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

[annecwesley]

I'm going on a business trip, a long drive from home. I plan to make the trips to and from all day "dress and drives". I'll make a few stops along the way - depending on how bold I feel at the time I'll stay dressed. I'll have to stop for gas and coffee, I'd like to do a little shopping, sit in for lunch along the way, maybe do just a little sight seeing etc.

Unfortunately, because I have a beard I can't even try to pass. I'm going in public as a man in a skirt and pantyhose - which I've never done before. I will try to be otherwise inconspicuous, at least to the degree that I won't wear spike heels, fishnets and a micro skirt! I know I'll draw some stares and glances, but I want to do this, and I feel that I can do it with some confidence and simply enjoy the feel of my favorite style of clothing for the day.

Any advice?

[Dian077]

I have been wanting to do the same thing. I have not been able to bring myself to do it yet though.
I had been thinking that I would wear something like a just above the knee skirt, something close to a kilt, with a matching shirt with no forms and a nice pair of flats....Thats just me though

[LeannL]

A couple of weeks ago, I saw two guys in skirts in two different cities on the same day. The first was in San Francisco waiting in line to change his flight. He had on a plaid skirt with pleats but definately not a kilt. He did not have women's shoes on. The second was in Dallas and he was wearing a utilikilt. So if you have a skirt that could sort-of-be a kilt, that would be more believable and may make you more comfortable.

Leann

[bobbie anne]

I have done this a few times. I have a just above the knee kahaki skirt that could pass for shorts unless you look closely, I have stopped for gas and so far no one has noticed or said anything. I alos do not present myself as female. Just a guy wearing a skirt

[Emma England]

I have lost count the number of times I have worn a skirt as a male.

It started 4 years ago during the summer. It was simply too hot to wear jeans - and I don't like the look of shorts.
A skirt is more stylish and cooler than shorts.

I think it is very hard for most of us to pass as women. It is much easier just to stay a male but wearing womens clothes.

People do not stare or make any comments at all. In fact the non-reaction is much the same as if you were to wear pants - no big deal.

That last sentence is the advice from me. Treat skirts the same as pants. What are you scared of? A piece of cotton wrapped around your legs?

Oh, look at my signature - it is very appropriate for this thread!

[annecwesley]

What about hosiery and shoes? I wouldn't feel dressed without a slip and pantyhose, and my guy shoes are just too chunky for exposed legs.

[Tracy X Cruz]

I do it very very often my self and I just dress up completely and really forget that my voice is deep and my face unshaven.

The best advice I can give you is CONFIDENCE!

Do not make it look like you are guilty, scared, or whatever. Act normal do things normal. No matter what you wear skirt, pants, hose, socks, heels, sneakers, whatever just be confident and normal like this is how you always dress and do things how you did them before. If you do that no one will question it. Personally though, I normally go out with friends or my GF so I have support. That other person with me helps me stay calm and confident, but the more I go out the less I need that assistance.

But again be confident and normal, I was talking to a friend of mine cause she had an experience with an obvious TS or TG who would have been fine if she hadn't been so scared, hesitant, and embarrassed. It draws negative attention and brings doubts in the people looking at you.

Hope that helps a little, just know you are not a lone and that you can do it!

[Christie ann]

I have found in my wanderings that at first glance a shorter skirt looks the same as a pair of shorts and the reactions are few. I would definitely go for it. One caveat though, from my experiences, the gas stations and rest stops along the Interstates seem to have a higher "bubba" population than a random gas station/convenience store not on a major highway. Though that could just be a function of my travels in the Intermountain West.

Just do it, enjoy the feeling of wearing a skirt and don't be too surprised at the occasional stare.

