Shabbos came around and I was doing just fine without makeup; I felt totally comfortable and confident and actually, it was kind of nice not to have to put on makeup, my face felt so fresh and clean.
However, I was in Crown Heights for Shabbos and that may have had something to do with my comfort level since I cared significantly less what people think of me since it's not my community. The more significant "test" will be this coming Shabbos when I am in Washington Heights where I know A LOT more people. Since I think people perceive me in a certain way, I wonder what they will say when they see me without makeup (eek).
I started to feel yuch and not happy with the way I looked on motzai shabbos. I was going out with my friends, everyone else was wearing makeup and I was having one of those "I don't have anything to wear" crisis. Usually it's less of a deal, but since I wasn't wearing any makeup it only exacerbated my feelings of looking like poop (work with me here). :) I didn't feel less confident, just felt frustrated that I didn't look good and I was like, "why am I doing this anyway???"
And then Sunday night and Monday night I was "allowed" to wear makeup because I had a wedding and a date, respectively. I almost didn't wear makeup because I thought it would break up the process of my no-makeup journey and that it was hypocritical, but in fact it had the opposite effect! I felt great wearing my makeup and looking a little more glamorous, but when I woke up this morning, makeup-less (a little like Cinderella after the clock strikes 12), I looked in the mirror and thought, "Oh hey, you look pretty," and felt totally comfortable in my skin! :-)
This shocked me because I thought it would be really hard to go back to not wearing makeup again, but if anything it helped me feel more at ease. It doesn't have to be all or nothing and when social etiquette calls for a lil' glamour, it's important to step-up. But I don't need it to feel comfortable going out and THAT's important too.