Should I shave my head?

I've been thinking about it for months and I just recently bleached my hair but I still have it on my mind. I'm curious if I could pull it off and not look like a potato or just generally ugly. Most of the time I dont wear makeup as I dont have time. I'm overweight but currently trying to lose it so I worry about that as well. I dont ever really do my hair, I have curly hair so I wear it down for maybe 10 min and then throw it up into a bun. I need honest opinions and wont get hurt by any answers. I know I'm overweight and I know I have a rounder face but this has just been lingering for months, my husband and boss have both said it's ok as well.

Thank you ladies

Pictures to show my face shape and general appearance both posed and just sitting here