I have many lenses in the medium telephoto range. Some are macro lenses and others aren't. For a tightly cropper portrait a 50 is too short. If you are doing an environmental portrait and you will be the same distance from the subject that you would be with an 85 or a 100 then where facial features are concerned you are OK. My favorite portrait lens is probably the 100/2.5 Minolta MC Rokkor. I have three of them. The only time I don't like the 100/2.5 is for a tight portrait of a young child. The lens doesn't focus close enough for that. Using medium telephoto macro lenses for portraits has been discussed many times. It can certainly be done but the rendering of the skin may be too harsh and the out of focus rendition behind the subject can be unattractive. Another favorite portrait lens of mine is the 135/2.8 Vivitar Close Focusing. It gives a slightly different look from an 85 or a 100 but it is still a good look and goves a little more working distance. Other lenses I like for portraits are the 105/2.5 Nikkor (old and new designs), 100/2.8 Canon FD SSC and New FD, 85/1.8 Canon New FD, 85/1.8 Canon FL, 100/3.5 Canon FL, 85/1.8 Konica Hexanon, 85/2 AI Nikkor, 100/2.8 Zuiko. If I don't have to get quite as close, the 135/2.5 Canon FL, 135/2.5 Canon FD SC and the 135/2.8 Nikkor QC/'K' lenses all have very nice out of focus rendition. If I'm feeling strong I might carry a 135/2.3 Vivitar Series 1. This lens focuses to 3 feet. I have one for Konica AR and one for Nikon AI.