Frockspiration: Do you tote two bags to work?

Source: Street Peeper

I love it when fashion trends and practicality converge. Why it's taken women so long to acknowledge that you just CAN'T stuff all the books, planners, gadgets, makeup and shoes you need into one bag without crippling yourself is beyond me.

Living without a car has left me taking the MTR and hiking up Lan Kwai Fong with my usual beloved satchel bags slung around me and a Roo-Shopper bag with my lunch, flats (if I suspect my shoes aren't going to carry me through the day), umbrella and Kindle.

So far, I tell myself it works because pretty as the Roo-Shopper is, it's clearly "not a part of my outfit" since it looks like a grocery bag. But what if we were to acknowledge these poor second bags and make them a part of our look?

Since I'm never giving up my satchel's I'm on the lookout for a boxy square-ish tote (so it looks utilitarian and tidy). I want it to either be square or taller than it is wide and certainly not wider than my satchels I haven't decided yet if a fun print or a formal brown leather-look is called for - so perhaps both? =P

So do you girls tote two bags? And what's your favourite pairing?

Update: If the size is right, this is kinda what I'm looking for!