Wearing Women’s Clothing vs. Dressing Like a Woman

Points I made a few years back, for your consideration today.

Big difference. I frequent(ed) 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. Have a plan, think things through.

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!

Check out this worthy case: https://tobefree012.blogspot.com/2024/05/welcome-to-tobefree-blog.html

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15 Responses

  1. I completely agree with you Kandi.

    If I had some fashion sense I would look even better. My wardrobe is limited. But I am happy with my style, it is me.

    I do try to learn from your example.

    Thank you.

    Jocelyn

  2. Hi Kandi,
    I certainly agree that a person should “wear what a woman would” if they truly want to blend in the real world. But I don’t see anything wrong with having some time to wear whatever one wants, regardless of appearance. I also often lounge around the house in a satin nightgown and pantyhose (and sometimes even my stilettos) because they are items of clothing that bring me comfort…although I’m sure I must look like I’m in an episode of 1980s Dynasty:)

    1. Elise, Please understand I never said there was anything wrong, just apples and oranges. My site comes from the perspective of someone who does wish to blend into society, so I will always view things with that lens. Thank you for your input and for reading my blathering… ❤️

  3. Kandi,
    We must accept not all go out to emulate a woman , they want to be noticed , the question that poses is , ” What as ?” but they are free to make those choices .
    I totally agree with your post but it needed the final push to go fulltime before it all came together for me , suddenly being faced with ” EVERYDAY ” what do you wear ? Going out to social trans meetings can often mean OTT so now I had to learn how little rather than too much to integrate into everyday society . This doesn’t mean being lazy , cutting back on the basics , the prep work still needs to be done , as you mentioned in another recent post pictures don’t show the hard work behind them , it doesn’t come easy some days .

    While we often set our stall out by watching how women do it we mustn’t foget they get things wrong sometimes , the important thing to learn is dressing for your body shape , certain fashions ideas don’t work on everyone , a loose fitting blouse/top on one person can look like a tent on another . Many women hate some part of their body so look for cover ups , I’m fairly happy with my shape , so I tend to wear things that suit me rather than covering up parts .

    The other question is do we or should we dress our age ? I’m not tall for a guy at 5′ 7″ but reasonably tall for a woman , my hemlines tend to sit on or slightly above my knee , it doesn’t over concern me because my legs are OK but many women of my age are wearing calf length hemlines which I personally don’t like unless it’s winter wear with boots .

    The bottom line is if you finally make the decision to go out in the RW and wish to do so on a regular basis then try not to dress to be read easliy , it’s so hard to get over knock backs .

  4. Hi Kandi:
    Since my earliest days of active crossdressing I have been a disciple of your approach to going out into the community. Unless you desire is to stand out, blend in-with style. I have tried to be observant of the women around me and dress to the situation I find myself. However, I find that many if not most of us crossdressers must exert more effort in order to truly do this. For me that is in the area of makeup. In the safety of the Keystone Conference this year I experimented with less than my usual makeup for the more casual situations, as any woman might. There were many candid photos taken at this time, and I found there was way too much male me showing through for my personal comfort. I prefer to present as one gender or the other rather than a blend. Thus, my next goal to refine my presentation is to develop a feminine makeup style that blends with the lesser makeup style women wear in casual situations. It’s going to take some more research and experimentation , but hey, for me that’s part of the fun!
    Best,
    Kris

    1. Thanks so much Kris! Makeup is the key and it is part of the journey. Prior to Kandi in 2014, I had a moustache for my entire adult life. I don’t think you see it because I have developed my makeup skills, but I see it because it always used to be there. Get better every single time out!

  5. Kris,
    I found it helped with a trip to my Boots outlet ( I believe the company is owned by a US company .) and ask for a skin colour check so I could get the basics correct . Once the beautician had analysed my skin colour she showed me how to apply it and then followed on by taking me on a personal shopping trip around the various manufacturers to find eye and lipstick colour to match my foundation . I never go out without makeup , my usual is lining only the top eyelid but not the lower ( a tip from a GG after she showed lower lining actually makes eyes look smaller . I have blue/grey eyes so use shades of biege/brown for eye colour and always a coating of mascara . My usual lipstick is a soft pink always applied after I’ve lined and filled the lips with a pencil , another tip for more mature ladies is use peach coloured blusher rather than red/pink and I finish with powder to fix it all , this usually lasts me all day . We don’t need to go OTT but I feel our face must achieve a balance , our lips attracting as much attention as our eyes .

    I agree we cannot go out natural , I personally wouldn’t feel comfortable and confident , it’s been six years now so I must be doing something right .

  6. Dear you are so right as usual! I’ve had my best acceptance in jeans and a nice top. Woman’s clothing offers so much more variation than men’s and it’s fun to mix and match!

    XO to all.

    Lynnelee

  7. Hi Kandi,
    Thank you for this post. Speaking generally your comments are bang on. I don’t honestly know how women dress typically in the States. I’m thinking it would be similar to Canada. But I’m finding women up here do not dress as femininely as they used to not that long ago. Other than the larger centres I’ve found that a lot of women wear very little make up if any, T shirts, jeans and sneakers. If I truly wanted to blend in with a lot of women in my town all I’d need to wear is my wig, maybe ear rings, sneakers and some mascara the rest would be my typical guy clothes. But to be easy on my town the main industries here are farming, ranching, mining and forestry.
    But if I’m down in Vancouver it’s totally different. There are a lot of women there that dress like they do in my home town but the majority still dress as attractive women. Even in Kelowna which isn’t far from where I live and a bit bigger a lot of the women there dress more like they do in Vancouver too.
    But Kandi do you find girls south of the border find the girls south of the border are like this as well. I know you are fairly well traveled. What do you think?

    Trish ❤️

    1. Trish,

      I was drawing the distinction between dressing like a woman (which I strive for) and the simple act of wearing women’s clothing. Nothing wrong with either one, they are apples and oranges, so to speak. But they are indeed very different. Many things go into how women dress in any particular region and even within part of that region. When I am downtown, a casual dress is commonplace, because there are more working women vs. women out and about. Weather, time of day, location, venue, season, day of the week all factor in. And this is the joy of being female, all the options!

      Love you,
      Kandi

  8. Kandi,
    You got to dress appropriate, be sensiable.
    I wear women’s clothes as a woman would.
    I blend both sides of me as much as possible. I live in both worlds simultaneously. I have NAILS 24/7 and I wear heels all the time. There is no hiding either of them in male mode. On the flip side, I have real reasons to have acrylic nails and raise my heel 4 inches. Why not extend that to include exquisite nails and stilettos. (Girls Just Wanna Have Fun – Cyndi Lauper)
    My women’s clothes are taking over my walk-in closet. I wear them as a woman would. One of the few regions of male clothes are my (summer) tops – Hawaiian and linen dress shirts. Once it starts to chill down here, it will be back to my bodysuits. I lounge around my house in a cami (with or without a bra) either in shorts, leggings, or bikini bottom; like a typical woman would. I wear leggings in public to run errands all the time.
    My real weakness is mascara. Many times I will apply it on my days off.
    Cali

  9. Good advice and observations Kandi
    I sometimes get confused, do I actually want to be a woman or do I just love wearing the clothes. Maybe it’s both! I’m still working it all out 🤔

      1. Thanks Kandi , it’s nice to hear other people’s thoughts. I’m glad we are all in it together, it’s so much better than going it alone 🙂

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