I want to go in public as a man in a skirt --- advice?

To be honest, the bottom two are the most workable in my book. The blouses in the top three is a bit too much, especially if going out for the first time. The jacket in the bottom right may be a tad to "feminine", though in my eyes it looks great, I would lose the forms entirely, you are going for a man in skirt look, or an androgynous look. Men do not have shapely breasts:) At most men have moobs, and they are not viewed at in a positive manner. I am just looking at this when it comes to your comfort level.

Comfort is really the key. Take my forays of late. Last weak I did not wear pants the entire week. Every day I wore some type of legging. At first it was in an athletic look, and flat black leggings, and low boots. The next day I donned my disco pant, rocker shirt, tall combat boots, and loose shirt. The next day I was more daring. I wore my dark blue leggings, with my combat boots, gray t shit, with a dragon motif. Thursday, The shiniest pair of black leggings I have, low ankle boots, nice dress shirt with a belt, so it formed a tunic. Then Friday I wore a more athletic style, with my white sided leggings, tennis shoes, and t-shirt

All of these either drew no comment or some kind of compliment. But as I said a key fact was my own comfort level. I do not quite have the courage to wear a skirted outfit quite yet, but I do not count the possibility out.

Your looks are descent, and if this world were not sexist, they would be fully acceptable. I am very partial to the lower left the more I think about it.

Because of your beard especially, I would suggest finding a way to incorporate a couple more masculine flourishes to blend in with the feminine so that your overall look feels more balanced. I too would suggest losing the breast forms as right now the look is leaning less toward "man in a skirt" and more like "man's head on woman's body."

With your current presentation though, the look that is working the most in my opinion, is the dark jacket with the grey skirt. The big reason I say this is that the jacket appears fitted, which is a good combination with a full skirt like that. With tough love honesty here, I feel like the white shirt, which is a little loose, combined with the long flowwy skirt, has a general frumpiness to it. The picture with the jacket on the other hand gives you a sleek silhouette and also feels just a bit more contemporary.

Like Pythos said though, the most important detail is your own personal comfort with things.

Yes, the forms are going for sure. Those photos are just pre-edited (before I lob off my head!). While I personally like the black jacket and grey skirt best, I've put on some weight and the "frumpy" look of the others is- because I'm frumpy looking at this weight!

I'll choose the plainest blouse I have, likely even a man's oxford.

It looks like it's going to be raining while I'm traveling, so a rain coat is probably going to conceal a lot of details from the waist to the neck.

I like all of them :)

My vote goes to numbers 1 and 4

You could always wear a Kilt....

The one with the green skirt, possibly influenced by the shot - you look more relaxed and comfortable in it. It just gives the impression that it's you.

As the others have said, it's ultimately about your comfort level, and that's what will shine through as confidence when you're out.

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Originally Posted by annecwesley

Yes, the forms are going for sure. Those photos are just pre-edited (before I lob off my head!). While I personally like the black jacket and grey skirt best, I've put on some weight and the "frumpy" look of the others is- because I'm frumpy looking at this weight!.

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I highly highly recommend picking up a women's style guide. One that I found extremely helpful was this one from Glamour magazine. The reason for this is that the very purpose of a book like this is to help you learn how to dress for *your* body shape, to play down the bad areas and play up the good areas. This will require a little extra work on your part because you then have to add the extra step of figuring out what a "male" equivalent to some of the stuff would be, but it is an excellent starting point for figuring out how to dress your body with all of the expanded wardrobe options you're giving yourself.

The reason I say this is because I absolutely think the frumpiness aspect comes from the combination of the loose shirt with the full skirt. It's one of the first "Don'ts" that you'll find in the book, and you will be amazed at how different your body shape can look with the right clothing choices.

Well I did it, and I quite enjoyed myself. It was quite an experience and I'll post some more about it later.

Good for you! Look forward to reading about it

i do not know about waring a skirt when in male mode. but i always have a pair of skinny jeans on. some plane pockets and some with a bit fancer on the pockets. but no sequins or really girlie pockets. but it is nothing for me to be out with only womens clothing on (again not girlie) and nobody notices...or at least has said anything to me.
i spend most of my time in womens clothing (no wife or gg friend), only time mostly male is at work, required uniform.

have fun and watch your 6.

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Congrats! Also can't wait to read about it.

I've posted a note about my time out, including a picture, in the photos section. I quite enjoyed myself, learned alot, developed some courage, and amused a couple people I'm sure.

