The bag is very much a looker. My paper's executive editor saw it perched on the edge of my desk and raved over how elegant it looked. It's sewn together well -- actually, a little too well. The pen/pencil pockets will carry standard sizes, but my fountain pen or Ph.D pencils wouldn't fit. The other pockets were a bit small for my taste, and I didn't want to try fitting my iPhone in there. I was also disappointed in the padding of the laptop compartment; I felt it could be a bit thicker. However, there is plenty of space inside the bag, and it easily swallowed up a good bit of what I carry on a day-to-day basis without bulking up. It's made well and should last someone a good bit of their professional career.
However, the bag grew very heavy quickly. I loaded it up with my 11-inch MacBook Air, power adapter, Kindle and a few other odds and ends. The bag really shouldn't be quite as heavy as it was, and I wish it had longer straps to compensate for it. Because of the shorter straps, the bulk of the load gets placed on your shoulder when you wear the bag over one shoulder. I'd love to see straps akin other bags where you can wear it across your chest and have the weight supported on your hip. The bag is designed to carry up to a 15-inch MacBook Pro, which is far heftier than the Air.
The other drawback to me is price. Tom Bihn's range of backpacks and messengers range from $55 for its new Breve that's just for the iPad and its accessories, up to $220 for the Checkpoint Flyer, which Steve Sande reviewed a couple years ago. Waterfield Designs also has a range of stylish work bags that range from $150-$300. The Apple Store sells a Cole Haan messenger for $399.95, but that bag is definitely not as chic as the Plaid Doctrine bags.
If you're interested in a stylish bag that's also good for the planet, this is a good choice -- as long as you're aware of the caveats. Plaid Doctrine has excellent customer service, which is always a huge plus. Its $69 iPad sleeve is definitely worth considering if you're looking for an eco-friendly iPad case. The fabric is the same as the laptop bags and has room for the iPad charger, headphones and an iPhone.