I used to not wear a lot of makeup, except for special occasions. I always enjoyed putting it on, so I decided (partly because glamourpuss) to wear it more often. I see it like MacMadame, a hobby thing. I do it for fun, for me. I wear different types of colors, styles, for fun. And I like the way I look with a little mascara and highlighter.
I hate that attitude. It is everywhere, though. I was once told by two women in a graduate class, where I was a "visiting student", that they found it shocking that I could discuss the topic intelligently because I wore make-up and nice clothes.
I have been in discussions with women in software about dressing for interviews, and the conclusion is: Don't wear a lot, or even any, makeup for interviews. Don't dress up too much. In fact, if you have a game or software convention t-shirt, wear that!
whenever I went to a social event, wearing makeup and told them I work for Microsoft, people would ask if I was a Program Manager. No, I am a developer. Oh, you don't look like one...
When not wearing makeup I the conversation would go a little different. This might have changed a little for the better in the past 5 years, but it is so annoying.
So I am a developer. With makeup. Or without. And I wear skirts with flowers. Sometimes jeans. (though I have no style

).
Speaking of playing around with stuff, today I put some eyeliner in my lower lashline. I don't think I like it, makes my eyes look small and squinty. Isn't it supposed to make them look bigger? When ever I see someone with eye shadow or liner in the lower lashline or just below the eye I want to try, and it always looks odd on me. Maybe because my lower lashes are quite long (I never mascara those)?