Why Women Leave Men Who Wear Women's Clothing (Part One)

Updated on January 4, 2017
Do you think 99% of women would leave James Bond because he occasionally wears a bra? Methinks not...
Do you think 99% of women would leave James Bond because he occasionally wears a bra? Methinks not...

This is a tough issue, but I think that it is one that needs to be addressed. It has become obvious that many men who wear women's clothing, both those who wear panties, and those who take their female fashions much further have difficulty sustaining romantic relationships with women. Some men even report losing several partners because of the lingerie, or because of the skirts and high heels.

This article will look at the question why. It's easy to simply say that most women are evil and bigoted and leave it at that, but I don't believe that is true. I think that most women, once they fall for a man, will do most anything to please him, in much the same way a man in love will try his best to keep his special lady happy.

As with anything involving human beings, the issue is complicated, but I have several theories concerning why men who wear women's clothing may find difficulty in maintaining a relationship, and in discussing these theories I hope to also provide some possible solutions.

Problem One | The Hardline Woman Who Refuses To Brook The Mere Mention Of Men In Panties

Women with hardline views religiously or culturally may also have a very hard time dealing with a man who wears women's clothing. To be honest, I think without being too harsh, women who possess hardline views are normally best suited to men who share the same hardline views and values. If a person, male or female, is unable to compromise on arbitrary conditions, then they require either a partner who shares the same value system, or one who is prepared to nod and smile and agree.

Unfortunately, I have a feeling, a hunch, if you will, that men who wear women's clothing for the joy of being feminine and soft and passive, perhaps even submissive are attracted to these hardline women because it is easy to mistake inflexibility for strength. A woman who vociferously and aggressively defends her views may trigger certain responses in a man who enjoys his own feminine side.

So, the man who wears lingerie finds himself dating a string of strong, though inflexible women who, far from indulging his desire for lingerie, simply forbid it, expecting to get their way as they always do.

The Solution

Wean yourself off this type of woman the same way women learn to wean themselves off the 'Bad Boy' type. Yes, domineering women can be sexy, but unless you find one who likes her men to wear lingerie (and there are severe supply and demand issues with that little scenario) you're going to be opening yourself to ongoing heartbreak and guilt as these women reject you and your desires out of hand.

Problem Two | Identity Issues

The likelihood of this problem arising depends on the extent of your dressing in women's clothing. Some men like to wear panties and draw the line there. Some men like to dress up entirely in women's clothing and adopt female personas. Obviously these behaviors sit at obvious ends of the spectrum, and men whose desires tend towards just wanting to have a few pairs of panties about the house are going to have an easier time with their mates than men who want their wives to call them “Susie Snookiepants.”

You have to be honest with yourself, are you the same person on the inside that you portray to your partner on the outside? If your spouse or girlfriend becomes confused about who you are, or worse, suspects that you are simply transitioning to a different gender, she will feel hurt and betrayed. Women want, above all, to understand and to empathize. If you make that impossible, she will not be happy.


If you have an alter ego, introduce your partner to this alter ego at the appropriate time. (The appropriate time being that magical spell in a relationship where you are past simply dating one another, are becoming increasingly intimate and the birds are singing in the trees and under every daisy is a little pot of gold.) Chemically speaking, you're both quite mad at this time, and this is the time where you set expectations and boundaries in your relationship. If you go through this time without letting her see your secret facets, don't be surprised if she freaks out later on.


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    • profile image

      Steve 3 months ago

      I remember my wife at the time knitting herself two 'button to the neck' aran round neck cardigans one in maroon and the other in dark green, both with eight matching plastic buttons down the front. I remember trying on one of my wifes aran cardigans in her absense, I felt great being buttoned up in these lovely cosy cardigans. She also had a lovely long double breasted wool trench coat which I also loved wearing. She eventually discovered my secret wearing of her coat & cardigans and 'freaked out' saying I needed therapy. She is now my ex wife. However I still wear and own a large number of aran cardigans, some unisex, some male fashion. I have many chunky cardigans which are ladies cardigans with big shinny plasic buttons, usually in dark colours, which button on the ladies side up to the neck. I have even found a woolshop where they will knit cardigans specifically for me. I often wear these in public, with a pair of jeans. My present partner accepts my cardigan wearing and I have never received any adverse comments from anyone. I have received some knowing looks and some smiles from females, but hey I'm 65 now and not going to change, I feel great in my cardies and I'm not bothered what other people think.

      The point is I couldn't be happier however now, but it important to be up front and honest in the first place, as difficult thow it may feel at the time.

    • profile image

      Mrs feeling unhappy 5 months ago

      Why will he only have sex with me dressed as a woman? We used to have a good sex life being himself aswell as being "her" ...but now he only wants to do it if hes dressed up ...i dont get it and im feeling really confused and totally un wanted

    • profile image

      Mike 7 months ago

      I'm a hard working straight guy yet I love dressing as a woman and I don't know how to explain it but it has always been there.

    • profile image

      robert hathaway 8 months ago

      im a man who loves to wear womans clothes ans high heels to party on fri and sat nightsand I do

    • profile image

      Matt 8 months ago

      I like panties and my gf doesn't judge me even when I wear the pink leopard spots

    • profile image

      LJ 7 years ago

      If you do some research, you'll discover that in most cultures, (including ours) that pink was originally a boys color and blue was considered girly and frilly. Then along came the nazis and started associating pink with homosexuals and its been linked as a girls and gays color ever since. personally, I love the color pink and have never had a homosexual thought in my life.

