I think we need to define "dressing" before we can answer the question accurately. If it's just panties, I dress every day. Same for women's jeans. All my jeans are from the women's section but I wear them as a male. I wouldn't call it "dressing" without a wig and at least lipstick and beard cover.
So my answer is, I dress with women's clothes and shoes, boobs, hips and hair nearly every day unless I'm away or doing something outside of the house. Not all day perhaps but half a day.
