If you have a wife or a SO that you live with then that may dictate when you dress. I’m divorced and empty nester so I can dress all the time and pretty much do. I sleep in just panties even though I would like to sleep in lingerie but I toss a lot and get wrapped up to easily. I wake up and will slip on either short shorts or tennis skirt or one of those flouncy gym shorts that look like a short skirt. I also like to wear dolphin shorts too matched with either a tank or some cotton t-shirt. If I go out then it’s either denim skirt, dress or short shorts with some type of top like a polo or tank. My go to shoes in hot weather like it is now are sandals and yes my toes are painted, right now with a French tip. I also love to wear block heel sandals too. Even if I’m in guy mode everything I have on are women’s I just don’t have on a wig or forms.
Do I wish I had a SO I could share my love of women’s clothing…sometimes but not enough to want to get into any relationship. I get to be the master of my own remote control and the Queen of my own panties so I’m just fine with where I am in life.