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How To Get The Courage To Wear Women's Clothing In Public

Updated on June 6, 2010

This is a doozie of a leap for many men to make. It is one thing to accept yourself and have fun wearing women's clothing in the privacy of your own home, but to go out of it and expose yourself to the eyes and judgment of the world, now that is quite another thing.

I've broken this article down into sections for ease of reading. Let's start with the basic concept of wearing clothing at all, regardless of its supposed gender orientation.

Why We Wear Clothes

First of all, I would like to say that it is not actually necessary for you to go out in public wearing women's clothing at all. What we wear in public is sometimes a representation of who we are, but more often it is a representation of how we want other people to see us.

People don't spend thousands of dollars on clothing so that they feel good, they spend the money because people react differently to well dressed people. If I wander into a BMW dealership in scruffy jeans and a t-shirt with my hair kind of frizzy, I'd probably be asked to leave, or I'd at least receive far more scrutiny and less welcoming goodness than if I walked in a designer dress.

People are shallow creatures who judge on appearance. We shouldn't, but we do, therefore what most of us wear in public is either a plea to be liked and respected, or a request to be feared (think skinheads and people waving gang colors), or an appeal to attraction as in the case of ladies wearing short skirts and tube tops, etc.

If we come at the issue from this perspective, we just need to ask ourselves what message it sends when a man wears women's clothing in public. Of course, it very much depends on what he's wearing and what his intention is. A guy wearing a skirt with a business shirt and tie sends quite a different message than a guy wearing high heels, stockings, a floral dress, make up and a wig. If you live in a progressive area, you can probably get away with incorporating some elements of feminine attire into your everyday wardrobe without any eyebrows being raised. If, on the other hand, you inhabit the regions of our planet where people cling to old values that never existed, wearing women's clothing in public may confuse people to the point of anger.

The important thing to remember is that people respond not only to what you're wearing, but how you hold yourself. A man with his head held high, smiling at the world is likely to experience much more joy in his travels than a man who is scuffling about looking afraid and shifty. Remember, man is a very able predator, and if you make yourself out to be a victim, people respond to that instinctively.

The Eye Of The Beholder

Having said all that, you never know what people are really thinking. For a man leaving the house in women's clothing, he's making a personal journey, but it is a journey that changes every person who lays eyes on him. Though some people might scoff, others may very well be inspired. If the notion of changing perceptions of gender norms just by running to the store for some milk appeals to you, that may be all the courage you need.

Whatever, I'll Do What I Want!

If you have this attitude, then you already have the courage you need to step out looking fabulous in the clothing of your choice, regardless of what other people think of it. A man wearing women's clothing can be considered rebellion against the status quo, and there will be people who love you for it as much as there will be people perplexed or threatened by it.

Inspirational Statement

As I have already mentioned, you don't have to go outside wearing women's clothing if you don't want to. If you do wish to however, and you need courage to do so, think of this. One day, you will no longer have the opportunity to do so. One day all these halcyon years of mobility and existence will have passed you by. Will you come to the end of your life having lived your life in the way that pleased you, or will you have lived your life attempting to please people who don't know you or care about you? When it's put that way, it takes more courage not to go out wearing whatever you want than it does just to do it.


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    • profile image


      8 years ago

      Like cardigansissy, I started out with a few items from the women’s section and subtle fashions. I’m now comfortable wearing skirts in public as well as other obviously feminine clothes. I have even started carrying a purse. I usually make no effort to hide the fact that I am male, although sometimes I like to go in full femme with wig and make up.

      I rarely get comments, and people are often extra friendly when I’m wearing feminine clothes, however last week when running in a really cute running skirt, a drunk guy did start shouting profanity at me and calling me names. I can honestly say, it didn’t bother me, it’s his problem, not mine if he’s so angry about clothes.

      My tips for men who want to diversify their wardrobe are:

      Make sure your clothes fit properly. Try things on before you buy them, not only does it save you from having to return items, it’s a great way to let retailers know there’s money to be made in marketing skirts and such to men. If you are buying more expensive items, such as suits or dress pants, take the extra step to get them altered. I recently took a skirt in to have it altered, and it was no problem at all. In fact, the seamstress seemed excited about how well it looked when I tried it on.

      Dress appropriately for the place/activity and season, as well as age. I know to some it may seem an oxymoron to tell a man wearing a skirt to “dress appropriately,” but I think you will be easily accepted if you wear what the ladies are wearing. I’d love to shop in the misses section, but I just can’t pull it off. Then again, I’m sure many women my age would also love to be able to still shop in the misses section.