    • profile image

      Danielle 8 years ago

      Right said JSG "So, in the end, the clothing market will evolve (and us with it), to the point where men and women will be wearing whatever they want, and no one will care that a women wears a suit and boxers and has hairy legs and man wears a dress and a bra and shaves his legs." I for one have no problem with my husband weaeing panties, nylons and womans shoes which is as far as he dresses on a consistand daily basis. On occasion he will go all out and fully dress with make up and do his hair and nails and I'm ok with that too. After all they are only clothes and him dressing like a woman really isn't hurting anyone now is it?

      It is his preferance and I'm kinda the one responsible for getting him started me and an accident but that is a story for another time. I've always been an exceping person as far as to each their own kinda thinng and I feel that in time it will be ok and maybe even accepted in our society.

    • profile image

      JSG 8 years ago

      Is there really an issue with men wearing women's clothing? Yes. But, this is the way our society is. We, the human population, dictate what is correct attire for men and women, and what isn't. Any variation from this, is considered 'wrong'. If you take some time, and think back several years, it was completely unacceptable for women to wear pants. Pants were considered men's attire. These days, its completely acceptable for woman to wear pants, shorts, skirts, dresses an so on, even mix an match is fine (pants with a skirt). Men, on the other hand, are oppressed and, to an extent, forced to wear only what is considered mens clothing, or be frowned appon, ridiculed, forbidden access, laughed at, killed, etc.

      As the clothing market changes and womens clothing is added to the mens attire (and vice verse), it becomes acceptable for a man/women to wear it, but not before (with exceptions like 'dress up', costume parties, or even Halloween). As an example, it was unacceptable for a man to wear pantyhose, these days, its at the 'OK' stage, and many men wear them, especially in winter. Now, there is a bra for men and mens underwear that look exactly like womens underwear, and I have noticed several where the only difference these have is the tag, the cut, color and style is exactly the same for both men and women. I men 100% the same.

      So, in the end, the clothing market will evolve (and us with it), to the point where men and women will be wearing whatever they want, and no one will care that a women wears a suit and boxers and has hairy legs and man wears a dress and a bra and shaves his legs.

    • LatexLeah profile image

      LatexLeah 8 years ago

      Peer pressure. Fear of discovery. Loss of status. When I, as "Leah", started leaving the house on shopping trips and other excursions, my proclivities, which had been known previously as a "hobby" became a problem.

      Fortunately, nature ran its course and "Leah" faded from the scene. Apparently something had been satisfied and none too soon.

    • profile image

      john 8 years ago

      I was confronted with the freaking out by my ex, eventhough she was the one who initiated that I would try skirt like garments. As our relation therapist pointed out lateron, considering circumstances I had to take over many a part of the tasks of my wife due to her illness. Hence by wearing a skirt also, she had in the end the feeling that I was taking over her role in to many a way, thus eventhouigh she applauded it in first instance, she did freak out (maybe also due to peer pressure)

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      sneakorocksolid 8 years ago

      Hope just deny my comments if you feel they're inappropriate.

    • Hope Alexander profile image

      Hope Alexander 8 years ago

      Hi Lisa,

      Thanks for your comment. I think you have a very good point, no woman should feel obligated to be attracted to anyone for any reason.

      Still, (in many cases) I think it is less like comparing a man not being attracted to a woman in a lumberjack shirt, no make up and a man's hair style to a man not being attracted to a woman wearing a pair of men's boxer shorts.

      You're describing full grown cross dresser behavior, which is a deal breaker for many. I should have been more clear in differentiating behaviors, so mea culpa entirely on this one.

    • Lisa HW profile image

      Lisa HW 8 years ago from Massachusetts

      Many men are more than comfortable with "feminine sides" while also being completely at peace with dressing in men's clothing.

      It is true that's it's all "just clothes", and people should be able to wear whatever they want. Still, I don't think there's anything "hard-line" about a heterosexual woman's not finding men in clothing (that's designed for a completely different kind of body) unappealing. A lot of heterosexual men wouldn't find it attractive if a woman wore a "lumberjack" shirt, no make-up, and a man's hair. style. This is the same thing.

      As we hear time and time again, people can't choose what they're attracted to. That applies to heterosexual people as well as anyone else. This is where the "inflexibility" comes in, but I don't think there should be the implication that women who aren't "ok" with a guy in women's underwear are the ones who have, or are, the "issue". Being "inflexibly heterosexual" in what one finds attractive has nothing to do with being domineering or otherwise "not understanding". I agree with the author that men who want to wear women's clothing should seek out women who aren't "hard-liners" (but I think "hard-liners" is more often about being "at the far end of the heterosexuality scale" than about religious or culture).

    • profile image

      Jakkie 8 years ago

      Women, like men, can sometimes be complicated individuals.

      My feminine journey started at the suggesting and urginging of my ex-wife. Later, she became angry when she learned how much I truly love wearing feminine apparel.

      Oh well, she's gone and I'm still in panties and nighties!

    • profile image

      Mike 8 years ago

      I think people should just be able to wear whatever they want.Its just clothing ! As soon as we are born its pink for girls or blue for boys and that's the problem.As a male I love the color pink on me.So wearing pink panties is normal for me.