With recent conversations on closet editing, Bijou's post about keeping up to date, and the changing of the seasons, I'm considering how to wear my bootcuts in an updated way.

I'm really happy that bootcut jeans and trousers are trending because they happen to work well for me, provided I can find them with the right fit, length, and rise. But I have a few pairs of bootcut and flare jeans from years past that I'm ready to wear more this year, since the silhouette seems to be moving away from skinnies.

I'm wondering about the best way to update shoes and boots for a current look with bootcuts/flares. In the past I've worn them with heeled boots (generally pointed toe styles), which gives a nice long leg line and is traditionally flattering. But I'm not feeling my higher heels so much these days. I'm not giving them away -- just saving them more for evening or sitting occasions. I have a couple of lower heeled booties and cowboy boots with pointed toes, but is there some other shape/style I should be considering to update my boot collection this winter? I know that sneakers with bootcuts are a thing right now, and I'll have to try that even though I'm unsure of whether it will look trendy or just frumpy on me. The Finds below are part of my F/W footwear collection, some of which seem to suit bootcut jeans, but others not so much. I don't see anything terribly different from what I own in the retail market right now as far as boots/booties, but I haven't really been looking actively. Any ideas?