I've been looking through this forum for a few weeks, trying to find someone else who wants something similar as me. I've looked through all of the recent suggestions for a laptop bag, backpack, and most carry-ons, and just haven't seen a bag that jumps out at me.

So here's what I'm looking for. A bag that could hold the following items:
* my work laptop (a Thinkpad X220, I think it is 11")
* my personal MacBook Air 11"
* chargers for the above, and a Kensington 3-plug + 2 USB power adapter (has been a lifesaver when outlets are scarce)
* cables for iPhone, Blackberry, and occasionally the devices themselves
* headphones (in a hard case), earbuds, and a Kindle
* a small amount of clothing (can be rolled), such as 1-2 t-shirts, underwear, socks, perhaps 1 long-sleeved shirt
* Garmin Forerunner, as well as the charger, and USB
* toiletries
* snacks
* any work files, trip files, bus cards, etc

I currently have a TravelPro 22" roller bag (2011 model), which is fantastic, but it rolls. And if I use that, I'll pack more stuff and fill it. It can be a bit of a PITA with stairs, and getting on/off subways or other transit (the Boston T's green line has stairs as do many of the stations).

I also have a variety of backpacks and laptop bags. Last year I bought a SwissGear backpack from Staples on sale for about $80, and 2 zippers broke during my very first trip. I still use it, as the zippers that broke (thankfully) are on tracks where there's also another zipper, the broken ones are just stuck on one side. Oddly, a High Sierra computer backpack I got on sale at Dillards about 10 years ago for $50 has held up surprisingly well, I'm just looking for something that looks nicer. I have a small messenger bag that can hold my MacBook Air, but barely anything else (and it won't even hold my work laptop).


Ideally this new bag will see the following uses:
* solo bag for a quick overnight/weekend trip, or a mileage run (usually do 1-2 Europe runs a year, for 1-2 nights)
* additional bag that I'd carry onboard for longer trips, with the bulk of my clothing being checked
* perhaps replace the 7 year old laptop bag I drag to the office (but this isn't a high priority)
* travel with me for biz trips, perhaps solo or in addition to another bag, and would go with me into meetings and such


I'm open to a backpack, messenger-style bag, or other ideas. Either way, I want something that is sturdy, and won't kill my shoulders. If a messenger-style, it needs to have a good strap with awesome padding.

Budget--I'm kind of open. I don't want to say it is unlimited, but I've certainly found that money usually buys better quality. If I get a good recommendation, I wouldn't hesitate to pay $300 or so.
I've looked at some bags at Nordstrom. Some have the look I'm wanting, but I'm not sure they'd have the functions I want.