Thanks for your replies - very helpful!
Jeneva, The sneakers aren't mine yet (not worn out of the house) but they are awfully comfortable and actually look better IRL (color wise) than the image shows. They *do* however remind me a bit of the "old folks", which is why I have not worn them out and still may return them. I was just throwing that out there as a very different take on the outfit wondering if that part would work. I do have sandals in nude but this is a cold weather outfit. I've been shopping for taupe desert boot style shoes but nothing has worked out yet and they also are such a different vibe.
Firecracker - I love your unconventional suggestion of a cap but really I only wear hats to hike and I would just feel strange wearing one any other time.
I may have to just learn to love the black booties I have as this is the only way I seem to be able to wear my black moto jacket successfully.
Slip on sneakers in leather would be great (for me) but I haven't found a pair to work for me yet. Many of them have the same "old folks" vibe to me as those tan sneakers.
Shoes are my nemesis.