I use to use a LV Odessa computer bag daily in taiga grizzli brown leather. I paid about $1700, but LV likes to increase prices and I think it's up to $2200 now. They recently updated the design and fixed some of the issues. I fly twice a week and got paranoid that someone would steal the bag (and contents) from the overhead bin because I got so many comments and complements about it. I think the color is different than what most business travelers use so it stands out. It looks sophisticated yet a bit more casual, especially in the brown.
The Odessa was replaced as my daily use bag by a Tumi Formula T Coupe Slim in black (~$450, but discontinued), which just barely fits the 13" MBP, small notebook, slim Sony P&S camera, iPhone, wallet. There is larger version which would fit the 15" MBP and more natural leather color as well. You can get one on eBay occasionally since the entire Formula T line was discontinued. Mine looks almost new after over a year of use and 90+ flights.
When I don't carry the computer, on more casual occasions, I use a LV Andrei bag to carry the camera / camcorder, maps, small umbrella, etc. I can't stand any of the monogram patterns, but some people love them. The leather versions are more expensive but get less attention, which is what I like. A smaller Apple tablet device would fit nicely...
While very expensive for what they are, I find that the resale value for LV is much better than for used Tumi bags. I've been able to sell my used LV for close to what I paid even after a few years of use.
I've also been looking at the
Porsche Design White collection, but it's not exactly casual looking.