based on your vans size id say 43, but based on your red wing size id say 42. Kinda weird how the sizing varies that much, do you have any uk sizes in there? for reference, im a 9 in vans and red wings and 42 in cp.
^looks kinda sloppy where the jeans hit your shoes. You can probably hem 1.5-2inches (and still do a single cuff), especially if you're gonna be wearing them with non-sneakers. 2 would probably be better since you really need to sag little judging by how nut-hugging they are in the first pic.