What would you wear?

Scenario
1) You decided to go to a local crossdressing social group monthly meeting or house party for the first time. You could come dressed from home or are welcome to change at the location
- What would you choose to wear not knowing what to expect others to be wearing?
- Would it be a different style than your preference or usual style?

2) You enjoyed the scenario 1 activity and choose to attend regularly. Taking note that you have become friends and/or comfortable with others and have noticed the diversity of styles displayed are just like on this forum. (Some folks casual, some dressy, some in mini leather skirts, some in more like costumes, etc)
- What would you wear for your second and following get togethers?
- Would you feel comfortable in your preferable/usual style (if you differentiated the style in scenario 1)
- Would an outfit that is rarely ever worn like a fancy ball gown be ever considered as a chosen outfit without there being any specific reason (like the group’s fancy dressing theme) except that you just felt like wearing it?

3) You decide to go to a public event like a dinner theatre where the style of people attending are a 50/50 mix of casual (everyday wear) or dressy (date wear).
- Would you go casual or dressy for the first time crossdressing for it
- Would you dress in the style that is different from your first time for the following outings to the same event?

Since you said "house party", dressy casual should fit the bill. No leather, whips, or handcuffs.

Knowing your dress style, you'll probably look better than most in whatever you wear, anyway.

Patience, I am not asking for advice for me to wear on this thread. I am comfortable in whatever I feel like wearing. I am interested in reading what others would wear.
Btw I have actually worn and seen a few others wearing outfits like a leather corset, mini skirt, studded choker, thigh high boots and etc to a cding house party/meeting with still respecting the group’s rules on behaviour.

It really is true: No good deed goes unpunished.:doh:

Does the event happen in the daytime or in the evening? What's the weather expected to be like on the day of the event? Those things make a difference.

I have been there! The first time I went, I wore a nice dress (below the knee), a little formal but I knew it was an accepting setting. I noted that showing some leg was not an issue, so since then I have worn my gold sweater dress, and a bodycon dress (as seen in my picture posts). I think I blend in with the others well.

I have gone to a club with some of the ladies a couple of times and just dressed to blend with my friends in what I felt good wearing. In a more formal setting, I would probably feel more at ease in something more formal / conservative.

Hiya Patience, I tried to send this in private message but your inbox is full.
I am very sorry if my post came out as punishing, did not mean to. I just did not want the thread to sway into multiple people giving me the similar advise especially when I am not asking. I am really interested in reading what others are comfortable in wearing for the scenarios

No worries, Princess Chantal. I got a forum notification that my inbox was full and cleared some old messages.

Totally get it about keeping the thread focused. It's not unusual for conversations here to go astray or even further.

So, daytime or evening? What's the weather going to be like?

Let’s go with evening as the local group in my city tends to have gatherings starting in the evening (cater to the 9 to 5ers LoL). Indoors as well, in Winterpeg it is common for us to wear jeans or pants in the winter to the establishment then take them off if wearing a dress or skirt. Also it is common for us to bring along heels in a carry along bag to wear indoors (even if not cold outside)

Geena,
My first time to a monthly meeting I went in total guy mode and took notice how others dressed so diverse. Helped me in deciding what to wear for my first meeting crossdressed. Went with a red velvet mini skirt, black top, and ankle boots for that meeting then with becoming a regular I just went what I felt like wearing whether casual, dressy, clubbing, costume, etc. was just a comfortable place to play with styles

Good to know.

Well, it's not a beauty pageant and in all likelihood there will be some variance in each individual's crossdressing abilities, so not being the kind of person that likes to draw attention to themselves, I'd probably wear a black top and a patterned skirt (or vice versa), stockings, comfortable shoes and a light jacket.

I also have some animal print tops I like to combine with black pants and skirts. Seeing as it's a crossdresser meeting, I'd do everything I could to avoid having to wear trousers.

If I opted for a dress, again probably black or some subdued color. That's what I would wear for a house party if I did not know anybody there.

