Day 1: Dior Fascinante
For the first day of the challenge, I definitely eased myself in by applying a matte red lip that didn't seem too intimidating in the tube. Because it was a flat formula, it was a bit drying. It rubbed off pretty easily, which I noticed when I took my first sip of morning coffee and saw a pale red lip print on my cup (I fear I also ate tons of it during lunch).
However, I felt comfortable in this all day and even got a few compliments on it (though I'm not sure if they were "OMG cute color!" comments or "OMG you're wearing lipstick whaaat?!" comments), which was encouraging and geared me up for day two.
Product: Dior State of Gold Holiday Collection Lipstick in Fascinate ($38)