[sissystephanie]

My late wife always did my makeup and fixed my wig so I could pass as Stephanie! After she passed away, I just decided to out as a guy in a skirt or dress. Have been doing that for over 5 years now, and have never had any problems! And I do go everywhere, to restaurants, the Post Office, shopping malls, grocery shopping, etc. Sure people do look, sometimes twice! But so what! I dress to please myself, not the rest of the world! I don't expose myself, or dress to look sexual! I dress to look nice. My clothing when I am dressed like that is totally feminine from the skin out. But with an almost bald head and no makeup, there is no question that I am a male! Most people don't care what others wear, as long as they are decent!

[SamanthaS]

Why bother? Your not representing as a man or a woman, but someone in between. If you can't commit to crossdressing all the way, don't half-ass it :(

[annecwesley]

I do it very very often my self and I just dress up completely and really forget that my voice is deep and my face unshaven.

The best advice I can give you is CONFIDENCE!

Do not make it look like you are guilty, scared, or whatever. Act normal do things normal.

That's one of the reasons why I want to do this, to build up my confidence.


Personally though, I normally go out with friends or my GF so I have support. That other person with me helps me stay calm and confident, but the more I go out the less I need that assistance.

But again be confident and normal, I was talking to a friend of mine cause she had an experience with an obvious TS or TG who would have been fine if she hadn't been so scared, hesitant, and embarrassed. It draws negative attention and brings doubts in the people looking at you.

Hope that helps a little, just know you are not a lone and that you can do it

I'm doing this solo. I'm very much in the closet, and my wife would not approve of my dressing out of the house (which I do, but only in the car or private walks in the woods). A long trip away from home is a good chance for me to try it out. I will try to be natural and "normal" - yes, as if I'm not dressed in any way unusually at all.


Why bother? Your not representing as a man or a woman, but someone in between. If you can't commit to crossdressing all the way, don't half-ass it :(

I can't shave off my beard (marital agreement) so I can't represent myself in public as a woman. I want to be out of the house dressed to enjoy the freedom and the feel of my clothing.

[Sallee]

I agree with Samantha, but that is just me.
It sounds like if you want to go our wearing a skirt go for it, have fun.What is the worst that can happen maybe a comment where some one tells you "your wearing a skirt." Your response "Thanks do you like it."
Go for It post a photo it you can

[annecwesley]

I agree with Samantha, but that is just me.
It sounds like if you want to go our wearing a skirt go for it, have fun.What is the worst that can happen maybe a comment where some one tells you "your wearing a skirt." Your response "Thanks do you like it."
Go for It post a photo it you can
I've thought of posting some photos of what I'm considering wearing. I might even show my face.

[Pythos]

Advice?

Well, get cleaned up, assemble a good outfit, take off all your clothing. Slip on your favorite pair of hose, skirt, shirt, and whatever else you want to wear, and head out the door. :)

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.

More men have to get the gumption or courage and just do this. I am very close to wearing a skirted garment to my work. But I need to be sure it is cool to do such (it will be one of my longish skirts though) :)

Samanthas.

I do not consider what I do "half assing" I do however consider your attitude as one of the problems with guys gaining the freedom to wear what they want.

Very polorized view there Samanthas.

[2B Natasha]

Samanthas.

I do not consider what I do "half assing" I do however consider your attitude as one of the problems with guys gaining the freedom to wear what they want.

Very polorized view there Samanthas.

ahmen sister. Who's to say what is and isn't or what one should or can do. Not I. I can tell you that much.

[sterling12]

You might try reading another Current Thread entitled: "Be smart and safe out there." There are huge pitfalls often involved with Partial Dressing.

I didn't say you were doing something stupid, but it's always wise to present well, and not to tempt fate. I have spent a lot of time around Police Officers. They are NEVER amused by someone they think is "pushing their buttons." You do what you want to do, just don't be surprised if there are consequences.

Peace and Love, Joanie

[subwrx]

Some years ago I bought a Utilikilt. ( http://www.utilikilts.com/ ) In the summer I wear it everywhere in guy mode its great I have recived nothing but complements. this year I got some below the knee length outdoor cargo skirts from Colombia. I wear them out doing everyday outings with no problems. I have not gone out in full fem so, this is my cheat it works for me right now.