I'd go with a little black dress, something sexy but not trashy, med. heels. For all three .

Hello Princess Chantal,

1) I would keep it simple, skirt just below my knees, blouse, lighter color than my skirt or white, low heels or flats.
2) Probably a nice sleeveless spaghetti strap dress, hose and strappy heels. Or possibly a knit top 3/4 sleeves, skirt a little darker than the top, hose, and a bracelet or two.
3) Definitely dressy.

Brenda

If I was to go to a crossdressing club the first time I?d dress in black as in black dr marten boots and thick black tights with short pleated skirt and black top but no makeup.

If I got approval and I attended again I?d wear high stilettos and black ultra sheer pantyhose and dress with make up red lipstick and brunette bobbed wig with fringe.

If I got invited to a dinner or public event I?d change the pantyhose for black lacy garter belt and sheer black stockings under long dress.

I've never dressed in front of anybody, but, if I ever did go to a crossdressing meeting, I'd try to look my best, so I'd dress to the nines, little black dress, high stilettos, full make-up and long brunette wig. Personally, regardless of circumstances I'd try to keep to a feminine style, so skirts, dresses, full make-up and heels all the way, I'd avoid trousers and flat shoes.

For me, I would dress a little nicer than expected. It is always better to be a little overdressed than underdressed.

I can give an example. 20 years ago I got invited by a friend to join him in visiting one of his old friends. That person was a Lawyer with a big firm with an office in Washington, DC.
I flew in Friday night, got picked up at the airport. Casual night a few drinks before bed. Next day since both men were bachelors and cannot boil an egg, I decided to cook one hell of a meal for them Saturday Night.

Sunday we all got invited to a Easter Dinner at someone's home in Georgetown. The family owned a manufacturing company in Virginia and was rather well off financially. The husband was in his 60's and the second wife was kind of a Trophy if you know what I mean. Around the table was quite a mix of people. One woman was a news producer for ABC news, another person worked at the Capital doing what they do at one of the desks you see people sitting at when you watch C Span. A few more DC connected folks where there.

Anyway, long story was I did not have the proper attire, golf shirt and slacks, for a dinner like that and I felt uncomfortable all afternoon. So, overdress if you have the means to do so.

I had to think about this for a bit. I probably would go in what might be business casual. In my minds eye I was thinking of a black eyelash sweater with a v-neckline, paired with a gray knit pencil skirt and black pumps. Ive worn the same sweater with grey wool slacks.

If it was a public event, I guess the venue and season would guide the choice. Again, I am imagining an event in an nice restaurant, and since its still chilly, I would go with a wine colored rib knit mock turtleneck, paired with one of my favorite skirts?a textured pencil skirt woven of black, red and silver threads?undecided on wine or back tights and red heels.

On a special occassion, I might pull out a gold sequins party dress that I bought for a Dancing with the Stars party last year. Then I would be vacuuming sequins from my carpet and car for the next six months.

1) I think I'd wear something casual like jeans, a tunic top, tennis shoes, bra (w/forms), wig, makeup, jewelry, and nails.

2) If I were to return regularly, I would prefer wearing a party dress with nylons, dressier shoes, and the rest of the "equipment."

3) I'd prefer to go dressed as mentioned in item 2 above.

My answer is a lot smarter now than the first time around when this actually happened to me. I'll tell you what I did where and what I would wear today . 20 years ago I went to a local support group meeting at a private house. I did not dress and immediately upon arrival wished I had. Everyone was so friendly the looks varied from "I just fell out of the dryer" looking all disheveled to some who were more perfectly put together. Nowadays I tell someone to wear whatever you want. Just about anything goes at an event like that. You might reconsider if the event is public but it's still kind of like Halloween dressing up. No one will care how good or bad or out of place your look might be.
I think the next few times I went to that event I wore a short skirt hose and very high heels and a blouse. something that might have looked appropriate as business attire. Nowadays I'd probably be a bit more casual maybe even a dress but nothing too fancy. A big gown would probably be awkward and get in the way depending on where we are but otherwise at that house party it wouldn't matter. people would probably love it.
As for going out with the group I'd probably wear a dress and I actually have with that same group early on so not much change there. maybe pick something a little more tasteful these days and More in line with what women going to that same location might wear.

