I've always thought it's better to spend more on something once than to buy cheap and replace time and again. Because of this, I've owned exactly two bags in the last nine years: a Wenger Soho backpack and now a custom, $184 Timbuk2 Laptop Messenger. Last spring I decided it was time to retire the trusty Wenger that got me through college and my first three E3s for something a little more modern.
Timbuk2 Custom Laptop Messenger IRL
What pushed me toward Timbuk2 was the number of pockets and compartments inside -- its bags aren't just buckets with a strap. Moreover, in addition to getting a bag that looked exactly how I wanted, by going custom I was also giving a job to one of Timbuk2's San Francisco bag-makers, and I'm all about supporting domestic manufacturing whenever possible.
I wasn't sure a medium would be big enough after scoping its dimensions online, but when my bag arrived just over a week later, I was happily proven wrong. My current haul is a five-subject notebook, a 2-inch three-ring binder, hardcover versions of Jurassic Park and Blood Meridian, a Moleskine, my 13-inch MacBook Air and PS Vita. That's not the half of it, though, because I'm also schlepping all kinds of wall adapters and charging cables, a smattering of writing instruments, business cards, two voice recorders, a few paperback novels, two notepads and a travel mug. Heavy? A bit. Disorganized? No way.
I'm horribly scatterbrained, but I have absolutely zero problems finding anything at a moment's notice in this bag. The pouch inside a pocket that resides inside yet another compartment isn't just a feature that'd make Xzibit smile; it's something I use constantly. The pack has a safe and secure place for everything I'd want to carry with me and more compartments than I'll probably ever take advantage of. For me, that's priceless.