I always have a work bag in addition to my purse. For me, it's not about the number but how the work bag is shaped (different from the purse), and if it's functional for my job. I think it would look silly if you carried, say, two Sabrinas, or a Sabrina and a hobo of some sort because both are obviously purses. But I wouldn't think twice about carrying a Julianne in addition to another purse, because without the cross body strap, the Julianne looks like a work tote. Sometimes when I need a change of clothes I carry a duffle in addition to my purse, other times when I have lots of meetings, I'll carry a tote for the paperwork, or whatever I need. So all that to say, I think it's fine as long as the work bag is functional for what you do and not too similar to the purse.