If you don't know what others will be wearing choose something in a classic style.

Its smart enough to fit most situations

Unless there was a weather issue I would choose, blouse, knee lenght skirt with 3 inch heels.

I would dress as a normal, "real" woman my age would dress for the occasion. No mini skirts, no exaggerated makeup and no hooker heels.

1) I would dress at home just like I always did when attending support group meetings.
I would wear whatever felt right that night. I can never pre-plan things like that as that day I might have chosen a skirt and blouse but end up feeling like it's a skinny jeans and tunic night. I just go with my feelings that day
unless there is a theme.
2) The answer would be the same. It's what I feel like that day.
As for a fancy ball gown. No, not for a meeting. Unless again there is a theme and that's what everyone is wearing.
3) Dinner theater? I would dress it up for sure. Not ball gown style, but definitely a pretty dress, hose and heels.
For followup events of the same type/same venue I might dress it up more or tone it down depending on what the theme is. Were it something like Phantom of the Opera night I would surely wear a ball gown. Were it
Murder in the Rue Morgue then I might do leather pants with a corset top and maybe slight goth makeup.

Everything depends on my emotions and the venue/event. I prefer to let them dictate my outfit and not pre-select anything.

I?ve never been to a cross dressing social group but if I did I would probably go smart and not to over the top makeup !! I?m not really a fan of casual.

Chantel,

When I am out by myself or just running errands around town, I dress nice casual and sometimes sexy casual. But opportunities to get really dressed up are much less frequent and when they do come along I always jump to take advantage of them. I feel the most feminine when I am really dressed to the nines. In all 3 of your scenarios, I would dress up as nice as possible without wondering what everyone else would wear.

I belong to a CD meetup group that hosts private dinners every week at their apartment with 10-15 ladies usually attending. Most gals wear nice casual clothes or skirts, a few wear basic dresses and 3 or 4 always get dolled up. I am in the last group and always wear a cocktail or evening dress and it is heavenly. It is very difficult to get undressed at the end of the night.

Fiona

A CD party? I'd probably dress as trailer trash. Fishnets with heels, Daisy Dukes, cami with bra and boobs. No makeup, but I'd shave and let my hair down.

So it's probably a good thing I've never been invited to such a thing. :)

A public outing? I'd likely go much more conservative, maybe colorful leggings and a cute t-shirt, maybe an unstuffed bra.

I would wear a decent skirt and top or an evening dress and little bling.

My 1st time was like you in total guy mode about 35 yrs ago. I was sorry that I didnt bring more glamorous outfits like everyone else.

Chantal,

This is another of those posts that takes me back to my earlier days my first interaction with others of our community at a support group meeting. I can't remember if I wore a patterned crossover dress of skirt and blouse combo but I do remember wearing a pair of strappy white kitten heeled sandals that weren't the most comfortable as if memory serves they were a size too small.

Subsequent visits I stuck with smart casual and definitely more comfortable shoes, still heeled of course.

Going to the theatre is on my bucket list and were it to be a play or music performance then again smart would be the order of the day. I would love the opportunity to go to a gala performance and put on a few more sequins, something full length and figure hugging. Just need a years notice (at least) to get more weight off.

Well, if any of those things were happening right now I have pretty much one look. Black leggings, an oversize sweater, and either modest heels, ballet flats, or mules. I can dress it up a little by my choice of tops and shoes, but other than one sparkly sweater I don't have anything dressy. I'm quite boring these days. Now, it it was 10 years ago, or 20 or 30 or even 40(!) my answer would certainly be different.

