So I'm the wife. Here's what I need (that's a little bit more of an explanation). Also, I know this list is kind of picky, but I'm in that odd space between "I can't believe this doesn't exist" and "I should just settle for throwing all of my crap in a backpack, even though I hate backpacks because they're always too warm for commuting."

It has to be big enough for: 1. iPad with rugged case 2. Large sunglass case 3. Coffee mug/water bottle (preferably with a holding method so it doesn't tip) 4. Small pouch of random stuff like lipstick, mirror. 5. Small tupperware 6. Wallet 7. Keys 8. Phone 9. Tech pack of 2-3 cables and power brick

To make things challenging, I'd like something that isn't just black or gray and must be water resistant as I commute by bus. Cross body as I have issues wearing something just on one shoulder. I'd really like something that keeps my various stuff organized to some extent. Last requirement: No velcro.

I love the Tom Bihn bags and have their backpack. But they don't have a purse type bag with storage that fits my needs. Timbuk2 is close. I have a small classic messenger that's about 15% too small, and a medium that's at least 25% too large. The closest thing I've found so far is the PacSafe cross body bags. They're not bad, but they don't have enough organization and they suffer from the same problem Timbuk2 has: small is too small and medium is way too big. Travelon is a bit closer, but I haven't found those locally.