Maybe just Michael Kors Hamiltons Large NS for workdays and Zanellato Postinas and Rabeanco for weekends and play. But wait those are exactly the only bags I use now.
Hermès Birkin 35 (for daytime)
Hermès Kelly 28 in box leather (for nights out to the theatre or dinners)
Hermès Lindy 26 (for casual dates/cinema dates)
Hermès Jigé or Kelly Pochette (for going out for drinks)