Are there Rules to Being a Crossdresser?

Are there Rules to Being a Crossdresser?


We’ve tackled a lot of different topics on this blog when it comes to what it means to be a crossdresser, as well as the many different ways you can crossdress. We’ve gone from talking about how your facial hair should look, what outfits you can wear, and even gone into some societal topics regarding crossdressing. With all these different trends in crossdressing, contrasted with how it has always been, we’ve been wondering: is there only one way to crossdress? Or is it more flexible than that?


We’re coming up in an age where fashion is becoming more and more innovative, and where “breaking the rules” is encouraged when it comes to putting together an outfit. Though crossdressing is just as much a lifestyle as it is a fashion statement, there are definitely elements of it where you can “break the rules”. You can mix up lingerie sets, wear some wigs, and change up what kinds of shoes you wear with your outfits and it could be considered “fashion,” but are you still “crossdressing” if you break these sorts of rules?


I’ve noticed that crossdressing is definitely more specific than any other way of dressing, but in the way I understand it, it’s simply wearing articles of clothing that are traditionally worn by members of the other sex. However, I can also see that “cross dressing” and “being a crossdresser” can be two very different things. Someone who would regularly crossdress might have a set of rules to follow, like staying shaved to appear feminine, and wearing specific outfits that align with the identity of “crossdresser.” On the other hand, someone who is simply crossdressing as a one-time thing, or someone who just enjoys wearing feminine articles of clothing from time to time, might not want the identity of “crossdresser,” as it’s not a hobby that they actively follow. In conjunction with that, someone who is an avid crossdresser could find offense to someone crossdressing as a one-time thing (especially if they think that they’re doing something incorrectly), since being more active crossdresser has a defined culture and lifestyle that comes with it.


Because your opinions are valuable to us, let’s have some discussion in the comments. Is there only one way to be a “crossdresser?” Do you have to stick to a certain set of rules to become one, and if so, what are those rules? Can someone still consider themselves as a “crossdresser” if they break those rules? Give us your opinions! We’d love to hear them!

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Why do we need to label it? Why do we have to choose? Why cant we just flow back and forth between cross dressing and gender dressing? Sometimes its the places you will be that dictate what you can and cannot wear in public. At work, panties and bra and garter under a suit still let you feel feminine. At play, go full on gurl if you want, nobody will care. I don’t see any reason why we need to stick to just ONE way. There are no rules to this, express away in any way you want! But XDress panties are a must (almost daily)!


I have loved reading all these postings. Like many of you, I am a professional, married, and happy to be male, with a strong feminine side. Wearing panties and a bra (yes from Xdress) under my power suite is my way of coping with the stress of my occupation. I am truly blessed with a wife that loves my femme side and buys clothes, lingerie, perfume, makeup and jewelry for me. We love to go shopping together and have girlfriend nights when we do each other’s nails. This all said, I present in a very male way during the day. I have no desire to transition to being a physical female. I am 67 years old with a full beard, and nothing about my outer self says “female”. But on the inside – ahh that is another matter.

I agree with Sheery, regarding rules for cross dressers – “There are no rules.” It really depends on how deeply you identify with your feminine self, and there is no right or wrong in that regard – it depends on your sense of who you are, and everything flows from that sense. I don’t want to sound elitist, but I do believe that those of us who embrace our feminine selves have far more courage and honesty in our self examination than the binary alpha male macho man who hates us and would be violent because of the clothing we choose to wear. Because of such people, we are the most isolated and private of all people. It is interesting to me that we are not even accepted by the LGBTQ community. The L’s don’t accept us because we are male, the G’s don’t accept us because we are femme and not YMCA muscular, the B’s, well they may accept us, but only in a fetishist manner that objectifies us in a sexual manner, the T’s don’t accept us because we aren’t femme enough (as if it were some kind of contest) and the Q’s? refer back to the G’s. As far as general society? Good luck with that one!

Please understand that I’m not whining about the rejection of society – it is what it is, and I wasn’t appointed to govern what others think. This is just the reality of daring to have a sense of self that violates the rules of our society, and isolation is the cost. If there is any rule I would dare to suggest, regarding being a cross dresser, it would be this – dare to be true to yourself, and embrace those differences you discover. In the words of Plato, “An unexamined life is not worth living.” Be courageous, my dear sisters beneath the skin, and celebrate that examination! Thank you, Xdress, for providing us a platform to share our thoughts – and thanks for the great panties and bras!



I’m a 46 year old professional who has a full beard and does crossfit. I have no desire to go out in public or transition in any way, I just love the feel of panties and lingerie when I’m home with my wife. She was curious in the beginning about a lot of things in regards to our relationship but she loves seeing me in my outfits now. We do some role play here at the house and are always open to trying new things together so I think outfits definitely help bring that out of us.


I am an older professional gentleman that just started crossdressing in panties. In actuality I am not really crossdressing because I am buying and wearing panties made for men. Society labels everything and you just have to love life and live it to the fullest. Most people grow up with “this is what men wear and this is what women wear”. Churches teach it, schools teach it. Parents teach it. Although my wife loves what I wear and calls my panties my fundies I could never tell my grown children. I would likely be banned from seeing my grandkids. And heaven help me if my construction co workers found out. Most if not all men have a feminine side just most of them choose to hide it because of what society might think. Recently I had a Doctors appt and wore a pink frilly sexy lace thong, I’m sure the nurses had a good conversation when I left but I decided they don’t make decisions in my life. I do. Now that I have discovered that wearing frilly, lacy, sexy panties in traditionally women’s colors is exciting and sensuous to me and my wife all of my boxers are going away. I am never going to wear traditional men’s underwear again.


I love this conversation. It has so many levels.

I think there can be as many different types of crossdressers as there are crossdressers. For me, the inclination to dress in women’s clothes comes and goes, but I always wear women’s underwear, and frequently wear women’s jeans and shirt/top. The jeans/top combination is what it is, and doesn’t “look female,” so I don’t know how that would/wouldn’t qualify. Our culture has ingrained in us too many added fashion rules that we tend to forget the first and most important one: be yourself.

All that said, I don’t mind the label. Sometimes, yeah, I do wish I was born female, or was female-bodied . . . smaller frame, smaller feet, lighter voice. But I can’t change these genetic things about me. So I make-do with what I have — with who I am. And if wearing women’s clothing helps ease the anxiety brought about by my natural state, then I’m going to wear panties every single day.


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