I have a good sense of humor when it comes to crossdressing so am always curious how I might look and feel in a particular item.
For me it was a pink nylon babydoll nightie from the late 60s with several layers puffy material. It even had silky granny panties with ruffles on the butt. LOL It felt amazing and so girly but was so frilly that I thought it was more comical than real. There is no possible way I could sleep in it !
I still have a square Dance Dress with petticoats on my bucket list but can't bring myself to buy one just for a quick thrill !