I just go with my mood. I don't have a ton of makeup, so I usually don't have much trouble deciding what to wear. ;-) And I keep my shadows, blushes, & lipsticks/glosses categorized by color family. Easiest to do with shadows because a majority of them are in palettes. If I'm in the mood for a golden look or whatever, I just go through what I have to get that look & pick whatever specific products strike me at the time. I tend to remember my favorites looks too & sometimes just go with those if I'm running behind schedule.

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Dark brown hair, brown eyes, NC25 skin, combo/dry