      I avoid styles that emphasize body parts that I don’t have.

      Lastly, be confident and have fun. After the first time going out in something pretty, you’ll probably be wondering why you didn’t do it sooner!

    • profile image


      8 years ago

      Your last paragraph is excellent. Life is too short to not be yourself.

      I agree with cardigansissy... be incremental. Start small and work up. Lots of women's clothes, like jeans, are not too feminine and can be worn with no one the wiser. Pick one girly thing, then do more as you gain comfort and confidence. The confidence part is very important.

      So if you have never gone out except as 100% male, pick ONE and do it: ring, bracelet, pendant, women's watch; women's jeans, shorts, belt, top, sweater, coat; purse (one with shoulder strap so you can wear it the guy's way with strap around neck and one arm). Or bra & breast forms, small enough so they're not obvious unless you're really looking closely. You'll see that you CAN do it, you can send out a little feminine signal to all who see you. Then with time you can make the signal stronger. You'll feel good about the world and good about yourself.

      I am now full of confidence being a guy in noticeable breast forms, feminine jewelry, and 90% women's clothes (all but socks and shoes)... in many situations (NOT in certain areas of the city or in blue-collar crowds). But still am not comfortable with wearing a skirt or dress.

    • profile image


      8 years ago

      For any guy who wants to liberate himself from traditional male clothes, I recommend starting off subtly, and moving to more feminine looks as your confidence builds. The women’s racks are filled with clothes that don’t look much different than men’s. For example I often wear skinny jeans and polo shirts from the women’s section, and it is almost a let-down that no one seems to notice I am wearing clothes styled for women. I do think, though, that they are just feminine enough to give people a vague sense that something’s different. If people notice, no one’s ever said anything.

      As you move to more distinctively feminine clothes, I think most people will be pleasantly surprised that most reactions range from arched eyebrows, to utterly neutral to mildly positive. My experience is that most people just don’t care that much. You can “get away” with a lot if you wear women’s pants. I get more looks when I wear a skirt, but I have gone into truck stops filled with only men wearing a skirt in guy mode and not gotten any comments. I also go out in full femme mode, and although I can’t pass as a woman, I haven’t received anything more than curious looks and get more friendly “hellos” than I do when I look like a man.

      As a confidence builder, you may want to pick a friendly venue for your first few times out. You could try the local gay or arts district. I love shopping and women’s departments are generally friendly territory for experimenting with clothes. Once you get out there, you’ll find it’s not a big deal.

      A lot of us imagine that there’s this huge taboo against men wearing women’s clothes, but when you try it and not much happens, you wonder why you thought it was a big deal. Of course, I live near a large city in the US, so results may vary, but I have traveled around the country on many trips wearing only clothes I bought in the women’s department and haven’t had a bad experience.

    • profile image


      8 years ago

      As my wife used to challenge me early on in our marriage, "are you man enough to wear panties?" there is a time and place. Often it is our date nights. I am venturing out more and more.

      I now exclusively wear camisoles instead of cotton whities and it is clear they are silky, feminine camisoles. The only comments I get are from women who compliment me on my pretty cami. I also have come to banish anything inserted in my pockets, so I now carry a purse or black satin messenger bag.

      As I am now in my mid-40s, I don't want to look back with regret that I didn't enjoy my brief time on this mixed up planet.

      Thanks Hope for your wit and perspective!

    • sandeepbirla03 profile image


      8 years ago from United State

      I always enjoy reading your articles. in fact, I look forward to getting the next installment of your perspective and encouragement for men to wear women's clothing. It really helps having a woman's perspective on men wearing women's clothing. I, along with a ton of other men who love to wear women's clothing, appreciate your perspective and support.

    • profile image


      8 years ago

      I started wearing women's cardigans in public, but not extremely feminine ones. Little by little I have worn more & more girly ones out, & am generally amazed that I apparently go unnoticed. I agree that how you hold yourself is key. I have had acquaintances make comments, a male one having a dig asking if that wasn't more something my wife should be wearing, a female one saying it was more like what she would wear, this less of a dig, more playfully winding me up. You can get away with it a bit more if you're eccentric in other ways, not just how you dress. How to get the courage, start with something almost unnoticeable, up it when you want & you'll find your own comfort zone.

    • Hope Alexander profile imageAUTHOR

      Hope Alexander 

      8 years ago

      Yeah, see, dena, you don't get to 'hate' the picture if you want to be a guy wearing women's clothing. It's not cool to judge other people for doing the same thing you want to do in a different way.

