I was using a MW Vandal for a while, which is great for winter because I tend to carry more stuff on my commute, but in warmer weather I just don't need that huge thing on my back. I looked into the Rambler for a smaller option, but one thing I don't like about the Vandal was the lack of small pockets for things like my wallet, or keys. I mean, it does have a couple small pockets, but they're slightly TOO small. So I looked into Chrome backpacks, but they all seem to have a round-ish burrito shape when packed with stuff, which I didn't like either.

Anyways, I generally don't like timbuk2 bags, the styling, but I found one of theirs that is pretty awesome. In actual use, it's probably the best backpack i've used. Laptop sleeve, tons of pockets, built in bottle opener. It might not fit your "looks cool" requirement, but for functionality, it's great.

http://www.timbuk2.com/tb2/products/...aptop-backpack