Busy travel is an increasing way of life for me. As such, I decided to upgrade my luggage to accommodate this new reality. In part, this was brought on by my prior bags wearing out (I had one of the original REI Big Byte computer backpacks and a ultralight 2-suiter shoulder bag from Skyways).
My first question was what to choose for laptop bag. I'd previously used a backpack, and was general fond of having it on my back, but I'd also become a bit weary of lugging around a shoulder bag for clothes. In retrospect (and, perhaps, forethought), I probably should have stuck with a computer backpack since I think the contents are generally heavier than my clothing. At any rate, for ease of passage through security checkpoints, I opted for the Tom Bihn Checkpoint Flyer.
The Checkpoint Flyer has a padded laptop compartment that can flip out to be run through the TSA scanners w/o removing the laptop. You just have to unclip in two places and zip-through you go. To supplement the Checkpoint Flyer, I also bought a Horizontal Freudian Slip to provide a nice set of organizational slots for pens, business cards, files, and - in my case - a 13" MacBook Air (which fits perfectly in one of the file folder slots).
The Horizontal Freudian Slip fits neatly inside the main compartment of the Checkpoint Flyer, with room to spare. I find it helps make better utility of the space in the middle section. Though I haven't tried it, you could probably also fit an Eagle Creek Pack-It Folder 15 in there instead of the Freudian Slip, such as for less business-oriented travel. The Checkpoint Flyer also has 2 large pockets in this main section, which nicely accommodate a variety of things. I keep a first aid kit, snacks, and a quart-size bag of miscellaneous pill containers on one side (advil, tylenol, allegra, toothpicks), and I keep a mouse and my liquids ziploc bag on the other side. The Horizontal Freudian Slip leaves enough room for both a Kindle and a typical mass-market paperback book. The back of the bag has 2 slots, in which I can carry a file folder (generally where I stash my travel docs) and a small pocket that fits a 0.5L Nalgene bottle.
I also purchased one of the Tim Bihn Absolute shoulder straps to go with the bag. This is essential since I don't plan to carry it in my hand very often. The strip is very comfortable and sticks to my shoulder at all times. It seems to employ a rubber/neoprene-type fabric that increases comfort and stickiness.
I've been pleasantly surprised just how much I can put into this bag. The two outside pockets are ideal for most power supplies and cables, as well as a variety of other electronics. Under the flap are 2 wide pockets that also fit a variety of items. I typically cary a mifi device, presentation remote, battery recharging pack, numerous cables, VGA and DVI adapters, and a variety of cables.
For carrying clothing, I've opted for a backpack that is designed to fit into any overhead bin, regardless of aircraft size and country (apparently European carryon rules can vary widely). The Red Oxx Sky Train is a very versatile bag, provide 2 handles (one on top, one of the side), a shoulder strap, and packable backpack straps. This is an extremely durable bag that is built with heavy nylon and some of the strongest zippers I've encountered. On the down-side, this comes at the cost of weight and - in the case of the shoulder straps - comfortable backpack straps.
Overall, this bag has remarkable capacity. In the main compartment there is room for a fully-loaded Eagle Creek Pack-It Folder 18, and then another layer of packing containers (I use a half-size cube and then either my hygiene bag, a pair shoes, and/or a variety of other things). The middle compartment is similarly roomy, though at about half the depth. It easily fits the laptop compartment from my Checkpoint Flyer, which is handy when I'm traveling light and want to reduce some of the load in my shoulder bag.
One of the weak points that I didn't anticipate properly is carrying a suit or sport jacket. You can certainly fit it into the bag without a problem, but ensuring that it avoids wrinkling is a puzzle I've yet to work out. In particular, keeping the jacket wrinkle-free doesn't seem to work. It's possible I could put it in the Pack-It Folder, but I'm not sure it's ideal. I have read that packing in plastic covers will help reduce wrinkling, so I may give it a go next time to see how well it works. In the meantime, it's not necessarily unreasonable to wear the jacket, or carry it separately (most airlines will allow you to carry a separate thin hanging bag in addition to your 2 carry-ons if it is thin and doesn't take-up much room).