Gents, I have a heavy, well actually very heavy, briefcase/messenger bag very similar to the Saddleback Leather bags. Recently, I have become disgruntled with it although it is sturdy and very handsome it just doesn't serve my purposes as well as I think "something" could. I have my pack options covered for hunting, hiking and camping(same pack) but that is an entirely different can of worms.

Although I am finished with school, and what I believed would be the end of toting gobs of books etc around, I have found that now I might actually carry more. Now it is files, a camera, a portfolio, pens, various literature and a laptop/charger. There are also the other things I carry anyway; phone, keys, multi-tool, flashlight, knives and the like.

I had tried a Filson bag, the "medium field", I believe it was called but my computer wouldn't fit in it.

So, what do you guys use?

Jumbo Maxpedition Versipack in OD. I got it on eBay for $50 shipped! I'd like a Janus attachment for the strap, but they're like $30. Too much when I got the bag for $50. For anything bigger, I use a messenger bag or a North Face backpack.

That Versipack is very cool, I had one and it was really nice. Wasn't big enough for my PC though.

That NRA bag looks really cool! I wonder if it is a bit conspicuous for the office?

That NRA bag looks remarkably similar to Oakley's bag.... and Oakley's bag has all the looks of a tactical heavy duty bag but it's kind of... imitation? I mean it's made to look sturdy but a lot of it's design doesn't serve much function.

I recently bought one of TADgears newest offerings but it just wasn't large enough for all the day to day back and forth to work stuff. Dispatch Bag It's really sturdy if you're looking for something like a brief case but it just doesn't have the volume to work like a small back pack. AND all of the molle webbing on it is pointless:
- back side - not going to attach molle pouches there
- inside pockets - not enough room to attach pouches there

So I went back to the same bag I've been using since 2000 made by Spire USA. They no longer have the exact same model I have (about 16 x 6 x 12), but it's lasted. Well thought out, plenty of room for everything I carry around plus lunch breakfast and more. Here are their latest offerings: Spire USA
What I'd really love to see is a marriage of the two above bags. I can't stand pockets/pouches and other details that don't make sense or don't efficiently use space. (google stomp II)
Maxpedition has some great designs and really innovative ideas, two complaints I have are (1) their cordura/nylon tends to be really STIFF (2) their compartments/pouches tend to be really small (and coupled with (1) tends to be a pain in the neck to get in and out of) Gonna have to add a third but I'll call it an observation - they actually "overbuild" - so many layers of webbing/velcro/nylon for multiple adjustments/attach points has some of their items (like a radio carrier for instance) adding an insane amount of bulk to the item you're carrying.
Will try to post pics of all the above later, if not by this weekend.

edit: just remembered this company Timbuk2 they make really rugged bags, a little pricey when compared to the Spire

These might draw less attention at the office.

http://www.wengerna.com/computer-cases

I carry this one to Company meetings (insurance) all the time and haven't had any strange looks or comments. This one however won't carry your laptop.

http://www.wengerna.com/content2920

That TADgear bag looks really cool, like you said though it wasn't big enough for you. The Spire bag reminds me alot of the Timbuk2 bags. My experiance with bags like that is if they tip over your stuff can fall out. Tonight I am going to see what stuff I can get out of the bag and how much space I would have to have.

I like this bag. sure it looks a bit tactical, but no more than carrying my maxpedition collosus into the office. I found what appears to be the same bag here http://www.sportsgearsuperstore.com/product/9968ACU in different colors.

and a bit cheaper.

I like the swiss army bags nice

There are alot of bags to siv through at LA Police Gear's website. I wonder how much difference there is between one and the next.

Tactical Gear has taken off the past 5 or 6 years. There are a lot of quality products out there and a lot of knock offs. Criticals are Materials and Design - well crafted gear that just doesn't make sense, well designed gear with chincy materials, and poorly crafted gear with chincy materials. Here's a pic of two types of webbing:

the webbing on the left has too high of a plastic content and a really loose weave as opposed to the one on the right with a tight weave and probably a 30 - 70 cotton to polyester content. The high poly doesn't last as long and is basically more prone to accepting abuse. (5.11 gun bag shoulder strap left, Maxpedition right) Grades of webbing span the gambit from really thin to really heavy duty but if it looks too "shiny", burns really easy, and looks really "loose" it's not gonna last.

As for the OP and EDC Bag/Briefcase here are some pics of the TAD next to the Spire (and you posted being concerned about falling over and spilling out - the TAD was more prone to falling over, seems I was always picking it up, have never had a problem with the Spire unless it was a case of it sitting in the passenger seat and having to jam the brakes)

Basic stuff in the Spire - dayrunner, organizer, stenopad:

same items in the TAD: (the TAD seems to lose space because it has foam padding sewn into it all the way around - Spire only has it on the back (it came with a separate padded laptop sleeve)

It may not show it in the images, but with the Spire I could probably fit about a dozen grapefuit into the bag, with the TAD I'd have to cut them all in half - hope that gives perspective. I'm using the TAD as a laptop bag, it's got plenty or room for that and accessories.

Maxpedtion: here is a small pouch next to an Eagle Industries pouch:

Maxpedition makes some well built stuff but you're gonna pay for that versatility with bulk and it can add up.