I'd go with the 85mm if full frame, the 85mm if DX. You read that right. While I LOVE my 50mm 1.4, it's definitely a focal length that is kind of weird and takes some getting used to. I find on DX I'm either much closer than needed or much too far away about 70% of the time. I'd much rather have the separation between the background and the extra distance. The 50 is an everyday lens on FX, but is the 85 is where reach starts happening. And reach is good when it comes to portraits. Since we don't yet know what camera you're using, that's my 2c.