Wearing Women’s Clothing vs. Dressing Like a Woman

Big difference. I frequent a popular CD forum and read all kind of things, some I can relate to, some are touching and frankly many are simply silly, a few creep me out. One thread got me thinking. Someone posed the question as to what everyone wears while lounging around the house. She went on to say she was wearing a nightgown and pantyhose (and in typical CD fashion, she referenced the specific brand of pantyhose as well as a very detailed description of the nightgown). And that is the classic example of “wearing women’s clothing”. There is not a single woman on this planet that would wear a nightgown with pantyhose.

I have certainly had my time wearing articles of women’s clothing, often in combinations that made zero sense. I now dress as a woman would. There is a tremendous difference in the two. If you want to go out in public, if you want to be accepted by mainstream society, if you want to feel like a woman does, then “dress like a woman would”. Do not just throw on things because they are female attire.

If you have a woman in your life, observe her. If not, take a look at the many women that walk our planet. Make mental notes. Be observant. What are they wearing? How to they combine different things? Is their blouse completely tucked in or partially tucked in the front and loose in the back? What is the length of their jeans and what type of shoes are they wearing with those jeans? What are they wearing over their sweater? Woman generally do not like wearing pantyhose. They generally go barelegged in the summer.

When I watch TV, I notice different types of necklaces (Hallmark movies are great for this) and how they work and with what. I pay attention to how things are combined. I am a sponge, trying to make up for the years I was aching to be, but not able to be for many reasons, the woman I have become.

This also goes for makeup. Watch, observe. Go to a makeup store and seek advice. Ask questions. Learn. Watch YouTube videos. Don’t walk out looking like Mimi from The Drew Carey Show (Google it if you are not familiar).

If you take this seriously, meaning you want to be treated by the public as a woman, then show some constraint and dress like a woman. Invest in your presentation, and I mean in terms of time, study, observation, learning and the use of good judgement. Slow it down. We all know the thrill of this (and there is an undeniable thrill to this), but do it right and you’ll reap much greater benefits. Just because you are wearing women’s clothing does not make you a woman. There is a difference. Dress like a woman, ladies!

PS For anyone new to Kandi’s Land, we operate under one basic premise here. This is not simply about “crossdressing”. I am not transgendered as typically defined. I consider myself bi-gendered. This is about presenting myself to the public (going out in public is THE key component of me) as a woman. That means I wear generally what a woman would wear in the situation I place myself. So, you will see me in dresses, skirts, blazers, sweaters, jeans, leggings, basically the broad pallet of what real woman might wear to go shopping, to the museum, to church, etc. In other words, this is all about dressing like a woman. Many other blogs cover wearing women’s clothes and do so much better than I do.

19 thoughts on “Wearing Women’s Clothing vs. Dressing Like a Woman

  1. The great thing about dressing as a women is the variety in what to wear, from the dressy dress to the down right just very casual jeans and a tee.
    For me I’m primarily a causal women as when I go out I’m doing basic things like shopping or buying gas and it works for me and it makes me happy
    Like you Kandi I don’t pass my body type has to many tells but I just show as much confidence as I can a show all that I’m just me


  2. Kandi, I agree with you. I want to look like a woman, not wear the clothes of a woman.

    But around where I live women only wear slacks, jeans, track pants, sweaters, T-shirts, running shoes or boots. They never/rarely wear a skirt or a dress. Occasionally they might wear a blouse.

    I wanted to buy a mid length skirt, so I visited four local towns and shopped in the department stores. None of the stores sell skirts or dresses. The stores know the local clientele; real women don’t buy skirts or dresses. It’s all jeans, track pants and slacks.

    I would have to go to the really big city, downtown, (or a fancy party) to fit in if I was wearing a skirt or dress.

    So sad. I joke that the best way to dress like the modern woman, is to dress like a man.



    1. This is very true – most women dress extremely casual most of the time. This is one of the reasons I love living in the city, there’s always someplace where it’s not totally out of place to be dressed a bit fancy.


  3. I mostly agree, but am a little uncomfortable with the phrase “dress as a woman would”. For me, it might be more accurate to say, “I dress to express my style”. I try not to impose gender, even though society probably does anyway.

    Let me say it this way. I consider myself to be just like everyone else in the world. On regular days, I wear casual comfortable clothes for work, errands and doing all the mundane things of life. However, if I’m doing something fun or interesting I will wear something special, something that makes me feel pretty and gives me a little extra confidence. The only difference between myself and most of the world is that my casual clothes are from the men’s department and the special occasion clothes are from the women’s department. So, it’s not so much that I’m trying to dress like a woman or be an imitation of a woman, I’m just trying to dress like me, without really thinking too much about gender.

    The big revelation that got me to this place was to learn to accept – and even celebrate – my uniqueness. I should add that my thoughts on this subject are not static and are constantly evolving – the reason it’s called a journey.

    Liked by 1 person

      1. I think what we sometimes forget is where we were in the past. For decades I dressed only at home and had my far share dresses that were too tight and too short. I also did the pantyhose under a nightgown thing and even go back to it once in a blue moon. I have definitely evolved, but not everyone else has the freedom of being out at home or the time and treasure to invest in perfecting their look. I try to remember that everyone’s journey is unique and every journey is special and beautiful.

        The thing I see too much of, especially on Facebook, is cringe based judgement. The inclination that a member of our community is making us look bad because they present in a way that makes us cringe. (The ‘cringe’ terminology is from a ContraPoints video https://m.youtube.com/watch?v=vRBsaJPkt2Q)

        Rather than scold our community, we should be pushing society to be open to all forms of expression, even those that make us, personally,uncomfortable. IMHO, pushing the boundaries is the way to gain true acceptance, regardless of where an individual is at on their journey.


      2. I hope my post wasn’t interpreted as “scolding”. My purpose here is to speak to those that wish to go out in public. If one wants that (okay, if not, of course), than I hope to give them something to think about. Dress like a woman to go out there, if not, do whatever makes you happy. I have discussed here in great detail the things I did for the first 50+ years of my life, throwing on this or that just to quell the urge.


  4. I have several lovely evening gowns and now there is virtually no place to wear them because most women are “dressing down” and I would be out of place for looking nice


    1. You can always dress as a stylish woman, never be afraid of that. My point about going out is that you wear things that women would wear, IF you goal is to blend in. What one wears to make themselves happy is quite alright, I just speak from the prospective of one who attempts to go out unnoticed or noticed positively. All of us that dress opposite their birth genders are snowflakes and it means something different in different ways to all of us.


  5. Kandi

    Another good piece of common sense particularly for the GAL just beginning her adventure. Take it slow, be observant and learn . Completely agree with you and would add one small item develop your own inner sense of being a “female” . This is a vital part of the road to full to your personal satisfaction and fulfillment and I allows one to enjoy both sides of aisle.

    Marie Anne


  6. I always strive to dress as any other woman would in a particular setting. If i’m at the outlet mall on a Saturday afternoon, its totally casual. At a nice restaurant on a Saturday evening I will wear something dressier. I really enjoy both, but in any case, my goal is to blend in as a woman to the best of my ability.


  7. re; most women do not wear pantyhose in the summer–true-but if many women of all types would take a good look at their bare legs in a mirror they might have second thoughts. here in Florida it is usually summer most of the year and I must say ugh! (yours truly included)


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