I think mapping out how I plan the way I'm going to look at the start of my day is an important step in designing a kind of app that may do this thinking for someone. I've done this routine on auto for so many years that I can makes these decisions in really no time at all. I'm going to dig up what I'm thinking and feeling as I pickup my brushes.
1. The first thing I think of is how much time do I have or want to spend. Some days I don't have a lot of time and some days it feels a little like a chore that I just want to get over and done with. I have a few different looks that I'll do if I have around 10, 15, or 20+ minutes.
2. Another thing I consider, and it might be weird, is the season. Yes, I do my makeup differently from season to season. In warmer months, I use less products on my face and ones that are lighter taking sweat, heat, and comfort into consideration. I also like to use more natural looking colors in the summer as they last longer throughout the day. In colder months, I wear heavier foundation and darker colors. In colder months there's really no need to worry about anything melting away. Kind of like "fall colors" with clothes I do the same with my face.
3. Is there an occasion? I won't wear green eyeshadow or purple lipstick to work and I won't have an absence of anything if I'm going out with friends or on a date. There are lots of things to consider!
4. If I have about 10 minutes, I'll skip eyeshadow altogether. To me, you don't need eyeshadow to have a complete look. This can be compensated (if I feel like it) with a more boldly colored lipstick since it takes the same amount of time to do any color. I'll usually skip strip lashes if I'm in a time pinch too, which I usually do wear. Iffy finishing touch things are blush and highlighter. In this time frame I'll do kind of the "bare minimum", which may be like a lot to some people because I've gotten pretty fast: foundation, concealer, light cheekbone contour, eyeliner (always graphic and winged!), mascara top and bottom, eyebrow fill, setting powder, lipstick, and highlighter (usually).
If I have about 15 minutes, I'll do simple eyeshadow like a gold or pink lid and I usually add a dark brown in my crease and lower lash line. I'll definitely wear extra eyelashes on these days. With a mildly bold eye, I will most likely wear a natural looking lip color. I will also lightly contour my whole face, sweeping a brownish color over all the more shadowy areas of the face like under the cheekbones, jawline, and sides of the forehead. Highlights are added to the tops of cheekbones, tip and bridge of the nose, inner corners of the eyes, and just under the eyebrows.
If I have 20+ minutes, let the creativity begin! This is when I pull out my more elaborately colored eyeshadow palette and experiment with more unconventional colors like green, blue, silver, red, etc.. I try to experiment with different blending techniques and shapes too. When I do this, it is always a natural lip color. I don't like to have both bold eyes and lips, it looks overdone to me, I like either the eyes or lips to make a statement, never both.
I don't really think it takes a lot of different products to make this happen. My makeup collection is actually pretty small compared to most. I can fit everything in a fairly small makeup bag with 2 larger eyeshadow palettes that can't fit (and two collector's items from an Andy Warhol collection I rarely use). In the bag I have 6 brushes, 1 foundation, 1 concealer, 1 face powder, 1 eyebrow tint, 1 mascara, 2 eyeliners, 3 lipsticks, 2 lash sets with a glue, 1 blush, and 1 highlighter.
I have also been learning how to use the new program Adobe XD and I think this could be a good program for me to use as it is an interactive app/interface prototyping program.
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