Back in April of 2021 I posted "Can A Man Wear Women’s Clothing? Daaah!" The article I quoted was from a Pinterest link and it had many good suggestions. Go back and see the article here: Real Men Style.
What I found most interesting were the comments the Pinterest link generated. I especially like the last one.
Chris: I dressed up as a girl for a costume party and it opened my eyes to things. I'd wear a skirt or dress all the time if I could due to comfort. I now have pantyhose and tights as part of my wardrobe in winter. I wear them under pants and jeans for added warmth and they just feel good to me. I will sometimes wear them in warmer weather with shorts to keep bugs from boring my legs. I think you should be able to openly wear some of these things without being seen as girly.
Samantha: Absolutely we men can wear (female) clothing I do agree that some of female clothing is to femme for men but a lot can be used as unisex clothing for both sexes I’m example jean skirts solid color dresses tights heels stockings even makeup we men have a soft side also.
Stephen: I usually wear a denim skirt with a polo shirt on weekends when not working. I shave my legs, paint my toenails followed with a pair of pantyhose and high heels or sandals
LisaP on my site: He has made some good observations, and maybe it will help push the envelope. But, he also repeats some negative comments -- referencing the Hebrew Bible, for example, to say "don't worry guys, you are violating any social or religious laws by following my advice.
Tristan: if it fits, you can wear it