Dress in whatever way you feal comfortable with.

[annecwesley]

You might try reading another Current Thread entitled: "Be smart and safe out there." There are huge pitfalls often involved with Partial Dressing.

I didn't say you were doing something stupid, but it's always wise to present well, and not to tempt fate. I have spent a lot of time around Police Officers. They are NEVER amused by someone they think is "pushing their buttons." You do what you want to do, just don't be surprised if there are consequences.

Peace and Love, Joanie
I understand using caution by not lurking around public rest rooms in the middle of the night, that seems like suspicious activity in any case. But I've never read a local newspaper report of a man being arrested by the police for having a skirt on. I should think gurls who pass (or think they are passing) are at much greater riskwith the police if they use the ladies room.

When I travel I'll probably use convenience store rest rooms because they are usually single occupancy.

As for partial dressing - I could get fully dressed, head to toe, I have some beautiful dresses - but there's still the beard that would look unfeminine.

[annecwesley]

Some years ago I bought a Utilikilt. ( http://www.utilikilts.com/ ) In the summer I wear it everywhere in guy mode its great I have recived nothing but complements. this year I got some below the knee length outdoor cargo skirts from Colombia. I wear them out doing everyday outings with no problems. I have not gone out in full fem so, this is my cheat it works for me right now.

Dress in whatever way you feal comfortable with.

Well you don't wear pantyhose with a kilt do you? I prefer mid calf length or longer skirts. I have a skirt I wear on my private walks that looks almost masculine - it's long and full, black denim.

[SusieK]

I agree there's nothing half-ass about it, it's just another option that should be available to us.

My only advice would be to take photos of yourself in the outfit(s) that you intend to wear, and then a day or so later look back at them and try to be objective about what you see. I know we're a little biased, but what would you think if you saw yourself out and about?

I totally agree on the guy shoes thing - unless you turn that into part of the look, for example chunky biker boots with a plain skirt, or what about sandals?

[annecwesley]

My only advice would be to take photos of yourself in the outfit(s) that you intend to wear, and then a day or so later look back at them and try to be objective about what you see. I know we're a little biased, but what would you think if you saw yourself out and about?

Thanks, that's the sort of advice I've been looking for. I may take soe photos tomorrow morning in the outfits I'm considering. I may even take them outside standing by my car to get a good sense of how I look in a normal environment.


I totally agree on the guy shoes thing - unless you turn that into part of the look, for example chunky biker boots with a plain skirt, or what about sandals?
Yeah, the shoes have to go with the skirt. And it's getting a little cool for sandles.

[Kelly Greene]

I have gone out in a shirt and skirt, and heels in male mode several times, if I had left out the 4 inch pumps and gone with something more consecrative I doubt that I would have had any reaction at all.
The reactions I have had have been:
Children (teen and preteen) giggling
Adult women saying "he is walking in those heels better that I can" or "well he has nice legs"
I have Been questioned by a mall cop "what's going on SIR" he was wondering what kind of joke I was playing. My answer to him was I am just shopping today.


I have had a rude older teen take multiple pictures of me and a sails girl comment "How rude" to the photographer
I have had a couple of drunks get up set and make rude comments but that what drunks when alcohol is in charge.
these represent the very few reactions I have had when going out in mixed gender clothing, most of the time people are nice and polite the few rude reactions are not in any way the norm but they do happen.

My recommendations for doing this:
if you can, avoid wearing spike heels
be confident ( if you show that you are nervous you will draw attention to your self)
Relax
Smile
walk from the hips
and always remember YOU Belong in this world

[Kathryn Martin]

What about hosiery and shoes? I wouldn't feel dressed without a slip and pantyhose, and my guy shoes are just too chunky for exposed legs.

You have to wear nice shoes like in the picture.

[kymmieLorain]

I was scared the first time I wore ladies jeans. I just knew everyone could tell there were woman's jeans. but the strangest thing happened nobody did. Now That is about all I wear.
I say go for it. the heak with what others think.

