summer is easy-show some leg,how much depends on the look, weather, type of shoe etc. Roll pants, capris, jeans or whatever, or not is usually easy to decide. Everything seems to look great with sandals, flats, sneakers, booties, heels of all kinds be it sandals, wedges, or whatever.

Now comes fall and winter, and the what, how, socks, no socks, boot heights, and length and width of the pants, jeans, etc. gets to be a problem. I think that is why tall boots are so popular, just tuck in the skinnies and, or leggings and you are good to go. But with all the variations in shaft height of booties, heel heights, widths of pants and jeans, need for warmth by adding socks ,and not wanting to just roll and show bare leg, problems arise.

I am finding that my ankle booties are the biggest problem. Just analyzing my fall winter booties, I realize that I seldom wore my lower ones. somehow they just do not work for me unless I show some leg, even if it is just a little bit. do you think longer jeans that bunch look OK with the low ankle booties? What about skinnies that are just at ankle, with oxfords, sneakers, or other type flats? what I wore most and liked best are my booties that have about 5" shaft height, and fit tight around my leg. With ample calves, getting into higher shaft boots is a fitting problem though. Interested in comments, solutions, and your problems with this fall/ winter issue.