The outback definitely has a bit of an edge in regards to being upscale, as that's where it fits in within subaru's lineup. The interior etc feels a bit more high end and quieter.
For highway use I'd probably go with the outback. The CVT or 6mt will give better highway mileage, and it has a bit smoother and more planted feel on highway use.
Forester wins out for around town, offroad etc.
Not sure if they've fixed the issue, but outbacks have had problems in the past with a steering "shake" issue.
I'd try to get as thorough a test drive as possible with both, it's really up to personal preference. I personally like the 05-09 outback and 03-08 forester much more than the newer ones. I like the 09+ foresters, but they do feel a bit cheaper than the older models imo.
04xt/4eat, 16g, STI bits and bobs