Kymmie

[andreana2.0]

subwrx, utilikilts! that is so awesome! i'm just sad that its going to be winter soon.

[sissystephanie]

Yeah, the shoes have to go with the skirt. And it's getting a little cool for sandles.

Anne, if you look at GG's that are out and about you will see that they wear all different kind of shoes. I usually wear low heel shoes and some times even running shoes. It depends on what kind of skirt I am wearing as a guy. If I am wearing a dress as a guy I almost always will wear some low heels. At my age I don't wear high heels, since I don't want to fall! I do some real nice enclosed sandals which I do wear here in Georgia. Of course, we don't usually get real cold winters! The main thing is, dress for yourself not other people! Except for maybe your wife or SO!! I probably spend more time out dressed enfemme, but looking exactly like the guy that I am, than almost anybody else on this forum.As I said in my earlier post, I have been doing it for over 5 years now! And I am out, enfemme, at least part of almost every day!

[annecwesley]

I have gone out in a shirt and skirt... always remember YOU Belong in this world

Thanks Kelly. I plan to dress pretty conservatively. I have a pair of Mary Janes or flats that go well with my preferred skirts, and easy to walk in. I prefer conservative dress, and I figured myself that somehow conservative dress will be less conspicuous.

I'm looking forward to reporting on my new adventure.

[Roberta Marie]

Why bother? Your not representing as a man or a woman, but someone in between. If you can't commit to crossdressing all the way, don't half-ass it :(


Someone in between is what I feel I am, both masculine and feminine. Often, when I'm presenting as either a woman or a man, I feel that I am "half-assing it". Just because you are at one of the spectrum or the other, please don't judge us by your binary standard.

A couple weeks ago my wife & I spent a few days on our boat, and I spent the entire time in either women's shorts and top or a bathing suit, and breast forms. I did not wear any makeup to cover my beard shadow, nor did I have a wig to cover my shoulder length but thinning and receiding hair. I went grocery shopping, into resturaunts, and spent an afternoon on a public beach. I talked to several people in the marina, including a park ranger. I had no problems, but I felt in balance.

[Jason+]

Pick your favorite skirt along with the shoes, hose and other accessories, be ready for looks and questions and go about your business like you belong there.


Why bother? Your not representing as a man or a woman, but someone in between. If you can't commit to crossdressing all the way, don't half-ass it :(

You win, you got me. I didn't actually plug the bass into the amp for the picture. Now let me whole-ass it for you: STOP DRINKING THE PASSING IS THE ONLY WAY KOOL-AID! Did it occur to you that you not everyone has to be a woman to like a skirt?


You might try reading another Current Thread entitled: "Be smart and safe out there." There are huge pitfalls often involved with Partial Dressing.

I didn't say you were doing something stupid, but it's always wise to present well, and not to tempt fate. I have spent a lot of time around Police Officers. They are NEVER amused by someone they think is "pushing their buttons." You do what you want to do, just don't be surprised if there are consequences.

Peace and Love, Joanie

I'm not going to call you a narrow minded BusyGrannyTranny but in the not even remotely humble opinion of this kid it's time to switch to a new flavor of Kool-Aid. Surely with your longevity based wisdom you can see the difference between wearing a skirt during a day time drive and playing musical restrooms in a park after dark that is closed. A wig, falsies and all the makeup in the world would not have kept that individual out of trouble.

[Toni_Lynn]

Some years ago I bought a Utilikilt. In the summer I wear it everywhere in guy mode its great I have recived nothing but complements.

I am going to be going on vacation to be with family for the next 10 days and I will be wearing a kilt every day as I will not be able to CD. I own 5 already, working toward the sixth, and love wearing them when i guy mode. I try specifically not to mixed modes if you will, so apart from undies, it'll be with a guy's shirt and socks.

