Probably the best solution for updating undesirable career outfits is to give Players the option to edit career outfits in CAS. Many of my Sims whom I've decided they wear glasses and a hearing aid end up losing these accessories when they go to work. Pretty annoying. If I remember, customizing career outfits was possible in Sims 3.
It would be a welcomed update to allow editable career outfits, and with this change, maybe provide more career CAS unlocks for Players to decide how they want their Sims to look in their career. In the Painter career, for example, maybe a vintage smock from the Impressionist era, complete with a Van Gogh straw hat. Or an artistically painted suit jacket to show you've achieved maxed career level as a Painter.
