If you like the Brief, why not look at RTT? It is similar-ish in shape just bigger, probably equivalent to a WE.
WE - I think GH makes it POP but it would probably be quite heavy since the bag, in itself is already quite huge.
I say try an Escapade! I have a Black GSH Escapade and I've had an RTT. The RTT is more feminine because of the top/closure, which is like a City or a Part time. The RTT closes like the Weekender, Work and Twiggy...Which is less structured and less feminine.