Never had a bad experience with anyone making shirty comments

Huggles

Toni-Lynn

[annecwesley]

I am going to be going on vacation to be with family for the next 10 days and I will be wearing a kilt every day as I will not be able to CD. I own 5 already, working toward the sixth, and love wearing them when i guy mode. I try specifically not to mixed modes if you will, so apart from undies, it'll be with a guy's shirt and socks.

Never had a bad experience with anyone making shirty comments

Huggles

Toni-Lynn
I've thought about wearing a kilt - for special occasions (Scottish Game events) but I have felt that my shaved legs would look conspicuous.

[kay2]

I frequently wear skirts in public. I typically wear a knee length skirt, pantyhose, and flats or clogs. On top I usually wear a simple shirt. In cool weather, I switch to tights, wear a longer skirt, and add a matching silk scarf. In hot weather I wear a shorter skirt and sandals. No make-up, forms, nor wig; this is my preferred style of dress. I have gone to restaurants, the supermarket, flown, etc... With friends and alone. I have gotten many compliments from women, and sometimes men tell me they wish they had the courage to do the same. I have received a few stares, and more glances. However, overwhelmingly, there is no response at all.

There are caveats here. I feel safer doing this in cities than in small towns. In small towns I have received more stares. I also would not walk alone into a 7-11 at midnight dressed like this. If I am going to be driving in non-urban areas I throw a pair of jeans in the car.

I believe that it would only take a small number of men doing this before it would be considered normal.

As for the one or two rude comments made in this thread, that is extremely rare for this forum. This whole site is based on the premise that society's definitions are inappropriately restrictive.

Best wishes in your exploration.

[Traci Elizabeth]

If you insist on keeping your beard, just put a name tag on reading: "Ringling Brother's Staff" and I promise you no one will say a word to you or think anything about whatever you are wearing! :D

Otherwise, go for it. Just stay safe & be aware of your surroundings and people around you.

[Katrina26cd]

I have worn a skirt in public a few times the problem I have is I have no place to carry anything and I don't like jean skirts

[suchacutie]

ok...what I'm going to suggest you may thing of as a cop out....

If your skirt is a tartan...people will give you a second look...but that's all !

tina

[JiveTurkeyOnRye]

Ok, I don't post on this forum very often anymore but I checked it today and saw this thread and thought it was worth adding into. Anne, I go out as a man in a skirt on a frequent basis, several times a week in fact. I run the spectrum from guy in a kilt to actually wearing women's tops with skirts and tights and boots, and variations inbetween.

The most important thing you need to wear if you do this, is confidence. The first couple of times I went out in public in a skirt, I was scared of what I was doing, so I looked nervous, and intimidated, and because I put off an aura of "I'm doing something wrong" people noticed it and treated me accordingly. The experience was so nervewracking that it took me well over a year to do it again. When I did it again, I really took a good long look at myself in the mirror and said "I really look good like this," and then went out and have never looked back. I keep my head up high, I make eye contact with people, I smile, and I make sure to behave like I belong anywhere I go, and I have not had a single problem yet. Yes, people notice, they might give me an odd look, but then they move on. Occasionally people will make a comment, and I've heard teenagers snicker behind my back, but that's what teenagers do. I've passed loads of cops while walking and haven't been beaten up or even verbally harassed by them at all.

The comment someone else made about really taking a good look at yourself in the mirror is spot-on. The big pitfall of the man in skirt look, when one start to incorporate things like pantyhose and heels especially, is making the clothes work on a male body. I typically don't wear women's tops and dresses because they're usually cut to eccentuate breasts, so for a long time I really had an issue with having this look that seemed half and half, as in top half male bottom half female. The best solution to this is making sure your men's tops are as fitted as possible, a lot of guy clothes are a little too baggy, which doesn't work well with most skirts. But I have had real success with some vintage band t-shirts and skirts with opaque tights. Shoe wise I tend to go with boots instead of heels, I feel like even girlier boots still add a little bit of male-ish weight to the bottom of the look. I've not really had any success with wearing other types of heels in male mode, though I've seen some guys who have.

