Thistle, I think this is a tough call for me.
Trotters can be very comfortable but they have that squared off toe and go frumpy fast. I ordered and returned some Trotters low wedge pumps this spring for that reason. Looked matronly on. I think these tend this way though, the reptile is nice. I have found an almond toe or rounded point to look better on my foot--you might try. Isn't "pointy-toe" trendy but seems fairly classic and can be comfortable.
The cutout vamp in the second shoe looks prettier on your foot, but if not comfortable, keep looking, but maybe another smoking slipper would work--there is a huge number out there now with a lot of variation in vamp, toe taper and so on. If for dresses, I would love to see you in a nude color for lower contrast, which to me helps the frumpy factor in low-heeled, higher vamp shoes. Pants OTOH are a lot more forgiving for various loafer styles.
Number 3--I'm not sold on the tiger pattern but then that's just me. For the style, are you planning for pants or dresses? I think that style could be fab with pants but I'm having trouble finding the right look for skirts and dresses, myself, which is killing me because there is a good comfort factor there in tie shoes.
Please take my comments with a large spoon of salt, because I have something of a poison eye for a lot of modern footwear with dresses, which is why I don't have any, or much, and am struggling. It might help to show them styled in some outfits.