Okay, here's my bag-to-bag and computer-to-computer analysis.
Bags tested:
- Brookline (Laptop Pocket Dimensions: 14.5" W x 9" H x 1.4" D); and - OMG (Laptop Pocket Dimensions 13" W x 9.5" H x 1.4" D). The OG is bigger than the OMG, but has the same laptop pocket dimensions.
Computers tested:
- Dell Inspiron E6230 (12.2" W x 8.9" H x .97" D) with about an extra inch of battery attached on the height; and - MacBook Pro late 2011 (14.25" W x 9.82"H x 0.95" D)
Conclusions: Dell fits in both bags; MacBook Pro fits in Brookline (but is close to the limits width-wise on the OMG) but no fucking way for the OMG. Even sideways.
Sorry for not being clear -- long story short, the MBP absolutely does not fit in the OMG. Even when I turned it sidewise to see how it would fit that way (that's what the picture is of). It is close width-wise if you turn it sideways, but as you can see the height doesn't work.
I *think* the Brookline would fit a slightly bigger bag but you could always order and try it out? They have free returns. That's how I discovered that the OG is laughably big and the TT does not fit my MBP
With 2 zippers, I think you could lock it by stringing something between them and attaching a lock there. It could hold pc, lunch, and slide in another smaller pouch for purse-like stuff, then just add a gym bag.