Also, as a sidenote, I wear kilts with shaved legs all the time and there's never been any issue with that. The kilt or a kilt-like skirt is a good starter-skirt to wear if you're just dipping your toe into the "man in skirt" pond, because it's very masculine and people tend to react to it extremely positively. It's a good way to boost the confidence that you can do more.

Without seeing a picture of you or the proposed outfits I can't really suggest more, so just the generic, but just know that even though I have been doing this pretty frequently for a while now, I still really think long and hard about every outfit combination and really ask myself, does this outfit work well together as a whole? If the answer is yes, I can wear it fearlessly, and do.

For the record, there is nothing "half assed" about how I dress. I work darn hard to look my best and I ask to please be treated with the same respect as any other member of this forum would get, thank you.

[TvRikki]

a couple of weeks ago i went to a petral station with my sister i had no make up or wig on but i was wearing a black arm less top {best i can describe it] fishnet stockings mini skirt and high heels.it was the first time ive been out got a few ppl pointing but i just ignored it and accted as i would dressed in male clothes.Just go for it

[Tima]

I know I'll draw some stares and glances, but I want to do this, and I feel that I can do it with some confidence and simply enjoy the feel of my favorite style of clothing for the day.

Why not? You’re responsible for your own happiness. :)


The second was in Dallas and he was wearing a utilikilt. So if you have a skirt that could sort-of-be a kilt, that would be more believable and may make you more comfortable.

Seeing a "utilikilt" does not mean crossdressing is in progress. It’s a man’s garment, worn by men for reasons of comfort. Kilts are not skirts, either. They are a blatant attempt to project masculinity via “heroic” clothing from a bygone era, but it's actual use is complex. It’s much more fun, and more in keeping with the theme of this forum, to wear a women’s kilt, minus the belt buckles, sporran, and sword pin, and project effeminacy. BTW, I love kilts.

[Kiera79]

meaning I'm not up to that level. I have worn one in tha house and out to the drive thru at mc'ds but thats all, but I sent my mom a picture and my cuz asked her if that was a woman in the pic so I think I'm on tha right track. LOL.

[susan54]

Hello

Jiveturkeyonrye has it sussed. I have been out in a skirt lots of times as man, woman, and everything in between. Obviously there are certain areas to be avoided, but I would avoid thse however I was dressed. It seems you get more adverse comments about being a man in a skirt onthis Forum than you would in public. How ironic.

I have a kilt (I am Scottish). It makes you feel more masculine, not less. And it is not remotely like wearing a woman's skirt. Just look in the mirror before you go out - anything too frilly or lurid will attract comments so just keep it neutral to begin with. Start with a long skirt and a woman's T (perhaps long sleeved) in a plain style, dark semi-opaque or opaque tights and ballet flats. Carrying your money and keys - get a skirt with pockets, or wear a cross-body bag. This means you can be the male in a skirt equivalent of a woman in trousers. You are dressed like a woman but not as one.

I have had more compliments about how I look in skirts (or dresses) than in male clothes. Once you have done it and realise how little reaction you get you will kick yourself for not doing it earlier. The sky stays right where it has always been.

[Rianna Humble]

Why bother? Your not representing as a man or a woman, but someone in between. If you can't commit to crossdressing all the way, don't half-ass it :(

Where is it written that this site only caters to people who are "crossdressing all the way" ?

As I understand it, this site is for all cross-dressers, their friends and families and not just those of whom any individual chooses to approve.

If Anne has an agreement with her spouse that she will not lose the face fungus, why do you want to deny her the right to dress?

If she is comfortable being "a man in a skirt and pantyhose" or even if she is doing this in order to become comfortable like that, then we should do what we can to support her both with words of encouragement and with words of caution. It is Anne's life, we of all people should be able to understand that.

