For me, as a general rule, I usually use plastic finger picks when I want to finger pick a song. Personally, I have never had very good success keeping my finger nails conditioned to the point where they are a good finger picking tool. But that is just me personally! There are those who do go through a lot of trouble to use only their nails. Why is that? They have their reasons! I will discuss this subject more in the next section. However even for me there are times when I may prefer to use only bear fingers and nails. Why? For some songs, volume may not be an issue. In that case bare fingers and nails may be preferred over using picks because of wanting to get that particular unique sound you can get only with bare fingers and nails. Especially is this true on a classical or concert type guitar (with nylon strings).
There are certain genre of finger style guitar that always uses only their bare fingers and finger nails. Spanish guitar, Flamingo, and Classical guitar are of that school of training. There are some awesome musicians out there that play these styles and they can blow you away with their aggressiveness as they attack certain parts of their solo pieces. In order to do this their nails must remain strong to handle all that pressure. Serious musicians of this kind will all tell you that they must spend considerable time taking care of their nails. Frankly, with some of what they do, plastic finger picks would not help at all! Finger picks would only get in the way.
However, there are some who play contemporary music on contemporary guitars (with steel strings) and still they say they prefer finger picking only with bare fingers and nails. Why is this? For many of these I believe they say this ONLY because they don’t REALLY KNOW HOW to use finger picks. Since they have never learned to use them properly I believe this is why they say they prefer not to use them. For others though, they may prefer the bare fingers and nails for other reasons. Gordon Lightfoot is a good example of this. He is hands down one of my most favorite artists. Yet I have never seen him using finger picks! He appears to use only bare fingers and conditioned nails, sometimes with a thumb pick. I don’t know if he has ever tried using finger picks or not. So I can’t say anything about that. But I have heard those who know him well say that when it comes to his music he is a perfectionist. Now that only stands to reason! Some of his songs are absolute masterpieces. So why would he NOT use finger picks? Clearly there are some advantages of using only bare finger. So next I want to talk about the pros and cons of using finger picks as compared to using finger nails. Considering this may help you in your approach too!