Take the time to decide how to alter your jeans to make the work better for you next time you are looking to buy a pair.