Everyone, of course, is free to do as they choose. But I have to keep it real here...
I believe there are very few parts of the USA where (other than a scottish kilt situation) a male won't be looked upon as a freak if he's wearing a skirt. If you're ok with that, I say go for it. It all depends on the individual and how they handle their interaction with society. Sorry, but I don't believe it will ever be the norm for males to wear skirts in public.

In my humble opinion----------STAY HOME---------I agree with your right to partially dress--------I question your taste. This kind of behavior makes it more difficult for those of us trying to make our way as females.

If your beard is a problem shave the damn thing off.

I know this will P O a bunch of people but it is my opinion and you asked for my (and others) advice

Susan in Phoenix

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Originally Posted by susanwill49

In my humble opinion----------STAY HOME---------I agree with your right to partially dress--------I question your taste. This kind of behavior makes it more difficult for those of us trying to make our way as females.

If your beard is a problem shave the damn thing off.

I know this will P O a bunch of people but it is my opinion and you asked for my (and others) advice

Susan in Phoenix

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If you can pass as a female then why does my dressing in a skirt make things harder for you?

Believe me I do admire the men here who can pass as women and wish I could have that casual freedom to enjoy my preferred clothing styles.

My entire life is not about wearing women's clothing and trying to look like a woman. Even if I shaved my beard I doubt I could do more than go out looking like a man trying to disguise himself as a woman. I'm trying something honest and open and unambiguous.

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Originally Posted by susanwill49

In my humble opinion----------STAY HOME---------I agree with your right to partially dress--------I question your taste. This kind of behavior makes it more difficult for those of us trying to make our way as females.
If your beard is a problem shave the damn thing off.

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I agree with this.
A guy wearing a kilt in guy mode is one thing. A guy wearing a clearly female skirt, shoes, with facial hair, etc. in guy mode is something else entirely.

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Originally Posted by Pythos

Advice?
Seriously though. I usually wear a long trench coat when in a short skirt, when on my own. But if in the company of friends, especially female ones, I have my legs completely visible.
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Hmm ... bare legs with a trench coat - that sure looks like a flasher not in action . :):):)

I can't see any of the pictures above, but I see no problem with simply wearing a skirt. I blend women's clothes into my wardrobe. I don't try to pass, maybe one day I will try, but I go for more of the androgynous route myself. If a skirt looks good I wear it. Surprisingly, most just don't seem to care. If it obviously looks weird - don't wear it. If the outfit isn't over the top and looks good, wear it.

However - if you wear a skirt with a beard - that may not match very well, unless you go the masculine route and wear a kilt.

I think this thread revealed some real ugliness. My God I could not believe some of these posters want to have the freedom to dress as women, and yet put down a guy with the guts to do as women have done for years...integrate clothing items of the other gender into their style.

Oh and the trenchcoat/ flasher reference was HIGHLY unappreciated due to the fact you were going by sterotypes. But what should I expect from someone that is as mean to someone trying something different as you.

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Originally Posted by JenniferB

Sorry, but I don't believe it will ever be the norm for males to wear skirts in public.

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I think it is getting to the point where it is not the norm for anybody - women included to wear skirts in public.

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Originally Posted by Pythos

I Oh and the trenchcoat/ flasher reference was HIGHLY unappreciated due to the fact you were going by sterotypes. But what should I expect from someone that is as mean to someone trying something different as you.

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I was not trying to put anybody down. It was an attempt at light hearted humor. I have worn a trench coat with shorts, and someone said "you look like a flasher" and I laughed.

John H. The humor missed me. Sorry about that.

I don't like us CDs, or fashion deviants being linked in any way to true sick deviants. Flashers, Child molesters, rapists, and so on. I want our group so far un related from one another it is not funny.

My trench by the way is Sooooooo far from the kind usually depicted as being worn by flashers :)

I think your humor was missed due to the level of ugliness by certain posters here. As I stated earlier, I could not believe the ugliness of some of the comments made.

John H. The humor missed me. Sorry about that.

I don't like us CDs, or fashion deviants being linked in any way to true sick deviants. Flashers, Child molesters, rapists, and so on. I want our group so far un related from one another it is not funny.

My trench by the way is Sooooooo far from the kind usually depicted as being worn by flashers :)

I think your humor was missed due to the level of ugliness by certain posters here. As I stated earlier, I could not believe the ugliness of some of the comments made.

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Originally Posted by JohnH

I was not trying to put anybody down. It was an attempt at light hearted humor. I have worn a trench coat with shorts, and someone said "you look like a flasher" and I laughed.

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I actually thought it was rather amusing, but some people are totally incapable of recognizing humor. It happens.