    • profile image


      8 years ago


      I always enjoy reading your articles. in fact, I look forward to getting the next installment of your perspective and encouragement for men to wear women's clothing. It really helps having a woman's perspective on men wearing women's clothing. I, along with a ton of other men who love to wear women's clothing, appreciate your perspective and support.

    • profile image

      Szuy 31 

      8 years ago

      The most pointed part of your hub is where you say that one day you may no longer have the ability to go out wearing women's clothing. Recently I was at an academic conference in St. Louis. There were a couple of people I knew there, but it was mostly unknown people from all over the country, including all shapes and sizes of women. Thinking about the various sizes of women I saw, I got it into my head one night that the next day I would dress myself in some ladies' clothes I had brought and I would walk through the spacious hotel lobby to the public parking lot a block away where my car was parked. There I would change into my male clothes and remove my makeup. The next day I got dressed: tan skirt/skort, pantyhose, nylon top, low heels, makeup, wig, and a jacket. When I was finally ready, I chickened out. I sat in a chair for about 45 minutes, desparately trying to work up the courage to leave. I knew there were cleaning ladies outside the door and I didn't want a confrontation the second I set foot out of my room. So I sat and sat and sat, my courage actually decreasing with each passing minute. I had nearly talked myself completely out of it, convinced that this was just a stupid, reckless idea. Then somehow, at the lowest point of my courage and commitment, I steeled myself to walk out that door, precisely because of what you said: I might have an incident if I did it, but if I didn't do it, I knew I was going to regret it big time.

      So I left my room, got on the elvator, and then strolled through the lobby. I'm not small (5'11", 200 pounds), and the reason I got this idea in the first place was that many women attending the conference were on the big and/or tall side. I felt I looked as good as many of them and better than others. My legs are phenomenal, if I do say so myself, even if nothing else about me is particularly feminine. Therefore I felt I had as much right as they did to wear these clothes. I noticed I got a couple of looks from the desk clerks, but I kept walking, right out the door, down the street, and to the parking garage. When I got there, rather than changing and returning, as was my original plan, I got in my car and drove around. When I got back, I decided to try it again, so I strolled through the lobby and back to my room.

      Man, what a rush! I've gone out in women's clothing many times before, but usually at night, often in the comapny of others, and always associated with some club event. This was the first time in my life I ever went out dressed as a woman just for the sake of doing it: no safety net of a final destination where I would be welcomed, and it was just amazing. I didn't want to take the clothes off, even though I knew I had sessions to attend in the afternoon. I kept thinking I should just leave on the skort and pantyhose, but I settled for leaving my makeup on (sans lipstick).

      I don't know when I'll get the courage to do that again, but I hope it's soon. I also kept thinking about your hubs, and I felt I was cheating myself by not going out wearing at least the skort and pantyhose. It also made me wonder if we sell out by going out completely in drag and not having the guts to present ourselves as men to the world who happen to look nice in a skort and nylons.

      My advice is: if you want to present yourself in ladies clothes, at least try it. Will you have a confrontation? Maybe, but probably not. Will you regret it if you don't do it? Absolutely!

    • profile image


      8 years ago

      I really hate the picture. It is the worst. I wear woman's clothes most of the time, most don't care or notice.

      The clothes on the outside reflect what bis going on in the inside ;)

    • profile image


      8 years ago

      Applause for your last paragroph. Life's so so short. Wear silk, satin, denim or whatever tickles your fancy. Just be grateful that your fancy's still ticklish. And don't forget to smile.

    • profile image


      8 years ago

      hi i wear woman's clothing a lot of the time, most of the time just a skirt and t shirt with girls sandals but now and then i go out in a dress that i like along with a nice pair of shoes.

      the hardest part of going out in clothing of the other gender is accepting yourself if you accept yourself then other people will accept you the way you are.

      when i first started to go out in a skirt i believed that i had to try to pass as a woman but after several years i have learnt that people accept me better if i just go out as a man in a skirt than trying to pass as a woman.

      just about everyone i know knows i prefer woman's clothing to men's and no one has any problem with it.

      one thing i learnt is that it is easier to go out to start with in a place that you are not known and that has a lot of people passing through and do not know each other like large shopping centers or country markets.

      the worce places to go out to start with is where there will be many men on there own or in groups after having had a drink as then they seam to think it is expected of them to try to embarrass you or to try to start a fight.

      i belive it is everons right to be able to wear what ever they like as long as it is not indecent.

      regards paul


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