[Lynn Marie]

Why bother? Your not representing as a man or a woman, but someone in between. If you can't commit to crossdressing all the way, don't half-ass it :(

It's bad enough trying to pass when fully dressed and made up. At least most folks aren't sure so they just don't say anything. I won't even get dressed for around the house unless I can get fully dressed and made up. Of course, this has been a rather gradual progression. The thought of going out partially dressed just never crossed my mind. I'm glad it didn't!

[MichelleOhioCD]

Just wear a kilt and talk about the pipes, sporans, skindous and hagus! Sorry if I have murdered the spelling of these Scottish traditions!

[Melissa_Z]

The best solution to this is making sure your men's tops are as fitted as possible, a lot of guy clothes are a little too baggy, which doesn't work well with most skirts. But I have had real success with some vintage band t-shirts and skirts with opaque tights.


Totally agree.

[juno]

Star out with a kilt-like appearance. If it feels good, you can progress to more feminine skirts. Many of us are fairly androgynous, so an gender-intermediate attire makes a lot of sense. However, most people have had trouble "fitting in", so going all male or all female feels better. Others have given up fitting in, and are comfortable wearing whatever they like.

My opinion is that it would look good as long as the style is not too feminine. I wouldn't mix a girly skirt (e.g. with lace and ruffles) and a beard. The important thing is to do whatever is good for yourself. There is no right or wrong. It is just clothes.

[janice murray]

The last thing I want to be is the dreaded "man in a skirt", aaaaaagggghhhh!
I'm from Scotland and nobody bats an eyelid, (except in admiration) at a guy in a kilt.
A lot of men nowadays wear plain kilts instead of tartan usually with boots.
GG's love men in kilts!
Now as to what you wear, ( or don't wear) underneath.
Well that's another story!

[Sandra]

Why bother? Your not representing as a man or a woman, but someone in between. If you can't commit to crossdressing all the way, don't half-ass it :(

Why shouldn't she bother.. just because it doesn't seem to suit you...well hello she has the right to dress as she pleases.

I think you're reply is rude :Angry3:

[annecwesley]

Thanks all for the advice. I'm not too concerened about my top, as it's getting cold and I can wear a jacket. Jackets seem to be naturally more angrogenous, so it's almost more of a matter of finding a skirt that will match the jacket.

I haven't had time yet to take any photos of the outfits I'm considering. If I have time I'll post and ask for opinions.

[JohnH]

If I wear an above the knee denim skirt with a man's shirt and sandals (men's or women's on up to 2.75 inch wedge) people in general do not pay much attention to me. I can even go to an auto parts store in that attire and nobody notices me. On the other hand, If I showed up at the parts store wearing a coat and tie I would be sure to get attention.

[annecwesley]

I'm inclined to wear the long, dark brown skirt. I like the grey skirt with black jacket, but the jacke has gotten a little tight since I took that photo a few years ago.

[Pythos]

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.

[JiveTurkeyOnRye]

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.

[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!

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.

[Sandra]

I like all of them :)

[Rianna Humble]

My vote goes to numbers 1 and 4

[MaryAnn40c]

You could always wear a Kilt....

[SusieK]

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.

[JiveTurkeyOnRye]

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 highly highly recommend picking up a women's style guide. One that I found extremely helpful was this one from Glamour magazine. (http://www.amazon.com/Glamours-Big-Book-Dos-Donts/dp/159240233X/ref=sr_1_3?ie=UTF8&s=books&qid=1287036790&sr=8-3) 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.

[annecwesley]

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

[Rianna Humble]

Good for you! Look forward to reading about it

[Loni]

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.

.

[JiveTurkeyOnRye]

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

[annecwesley]

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.

[JenniferB]

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.

[Sue Too]

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

[annecwesley]

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

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.

[JenniferB]

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 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.

[JohnH]

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.
.

Hmm ... bare legs with a trench coat - that sure looks like a flasher not in action . :):):)

[Nikki101]

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.

[Pythos]

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.

[JohnH]

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

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


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.

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.

[Pythos]

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.

[Pythos]

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.

[JenniferB]

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