Thanks for the feedback!
I like to pair my makeup with my clothes, so that's part of the equation for me, but the main thing is the changing seasons, especially how the days get longer/shorter and the light gets brighter/more diffused. The light quality is a big deal and makes or breaks me looking too made up and haggly, especially at my age.
Right now, I'm cutting back on the pastel lipsticks and the bright glosses and going more towards the HC and Semi-Precious lipsticks and low-key gloss, but I'm still using face products with shimmer. When the days get shorter, I'll use fewer MSFs and more matte and satin face powders and move into the vampy lip territory when the days are very noticeably shorter- that's when I'm wearing more black clothes too, so it works better. Actually, Style Seeker has perfect colors for right now for me, so that's getting a lot of use. I also wind up using cooler toned shades in the late fall/winter/early spring because I get paler and the warm undertones in my skin go away some. I don't use bronzer very often in these seasons either. A good example is what nude lipstick I use: Winter= Restrict, Spring = Playing Koi, Summer = Salute! and now Fall = Delectable/Cusp of Dawn.
If I was living somewhere where it was already rainy and cloudy a lot, I'd probably already be busting out deeper colors etc.