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When I transitioned some sixteen and a half years ago, at first I did the "makeup and dresses every day" thing, but for a mercifully brief time. I stopped worrying about makeup when I discovered I was getting "sirred" with it on, and "ma'am-ed" with it off, so I toned down my look considerably. Besides, it was a pain to put makeup on every time I went out. Though I still do the "dresses all the time" (or most of the time) thing during the summer, if only for the sake of comfort.