I think it fits in with naming trends today, just as
Maisie and
Milly do.
If I was going to use it, I'd decide definitely which meaning I was going with -
Jessie as a form of
Janet or
Jean (as traditionally in Scotland) or as a feminisation of
Jesse. In my case, a version of Janet/Jean wins hands down. I like the historical legacy, and the other option seems forced to me.