Skirts and dresses can be very comfortable to wear, so yes men should be able to wear skirts and dresses without being classed as gay, transgendered or a drag queen. It is about time that all fashion became unisex, which would end the discrimination that men currently face when choosing to wear something deemed to be 'womenswear'.
I think that guys should be aloud to express themselves and if they want to by wearing a skirt then let them, and you never know it could be there religion or it could be there gender orientation for say, he could be gender fluid, like one day he feels like a man the next he feels like a woman you never really know
In Scotland, men wear kilts and kilts are a type of skirt. Also, men have worn skirts in wars and have worn skirts THROUGHOUT the course of human history so how is 2016 any different? Women are allowed to wear men's clothes so it would only be fair if men were allowed to wear women's clothes! Plus, there are just men who like to cross-dress and there are women who like to cross-dress too. As long as they're not wearing anything inappropriate or doing anything harmful, then let them wear whatever the hell they want to!
The only thing holding men back from wearing skirts and dresses is sexism. Men are so worried about what todays society expects men to dress like that they hold back there desires. What is a skirt or dress but just a piece of fabric. Why not make more masculine skirts and dress in the same fabric. After all a pair of plain black trousers is so boring. Skirts are better for your genitals. I am not gay or a transgender but do feel the comfort of wear a skirt or dress around my own home. I have now desire to be a woman and have a long term female partner. Women wear trousers and suits, should we stop them because they are a men's clothes? Probably not so let men wear a skirt or dress. Beckham, Vin Diesel and Jade Smith to name but a few wore skirts and they are normal heterosexual men. If you want to wear trousers then that is fine, if you want to wear a skirt that is also fine. Still a man under the material. Worried about the skirt blowing up in the wind and showing the genitals, same thing can happen to a women and show parts of her both she does not want to show. Men can wear a pair of light shorts underneath if necessary. Another argument men's hairy legs showing , well then wear a longer skirt. Problem solved. Men wore skirts throughout history without ridicule to worry about. Do what ever makes you happy.
It doesn't even matter if the person who classes him is homophob or not, a guy that is wearing a dress or a skirt will be very likely connected to not being straight.
Even though I personaly disagree with men being classed as gay, it doesn't prevent it from occuring.