Yes. The easy answer to this is yes. As long as you are not violating any laws (such as nudity laws), you can wear whatever you want in public. If you want to walk around in a clown costume every day, then that is your choice.
While it might be legal, most people are not discussing the legality of a straight man wearing women’s clothing in public. When this question is asked, they generally want to know if it is “weird” or socially acceptable. Personally, I think that you should be able to wear whatever you want without anyone thinking about you differently. I also am personally confused as to why you exchanged clothes with large pockets for the tiny, useless pockets that come with women’s clothing. If you want to exchange comfortable, functional clothes for the non-functional, fashionable women’s attire you see in magazines, have at it.
The real problem that guys run into is how other people will react. There is a real chance that some people will not treat you the same when you wear women’s clothing. This is not necessarily a bad thing though. Back when I was more of a hippie and not aware of how cultural appropriation worked, I had dreadlocks. Immediately, I noticed that other people avoided me when I had dreadlocks. I quickly realized that this was actually a good thing. People who judge your ‘locks were not people that I wanted to be around, so my new hairstyle basically filtered out the world. If you are wearing women’s clothing, you will probably experience the same effect. Some people might stop talking to you, but those are probably not people you would really want to be friends with anyway. If donning female attire makes you happy, forget about those people.
There is another reason why this might not really be a problem. In the last few decades, men’s and women’s clothing has grown increasingly similar. Remember the emo styles that were popular a few years ago? If you missed out, one of the emo options was for guys to wear skinny jeans or women’s jeans. This was an actual, official style. If an entire style for guys could be based on women’s clothing, why not just wear ladies clothes?
In many cases, no one will even notice that you are wearing women’s clothes. If you are wearing a sultry dress, people might notice. If you are just wearing a sweatshirt and jeans, most people won’t realize that you aren’t wearing men’s clothing.
Women still have a long way to go to fight for equal rights and equal pay. As recent scandals in Hollywood and politics show, even obvious sexism like sexual harassment or assault are still extremely common. When it comes to clothing, Western nations need to give men equal clothing rights. Women can already wear traditional men’s clothing—button-up shirts, jeans, slacks—without anyone noticing. Wearing pants has become so popular that it is the default clothing option for women.
While women get to wear traditional male attire, men have not been given the same option. How many times have you thought that a skirt would feel nice on a hot day? If you are like most guys, you have probably wondered how much cooler and breezier a skirt would be. As a skirt wearer, I can tell you that it is an excellent option when it is hot out. Why can’t men access women’s fashions in the way that women can use men’s fashions?
Be a rebel and wear a skirt. Show the world that they are being hypocrites in only approving one gender to wear certain clothes. More importantly, get people to start thinking about gender roles and stereotypes. There is absolutely nothing that says that skirts and high heels are only for women. We have two legs like guys do, so why can’t both genders wear what they want? In the case of high heels, high heels were actually designed for men at the French court. It was originally a male style. Once women copied it, the men stopped being as interested.
The entire way we dress is based on how we are raised and our culture. You can easily see this by looking at different cultures. In some cultures, women and men wear long robes or different kinds of veils. In many European nations, nude beaches are a popular option in the summer. The entire way we dress is determined by our culture, but you don’t have to listen to these restrictions forever.
Ultimately, straight men can do whatever they want. If you feel more attractive with a kilt or skirt billowing around your knees, have at it. It is not your problem if other people judge or disapprove. They have issues—you’re just wearing a skirt. If it makes you happy, go for it.