I started about 20 years ago when I was in my early 40's.
The key for me was in October 2016 when I went to Sephora for a makeover. I had a great MUA, Julie, and I took notes and bought much of the makeup she used. That gave me confidence and the tools and process and that has made all the difference in the world. I recommend scheduling a makeover for yourself at Sephora or another place.
I have also found that less is more. I try to get the foundation right; cover my beard, but not so much I look like a drag queen. These days, I usually don't do my eyes other than mascara. I figure if someone is close enough to see my eyes (I wear glasses), they likely know already I'm not a GG. It also makes it easier to clean up afterwards, and saves me time.
