I use more oil in the winter - I oil both morning and night.  I usually wash my hair in the early evening so that it is mostly dry by the time I go to bed.  I use just a tiny bit of oil on the ends in the morning.  This helps keep the static under control.

I've recently started oiling morning and night.  I've started using camellia oil.  One or two drops and my hair is not greasy looking like from other oils.  I just oil the ends, from the ears down.  I also apply a little oil when my hair is wet.  I use product regularly-a leave in, gel, and a moisture lock spray.  I apply the oil by scrunching it in up to my ears after the gel and before the spray.  My ends have never looked so good.

I only do a "heavy" oiling before I'm going to wash, which will be late afternoons now that it is getting cooler.  I use sesame oil for that, and massage my scalp as well as coat the strands.

I will still use the oil daily.