Help Needed - Just recently came back to the Sims

Hi everyone! I recently came back to the Sims after some years and decided to start a Legacy challenge by working on a save file. I've been building houses, and including some families, some of them of my own and some from the galerie. I've been working on a Pietro Boselli simlike, but I'm unable to just quite get it. So, I've been wondering if someone with good CAS skills could lend me a helping hand with this sim.

Thank you all in advance, and excuse my bad English (it is not my first language)