Sorry about the lighting in some of these - it's rainy and dark today.
I just received a pair of super comfortable New Balance leather sneakers in a tan that bookends my hair pretty well (note: my pics are closer to the real color than the Finds pic). I really love the way the shoes feel and I think they look JFE. But I'm not exactly sure how to best roll jeans (or other pants) to get the best proportions with these as they are a bit larger in scale to me. I also wonder what jeans should be on my shopping list for fall (I already have white/cream BR jeans that I didn't get a chance to try on with these). I'm thinking I need a new pair of dark jeans but not sure if I want straight, BF, distressed, skinny or what! I plan to wear booties, these leather sneakers, my navy leather sneakers (more streamlined than these).

Pic 2 - blue jeans in skinny and BF style with various roll options
Questions:
Are skinny jeans too small at the ankle to wear shoes that are a little big?
Do they look better in the second two images with jeans that have a bit more volume at the ankle?

Pic 1 - 3 variations on tops/toppers and roll or not roll on gray straight jeans

I didn't spend a lot of time styling these outfits but wanted to just show some things that I thought would give a representation of how I might wear these without giving too much thought.

Questions:
Roll or don't roll? Are these outfits proportionately okay? Do you have suggestions on what length of tops/toppers, volume of tops, etc. that would be best with them?

I also tried to tuck the laces but there is probably a whole tutorial on how to do that properly so I'll have to read up.

Any help/suggestions greatly appreciated!

Edit - reversed pics for better display on forum

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