It's hard for you to look anything but great in anything, I think. But I might say ixnay on the bags. But only because I think there is more fabness out there.
If you like gray, I think it may be that you would steer toward warm grays/medium charcoal and not silvery. I agree that the light bag reads pretty "cool". The thing about reptile prints is, there are so many color variations, I'm just sure there's one out there that will bridge your color range better. Gray and taupe and black mix, or something, so it's light enough to pop a bit against dark tones and dark enough to be an accent for your taupes. That's what I would look for on my computer monitor while "shopping".
I think the black tote is pretty big on you. Again, if you have a definite purpose and think the tote has cool features, maybe yes. As in, do you carry legal size files or overnight stuff. But, black totes come in all materials/price points and so if you can identify a range of dimensions that is a better size for you, then you can search for those features. A tote in a just- large-enough size is one you are likely to carry more often.
I'm struck by how wonderful you look in those taupe-y outfits compared to black or very dark colors. Have you tried to identify the "taupology" of the color situation, and is the theme the color, or the level of saturation, or what, and have you been able to translate that to your other neutrals and accent colors? I had a color epiphany of sorts ( I still need much more enlightenment ! ) when I realized that even though I have fairly dark brown hair and pale skin, the typical "winter" dark jewel tones wash me out, but just slightly more medium tones of the same colors look better. So color is complicated, as noted in the prior post on warm vs. cool and Summers and so on.
So, take that with a large shaker of salt, as that's all well and hypothetical, but you may feel it's hard to track these items down.