Well, I have a different opinion on things that could look "dated" I have several statement pieces and obviously they're not something I could regularly wear, but I tend to wear them perhaps once or twice a year and I like them that much that I honestly don't care they look old or from several seasons back. It all comes back to personal style and taste, but then, what you said about practicality, I think that's a heavy con, if you don't usually do with large scale bags (and yes the men's "Small" PB is a large briefcase-like bag) then it's not meant to be, I don't know if you're short and petite, in my case I'm not a tall guy, even perhaps below average but I love both my PBs and I don't think they overwhelm my frame, then again, for a woman, the size probably isn't that easily fitting.I suppose it runs the risk of looking dated quickly, but I really like everything about it - the colors, the graphic, the leather. I wish I had a use for a large bag - I would grab that last pre-order! - but it's really too big for me.
The only thing I can tell you is that, the universe is quite clear in it's language, if you know deep inside that bag won't work, no worries, the universe has something even better in store (well not quite literally and not right now, haha) for you. Perhaps in the upcoming seasons they'll release a women's PB similarly styled as that one, who knows.