I guess I see it differently.
It's not about a feminine/softer side. It's that I try to choose clothes that make sense (to me) for the activity. Cotton briefs generally make more sense to me than shiny panties (which I would only see when undressing) because of the weather (it's usually hot!) and the fit (the tools don't fit inside the pretty toolbox). For a dressy occasion, I typically prefer a dress because it's physically more comfortable (I tend to not run as hot as with a suit, and I can breath better) and more interesting to look at (other people are see it, but I get to see it more, too). Putting on female-designated clothes does not make me feel feminine or softer -- they are just clothes. If they are ones I don't like, I'll probably be uncomfortable, and if they are clothes I like, I will probably be more engaging. But then, it's more or less the same way with male-designated clothes.
I want to dress for the occasion, really.