Hey:
I'm a new switcher (or rather, will be switcher once my new PB arrives), and I've been going nuts to find a bag solution that will fit the bill. I'm kinda a bag freak, so I've done a bit more research than one probably should, I thought I would just give some knowledge that I have found.
I don't think a single bag will take care of it all, for protection, your going to want to get a sleeve and a bag. Stylish, is going to be purely your opinion, and practicality of use. I'm a fledgling graphic designer/IT college grad, so I'm still into the young sheik look, although I would probably reconsider if going corporate! So here's the lowdown:
Axio - these bags look pretty solid. I was considering one cause I primarily bike everywhere I go. The problem being side protection for your laptop. If you fall sideways, a couple people have reported that side impact (along the zipper) has caused great damage to their laptops. This for me seemed like a big downer, so I ditched on the Axio.
ACMEmade - these bags are really cool, even designated cool in HOW design magazine. There isn't much protection as far as laptop proetection goes, but look really nice. Not much room for anything but the book, so its more of a light travel to the coffee shop kinda bag. I'm considering getting one, but only as an accessory to a main setup.
Booq Bags - They look decent, functional, and in my opinion, simple is nice. They made a new Vyper sleeve, which I plan on getting, only it won't ship till April at the earliest. The sleeve seems SOLID, and they recommend pairing a sleeve with bags as a means to laptop protection, because honestly, I don't know of any single bag solutions that would make anyone feel super secure (contents shift, bags fall, its just not really possible with the various laptop sizes and forms). The sleeves fit certain laptops like a glove, and that will protect it pretty well. Pop it inside another bag of cosmetic liking, and go with that for looks.
CHROME bags - these are courier bags, which I must say, ROCK for riding on a bike. I just got one, and its bomber. The look is a little odd, but ultimatley looks pretty cool, and is a very functional design for a messenger bag. I'm going to pair a Booq Vyper sleeve with this bag for aroung the town biking with my laptop. These aren't laptop bags, just something different to give you options for outside carrying bags.
For you, Sir Sheik... go with a rugged and bomber sleeve like the vyper, and then wrap it with a ACME bag (the wider non SLIM ones) for superstar looks. That seems to be the look and functionality you are looking for. If that isn't to your liking, get a Vyper sleeve, and put it in a CHROME bag, but get a white one. Then, use a sharpie and let your creative side loose. It may sound crazy, but it might be worth it to just be original. Nothing pre-made is gonna top your own hand drawn masterpiece. As long as it means something to you. If anyone asks, say you got it at URBAN OUTFITTERS.
In the end, ROCK OUT....
Jonny Gotham