How often would I wear Women’s clothes if I was Allowed?

Today I am wondering about if I would wear women’s clothes regularly if it was acceptable. 

Last year I put up Jess’s Polling Station and have some questions up there and some of you have been kind enough to answer.  The one I want to take a look at right now is the “If it was acceptable for men to wear women’s clothing how much of your time would you spend in women’s clothes?”  The top two answers at 22% each were all of the time and 50% of the time.  The next two were 75% of the time and 90% of the time at 17% each.  With 25% of the time and 10% of the time taking up the remainder.  I find these numbers interesting because it means that 56% of respondents would wear women’s clothing more often than men’s.  If the 50% of the time numbers are added in the number reaches 78% meaning that if a man in dress was acceptable the vast majority of us would wear one half or more of the time.  So I thought I would go through some of the reasons that I would not want to wear women’s clothing all of the time and reasons that I would.

Reasons that women’s clothing is terrible

Pockets – The lack of pockets would drive me insane.  While understand that women have purses to carry stuff in there is still no good reason for the pockets on women’s jeans to be so utterly useless.  The other often stated reason is that women’s fashion is more form fitting and pockets would make them appear bulky.  I am not saying I want giant pockets which I can fit a tablet in but being able to carry a wallet, keys, and phone seems very reasonable.  I also understand that not all women’s clothing is designed to have pockets however a pair of women’s jeans should be able to hold the daily items I always carry with me.

Purses – While some crossdressers love purses I find them quite irritating and having a bag always around and keeping track of it seems like more work than it is worth.  That and women seem to fill purses with the most ridiculous amount of stuff that is not needed.  Not having a purse means I have to keep cleaning out my wallets, pockets, and all the other mobile storage and I see this as a benefit.

Breasts – I love breasts as much as the next guy and I do like to fill out my bra cups however I do not have any of my very own flesh breasts.  The assumption here is that men would be able to wear women’s clothing and fashions without fear; however I don’t think that it would extend to breast forms or implants, at least not right off the get go.  Since I wouldn’t have the right chest to fill out clothing in the right way nor would I have the required cleavage to show off for some of those fashions I would find this frustrating.  Though I suppose if I had breasts then I would have an excuse to wear bras and by extension have a place to put some of my stuff since as I already mentioned the pockets on women’s clothes suck and I dislike purses.

Heels – I am not a fanatic of high heels for a variety of reasons, first things first I am tall for a man and on heels I am ridiculous.  Secondly I have never found them all that comfortable but they are the only shoes that make some outfits look good and for that I may go insane.  So while I can get down with many aspects of women’s fashion I would likely have some issues with the occasional heel usage.

Hosiery – Yes I do like hosiery however there are some limitations to it for instance they are only able to survive a limited number of uses and the cost alone may bankrupt me.

Always changing Fashions – The way in which women`s fashions are always changing and need to be updated all of the time may make me broke and insane.

Jewelry – I don’t wear much jewelry as it is, though I do have a love of watches, I am not clear if wearing women’s clothing would also necessitate the wearing of earrings and necklaces but if it does you can count me out.

Some reasons that I would more than happy to switch my wardrobe over

Weddings – I know what you are thinking but I don’t have a deep desire to walk down the aisle in a white wedding dress, well not much of one at least.  But I really do hate it when I am sitting at a summer wedding in my suit sweating in the heat and the women in their pretty summer dresses looking much less oppressed by the heat.  In those moments I not only desire to wear the dress for the way it would make me feel feminine with the wind blowing the fabric between my legs but also the utilitarian coolness of the wind blowing around my legs keeping me cool and not sweating myself into oblivion.

Hosiery – I may have understated my feelings about hosiery earlier, I actually love it and while hosiery does have some limitations and irritations it would be a serious plus side for me.  The silky smoothness and the different designs always being able to shift up my look with a simple change in legwear, yes please!

Skirts – I do have a thing for skirts even though they lack certain features like pockets or a fly for using the washroom.  Overall I do rather enjoy wearing skirts and the added options to switch up my look would be well worth it.  Not to mention the added benefit of having something that keeps one a little cooler in the heat.

Dresses – I do not have the same love of dresses as skirts but the idea of just needing to put on one piece of clothing and being ready to go is pretty damned tempting and I am not aware of any men’s fashion that is an accepted one piece.  And yes there are some dresses that just scream at me to put them on though I could survive if I was not allowed to wear dresses but could still have blouses and skirts.

Options – While the always changing nature of women’s fashion may drive me insane it would be nice to have the increased options to my wardrobe.  Basically I would be able to keep all of the same men’s fashions and be able to add on skirts, blouses, and dresses to the mix.  Women have more clothing options anyways and combine that with men’s options and I could wear a different outfit all of the time.  I do like to alter my style and try not to wear the same old some old all of the time.


While I am not willing to toss all of my male clothes in garbage and dive in full time women’s fashions if it was socially accepted I would certainly take advantage of it.  Since I do enjoy men’s and women’s clothes I am guessing that I would be somewhere around that 50 / 50 mark depending on the situation.  For instance in the dead of winter I do not see myself wearing that many skirts and while there are women’s pants I might as well take the men’s option.  Though it does bring to mind the question of if I could wear a blouse with men’s slacks? Or a skirt with a dress shirt and tie?  The fashions between the genders are so specific that mixing it up may actually not be a viable option.  While fashion and acceptance are changing in a way that makes it look like this fantasy is on its way I suspect it is not for some time.

Any out there have any other why and why not for women’s clothing?

8 thoughts on “How often would I wear Women’s clothes if I was Allowed?

