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How To Find The Perfect Woman For A Man Who Wears Women's Clothing

Updated on March 24, 2010
She should be a pirate.
She should be a pirate.

Here's my theory of relationships between males and females. The male usually as masculine as the female is feminine. That's why you see craggy faced, sort of 'ugly' men with pretty feminine women, it's because his masculinity matches her femininity.

What lesson can men who wear lingerie and like to express a feminine side take away from this? Well, that lady who always makes an effort to appear traditionally feminine and makes the most of her female assets? Unlikely to be a good match for a man who likes women's clothing. (Now it is technically possible for a woman who is obsessed with her own femininity to accept a man who wears women's clothing, but in most cases, a man who likes feminine things is going to be barking up a tree that is not only wrong, but actively disdains him.)

It is perhaps harsh, because men who like feminine things are naturally attracted to uber feminine women, but you have to apply a little logic and realize that the uber feminine woman is often uber feminine for a reason, she is seeking to attract an uber masculine male. She's not going to be happy if you try to usurp her role as the female.

A woman who is equally attractive, however puts much less effort into appearing 'feminine' is likely to have a great deal more time and understanding for a man who likes feminine things. In fact, I would advise men looking for women who will love them no matter what they wear to seek out the tomboy type ladies. (These women are, for reasons I'll expound on later, more likely to be genuinely attractive than the barbie doll types you men always, always turn your heads for. You're your own worst enemies, you know.)

Let's face it, if you want her to look pretty and feminine later on, buy her some high heels and stockings and whatnot. It's easier to dress up a tomboy as a lady than it is to get a girly girl looking for her manly man to accept the fact that your female alter ego is called Marcia Jane and she loves candy. A woman who knows what it is like to be forced into a gender role you're not really comfortable with is far more likely to accept your desire to occasionally explore the feminine side of your personality than a woman who thinks that 'men must be men and women must be women.'

So, next time you are looking for a mate, don't ignore the ladies who haven't slathered their faces in make up and aren't doing their best to shove ill covered cleavage in your face. They are the gems in the rough, and by choosing a woman who isn't covered in make up and feminine silliness, you avoid the possibility of waking up the next morning not recognizing the person next to you because she hasn't put her face on yet. A woman who is attractive in jeans and a t shirt without make up on is a woman you'll continue to find attractive for years to come, a woman who needs push up bras, heels, and six tonnes of make up to look 'hot' will quickly disappoint, both emotionally and physically.


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    • thehands profile image

      Jorge Vamos 

      8 years ago

      You could just be "reverse heterosexual," with a girlish-dressing/acting man and a manly woman. Works just as well as the regular kind of heterosexual, I suspect.

    • AntoineAllen profile image


      8 years ago from New York City

      Great hub

    • profile image

      Alana Raso 

      8 years ago

      I'm happy to say that I am the exception. In general, I buy what Hope is saying. The key is to find someone who is open minded.

      My wife is a former model, regional beauty queen and now custom clothier (no kidding). I told her about my attraction to silks & satins, her reaction - "I like silky clothing too!" 23 years later, we are married, have four kids and are planning a remodel with includes a kick-ass sewing studio and over-the-top femme boudoir master bedroom. She would throw me out of the bedroom if I came to bed in anything but silky lingerie. I am very lucky.

      We have discussed many times what makes our relationship work, this is what she says matters:

      1) I had a lot more to offer the relationship other than liking girls clothing

      2) I make her laugh

      3) I tell her I love her everyday, in many ways

      4) When she had a serious illness, I took over being Mother and Father until she could get back on her feet - which she did. Our three boys know how to cook and clean, our daughter is more of a problem.

      5) I make her and the children my top priority

      6) We both give 100% to our marriage, no holding back and ALWAYS be truthful

      7) We are best friends. She likes having a special girlfriend to relate to

      I lucked out as I married a woman who has a lot of integrity, interests and self-confidence. Aside from once being an "it" girl, she doesn't take herself too seriously. She is happier dressing others now, rather than being dressed. She understands that we all have both male and female in our personality. My interest in evening wear & lingerie gives us something to talk about. I sew, I have been a fit model for some of her plus size clients and I help her choose fabric.

      Regarding my interest in lingerie and female clothing. Her attitude is a rather nonchalant “whatever makes you happy.” The only time my dressing has been a problem is when I have been too “needy.” She has been pissed off when I seek approval for dressing, whereas she is just fine having her man in a dress (no matter how frilly) as long as it is her Man.

    • profile image

      Quiet Mouse 

      8 years ago

      As a tomboy very happily married to a guy in skirts the generalization works for us as a couple. He is not treading on my territory one bit and just comes off as a creative guy.

      You are so right, Hope. None better than a tomboy to know gender is *not* in the clothes.

    • profile image


      8 years ago

      Hope, I had an interesting experience yesterday that isn't related directly to your topic, but maybe can contribute to what you are talking about. Yesterday; a college student at the school where I work approached me about donating money for a walk a thon and to actually meet with others for the walk. My schedule has been hectic enough where I won't be able to do the walk, but I know the organization sponsering the walk; so I didn't mind contributing some money. Hope the girl who approached me looks nice, but is more of the tomboy type. Interesting to me is; that the walk is suppose to be done in high heels.

    • Hope Alexander profile imageAUTHOR

      Hope Alexander 

      8 years ago

      You're quite right that it is a generalization, however I have noted a trend. Perhaps a few men can chime in with their experiences?

    • profile image


      8 years ago

      You may be right a lot of the time, but it is a generalization that has many exceptions. I have known women who have "masculine" personalities and who do dress in t-shirts and jeans that are unaccepting of their man's crossdressing, and some very femme women who are very accepting. Also, I have know women who are accepting of crossdressing, but when the guy wants to take it farther (transition? hormones?) they have a hard time.

      Bottom line, everyone will react differently and you may not know right away how they really feel.


      I guess you won't

    • profile image


      8 years ago

      Not to self: Need to look for tomboys:D

      I like those types more anyways. Those are the women I can talk to about important stuff, not just about her new nail polish!

      Thank you for the great advice!

    • profile image


      8 years ago

      I like this.


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