I'm a fan of saddlebacks, but they're a little much in some contexts. I got a custom one without the rings and darkened it with a brown polish over a few weeks, looks beautiful. it's heavy, which reflects it's quality. custom was about $750 but you can get the regular ones for $400 I believe. it's not super practical though.
more practical is something from filson, which are classics for a reason. but this is a little bit more casual and probably works best in a business casual context. i wouldn't necessarily bring it to a board meeting unless my title was Chairman (though tbf I feel that way about the standard saddlebacks as well, though mine works well in any context).
gurkha is obviously a major step up, but you get what you pay for there. if you're looking for a bag you can use for the rest of your life and that will look sleek and polished in most contexts I'd drop the coin.
i also really like this one and will likely pull the trigger on one in the near future.
http://shop.nordstrom.com/s/rodd-gunn-l ... olor=COCOANAB should weigh in here as well, though he may just give you advice on what bag works best with his square toed rockfords and banana republic slacks.