  1. I love woman’s clothes but don’t think I’d wear them all the time either. For me it’s like a little treat every now and then, albeit a little treat that requires a lot more effort when getting ready. Hats off to the ladies who do it on a regular basis!

  2. Thought provoking article! I must admit I bristle just a tiny bit at the word “allowed.” 🙂

    I present as femme fairly close to 100% of the time, even when I’m not in straight-up crossdresser mode. I’ve never worn breastforms or anything like that — I pick out femme clothes hang well on someone who is very flat chested. I prefer women’s pants — the pockets are bullshit but I think they’re more flattering. To me the purse is such a great trade … before I started carrying one my pockets were always full of crap and I was always forgetting things! Now it just all goes in my bag and it’s all ready to go when I walk out the door.

    There’s a really wide variety of styles in women’s clothing and lots of crossdressers seem to focus in on a very few – and particularly the most uncomfortable ones! Most of my daily clothes are just simple, practical clothes. I’ll wear dresses and heels for special occasions, but a nice comfy sweater and some worn-in jeans with flats can be just as femme. I have plenty of old t-shirts!

    1. Kit I used the word “allowed” as in this case I am not talking about presenting as femme but being a dude in a dress. While transgender is becoming more accepted a guy who just likes to wear women’s clothing is still strangely seen as being totally insane. As for the purse I am fanatical about emptying extra things from my wallet and pockets so the purse is of no use to me. Though I can see why some people use it them.

  3. ahh this is a fun post to consider and I think all of us have. I have to agree with Kit about the wide variety of styles to wear. I can’t think of any occassion I couldn’t find the suitable outfit to wear, whether it be casual or dressy or just being a bum around the house. Womens outfits are far more comfy than mens due to all the stretch and give and the soft materials, if comfy is your goal or dressed to kill for a night at a club… have all the control over the fashion statement you’re making or not. And the winter months offer so many choices of outfits and heels to choose from. Heels? so many choices and comfort levels, just depends on the heel. I find I can wear a decent 4″ wedge heel all day or a 5” pumps for a few hours, depending on the outfit and occasion. The fashion choices really are endless as is your comfort level.

  4. Since I have an understanding wife and I work at home, I almost do live la vida taffeta. BUT, that’s with some limitations: She doesn’t complain largely because I have never shown any indication that I actually want to look like a woman, so breast forms, wigs, makeup, and jewelry are out (although I’m not wild about makeup and jewelry on GGs either)

    Some of your reasons for not wanting to wear women’s clothing 100% of the time seem odd… doing so would not require you to wear hosiery unless you want to! Likewise, if you don’t like heels — wear flats.

    Just by sheer luck a couple of the skirts and several of the maxi dresses I got on ebay do indeed have pockets. Of course since I never actually go out in public wearing any of that stuff, about all I carry around in them are my hands and the occasional kleenex when my nose is runny.

    Kit, I suspect that most crossdressers opt for the “most uncomfortable” choices because there’s a WHOLE lot more going on under the psychological surface than just wanting to feel femme. As noted above, I have no such desire — wearing “women’s” jeans or sweaters does nothing for me; I’m specifically attracted to skirts and dresses, the poofier the better. Why? I have no idea, I gave up on figuring it out after nearly 50 years of self-analysis. But my point is that crossdressing, often “girly” crossdressing, scratches some itch that no other clothing can satisfy, which is why crossdressers often seem to make some odd fashion choices.

    1. I am not disagreeing that there are a wide range of options of what you can or not wear in women’s fashion, It is just that hosiery for some outfits is required, that and I do have a soft spot for it.
      I agree with you on the reason why people go for the uncomfortable girly options, there is just something about it. After all if you are going to go to all of the trouble to violate social norms and gender boundaries you might as well go all of the way perhaps. If we knew the answer though it may take some of the fun out of it.

  5. This is a great post and certainly there many crossdressers who think about that possibility. I changed to women’s clothes most of the time while living as a man quite a while I ago, so if I may i’d like to share some comments:

    Reasons why women’s clothes are terrible: completely agreed, male clothing is much less effort than female clothes. Pockets and purses never bothered me much, wearing a purse gets a habit real fast and you don’t miss the pockets any more. Heels is another story. I ended up avoiding heels as much as I can. Low heeled pumps, ballerinas and mid heels ankle boots are a good compromise and quite comfortable. I would not go back to men’s shoes any more. My current feminine footwear is practical and much more comfortable. Always changing fashion is an important aspect. The time and effort one invests in female outfit once one starts to wear them daily is high. Still, the freedom of having so much more options is worth the effort.

    Reasons why to switch the wardrobe: Hosiery feels nice at first but once you wear pantyhose often you find that it is not the most comfortable piece of clothing. As to skirts, I wear them quite often in particular in summer. Definitely a reason to switch wardrobe but it also takes time to get used to them. When I first switched to women’s clothes in everyday life handling my skirts with grace took quite a bit of practice (sitting in shorter and tighter skirt, taming a long skirt while you walk).

    A few things that are missing in the post: one you are in women’s outfits daily, you have to look the part. Diets and workouts to stay in shape, shaving your legs, manicure, pedicure and hair require quite a bit of discipline that may be challenging if you are not used to it. Make up is another thing that I would list under „terrible“. I found that one you wear a slightly more elegant outfit a little (!) make up is expected even if you don’t intend to pass. Although wearing make up from time to time may be real fun, it take quite a while to get used to it in normal life.

I love to hear from people who read my blog, even if your not in agreement with me. Your comments may spur me on to write something else so please comment.

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s