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!


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)!

Scott October 21, 2020

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!


ANGIE March 29, 2018

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.

CHAD March 29, 2018

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.

ROLAND March 29, 2018

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.

JO March 29, 2018

I just turned 50 last month and my first pair of panties were traded from a little girl I had a crush on in third grade. She wanted my briefs and after She saw me peeking at her pretty flowered panties she offered to trade. I lept at the offer and in the process had my first show me yours I’ll show you mine session with a girl. I wore her panties home that day and she gave me “girl tips” for the next 3 years. I was an effeminate boy. Today many would say that I am a cross dresser as I am in clothing that is female most days all day. I do not however try to appear to be a female or “pass” as they say. I am a 6’ 2" muscular 220lb bald man with a beard, I don’t want to look like a female or be a female. I just like to feel pretty and sometimes like to play French maid or cheerleader with my wife of 29 years. I do wear skirts and flowered shorts as well as frilly stocks (especially with lace ruffles) out and about. I wear one of my one piece swim suits to the pool to swim. I have been called out at a local gay/transgendered/transsexual bar for being a fraud or fake but I am just being me. I may be somewhat of a sissy at times but I am proud to be a man. What’s wrong with that? Nothing, it should be about letting everyone be themselves and express themselves as who they are not be judged according to a stereotype.

CHRIS March 29, 2018

There is definitely not ‘one kind’ of crossdresser. What people define or characterize as crossdressing varies widely. As a teen, from the time I started buying my own underwear, and into my adult years, I always preferred wearing unconventional men’s underwear. Underwear that by today’s standards, were cut and styled, and made of fabrics such as silk and nylon that were more typical of women’s underwear. I preferred bikini styles, and liked prints and colors that often were only available from places that sold ‘fashion’ underwear for men.
No wonder then, that I eventually began to shop for underwear in the women’s lingerie department. My first pantie purchases were rather simple, unisex styles in solid colors. As time went on, my selections became increasingly more feminine looking. Today, about 15 years after starting to buy panties, women’s underwear is all I wear. I have about 150 panties, no two alike. Compared to men’s underwear selections, the variety of styles, colors, fabrics, prints and patterns available for women is endless, and constantly changing. I love the variety, but I also like the look and feel of the softer, silkier, slinkier fabrics. But, AND THIS IS AN IMPORTANT DISTINCTION, panties are the only garment I wear that is distinguishable as one made for and marketed to women. I really have no desire to cross dress into other feminine attire. I have no interest in wearing dresses, stockings, bras, or slips. I don’t wear makeup or wigs, and have not adopted a feminine name like Stephanie, for instance. I do own, and wear a few other pieces of clothing like tights, gym shorts and bathing suits that are women’s, but they are not so feminine in their design that they are easily recognizable as a woman’s garment.
My wife of nearly 32 years knows that I have a major affinity for panties, sees me in them everyday, and knows that panties are what I wear as underwear, every day. We buy them for each other, and have several pair that are a perfect match. I am a business professional, and very masculine. My weight is in proportion to my height, and I think I look great in panties. I find men’s underwear to be rather homely looking, and they do not fit well.
I wear panties, but I don’t consider myself a crossdresser. In fact, some of the crossdressers I have met, and have corresponded with are rather dismissive of my preference for panties, or the fact that any other women’s clothing I do occasionally wear is ‘unisex’. I’ve been told that I am a latent crossdresser, and that someday, I will transition to wearing other women’s garments. There doesn’t really seem to be a category that men like me ‘fit’ into…men who like wearing panties made for, and marketed to women (or made for men, like those sold on XDress and BodyAware), but have no interest in crossdressing, or being concerned about whether or not they can ‘pass’ as a woman.

STEVEN March 29, 2018

Since society’s “rules” make crossdressing such a secretive and potentially shameful act for many of us, it would be nice if crossdressing itself could be a rules free zone. :-)

I do like that you acknowledged the full spectrum of men that like to crossdress. Personally, I’m a masculine man that just likes to wear lingerie from time to time. Although I’ll concede that some of my xdress panties are far more comfortable than any mens underwear I own, I typically only wear them if I’m going out with my girlfriend. Essentially like many women do, I’m wearing my nicest panties when I think I might be getting lucky that night. haha

I don’t really identify with those that are fully into crossdressing as a lifestyle, or those that create a female “persona” for themselves. Don’t get me wrong, I’m not judging those people. Nor should they judge me. We should all be nothing but tolerant of each other. Some standard fashion guidelines might still apply though. Such as try to wear items that are flattering to your body type. Haha

SR March 29, 2018

I considere a cross dresser just in some cases when I want to feel sexy and being watched for men. I dress up just in the nights and I go out walkin down the streets showing my lingerie but in the mornings I do my normal life wearing men clothes. I have a short time doing this but everyday I want to wear new women clothes.


ADDAN March 29, 2018

Of course there is no one way to be crossdresser, maybe there are as many as us.
Me for example I use lingerie every single day since more than 30 years ago and I use my “normal” men cloths and under my bra, slip, even suspender and socks.
Sometimes in a special circumstances I crossdress me totally not just my underwear and then I use a dress a wig and make up.
By the way, I’m married with a woman and both of us enjoy this.

CARLOS March 29, 2018

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