I too am an "eyeshadow/eye makeup" geek. I have WAY too many shadows, just love the colors! When I doodle, I design eye makeup looks. And I'll start with the intention of doing something simple--a swipe of cream, liner, and mascara--but it seldom ends there. I've been working from home and often don't wear makeup during the week; seems pointless to put it on to go to the grocery store, make and eat dinner at home, and watch TV. At first, I would avoid mirrors when makeupless, felt odd; I'm better with it now. But it's not a bad idea to experiment with lighter looks for casual/outdoor events. For example, I inline skate outside, and really heavy eye makeup can be problematic on the trail (wind in your eyes).
I suspect you are fair with OLIVE tones, very difficult to get a good match. Few foundations offer proper olive tones, virtually none in the lightest shades. Olive is very confusing, it's primarily a green undertone, and no one knows what to do with it. When you apply a foundation over the face that doesn't match well, one tends to look sickly and/or unnatural. NYX makes a series of foundation mixers to correct tones, including an olive one (it's only $10). If you decide to try this, you'd need to start with a neutral tone foundation too light for you (since the mixer will darken it). The technique of applying stripes and checking in natural light is the correct one. You may already have the right "base" to start with. Re: color types, yeah, it can be challenging. My fave site is https://12blueprints.com/; she doesn't limit types by eye color or hair color or whatever. I recently realized that under her system I'm a Bright Winter, which is why the usual advice to older women to soften their makeup (pale pink, brown, boring!) works for me only if I'm auditioning for The Walking Dead. Over the years I'd come to describe my skin tone as "fair neutral leaning cool," which doesn't mean I want/need a foundation that is PINK, ick! But obvious yellow is just as bad. In the 12 Blueprints, the "seasons" are a continuum; to oversimplify, the "neighbor" types share a bit... For example, Bright Winter is "next door" to Spring, and it takes the very cool, very blue colors of True Winter and adds "a drop of sunshine" (yellow), as well as punching up the intensity. I always wondered why I could wear insanely bright colors and look NORMAL. In fact, I look SICK in pastels (muted/greyed; icy, now those can work). Re: skin tone, the overlap means that the skin of a Bright Winter is still primarily cool, but has elements of warmth, to be more "neutral" with a slight coolness. I can't wear orange, but peach is OK (not my best, but OK)... though the right coral lipstick (toward pink not orange) is great. Hope this helps, good luck!
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