how about telling us how you dress for work? very formal as opposed to semi formal or even smart casual? cos i attach a different 'logic' to each style, and i genuinely feel that the proportion or style of the bag should be taken into consideration in a whole ensemble.
w/o considering the clothes, i'd say the Work is just chic. i wear my Work with dresses of slim cut cos i don't like to look too feminine. like shoes, the bag does make or break a look. jmho.
the Day to me is the most casual of the 3 styles. it's like a hobo, so it goes better with 'flowy' clothes... hope i make sense :shame: the colour of the bag also affects the image. eg a tannish colour is just more casual than a red or black one.
so, to conclude, the Brief is really more suitable as a workbag. it's more structured, giving off a more no-nonsense image than the other 2 styles. don't want to go too deep into this with my anal logic. i try to be as objective as i can. i apply this to all bags, not just bbags.