A great set of questions. Obviously the answers will depend a good bit on where we all are (maturity, physical location, acceptance in the community, etc) in the overall scheme of things. I recently went though this process, having attended my first group meeting in September.

1. The group meeting I attended was in a function hall and was the first time Jennifer had ever been out of the house. I had been dressing for quite some time and have a tolerant wife so I was comfortable in the clothes. Before the meeting I enquired as to what to wear. The answers I go were basically "whatever you find comfortable". So, helpful, but not really when it comes down to looking in the closet. :)

I consulted with a GG friend and shared some pictures in various outfits. She liked many of them, and nominated a few. But again the response was basically "go with what is comfortable". So, ultimately I went with a leopard print a-line skirt and a black chiffon-type top. Added some platform wedges in a nude color and a black bag. I think the outfit worked well on me and was not at all out of place at the meeting.

2) So I did decide to continue going to the group's meetings. The next meeting was themed Halloween since it was in October. I thought about doing a real costume. But ultimately I just settled on a halloween themed tunic top over black leggings. Added a different bag and black flats for this one. Fun time. Some of the group came in full costume mode (maid, 50's housewife, hula girl) and some in just ordinary female clothing.

3) The next group event as a girls night out at a local restaurant which is attached to a large mall. Another big step for Jennifer as the previous two meetings were in a safe, controlled environment. Now Jennifer would be very much out in public. I decided to go fairly christmas dressy with a bright red top, pleated black skirt, black hose and black flats. Was going to wear heels but was afraid of the distances I might have to walk in them as well as the fact that I'm not adept at them.

So overall, I stuck to my comfort zone and basic casual/blendy style.

We have another meeting coming up next week and it looks to be a GNO at a restaurant yet to be decided. I'm totally up in the air about what to wear but that will somewhat depend on the actual venue. I suspect though that I'll stick with my same style.

As one who has only underdressed in the big wide open this is on the bucket list someday. If I were to do it Im sure there would be a lot of communication so Id feel comfortable. The first meeting would probably be business casual either dark womens slacks with a white blouse and nice pumps. It?s chilly so maybe a feminine coat and of course jewelry. Or I could replace the slacks with a nice skirt.
On future meetings it would depend on the theme and the weather. I could wear jeans shorts or LBD.

In all of those situations, personally I would wear a skirt suit, or a professional looking dress and a blazer. In my experience, this look tends to always goes over well with people. It is dressy and formal, with a skirt, stockings and heels, without drawing too much (or negative) attention. I also found people in the general public tend to be a bit nicer to me if I look like a professional woman, even if I am technically overdressed and/or they read me.

1. My first group meeting was for Halloween so I bought a Dorothy costume (Wizard of Oz), so that was a special case.

2. For my choices to subsequent meetings, I didn't consider what the others wore. That doesn't really matter to me. I shop for things that I think look good on me. When I shop I always ask myself "would I wear this out?" and the answer is generally yes (and if I really like it I take my GG friend Renee's advice to buy it and find a place to wear it). Renee has also encouraged me to expand my comfort zones, and I have.

3. Absolutely, positively dressy. I bought a great dress and needed a place to wear it, so I bought a Hamilton ticket and wore it to that. My second play was Hairspray with another GG friend so I wore a pink dress I like. I've gone to three rock concerts and try to dress in rock babe style. The third concert was definitely more aggressive than the first two.

This is a fun thread with lots of interesting responses. I’d split the difference in these circumstances. I like the contrast of a a casual outfit with something a little sexy. Maybe jeans and a blazer over a lacey top? Add a choker, fishnets and heels if you feel like slicing it up a bit??

I think I'd go dressy casual, but I'd have my beard and ponytail. I am, and present as, a feminine styled male rather than female so I am not sure if I'd even fit in at a function like that.

A mid thigh mini dress and stilettos. And block heels to get to get to the party before changing shoes.

Marion

Thanks for all the good reads folks! I loved all that was shared of your outfit presentations (possible choices and for some past choices). I am sure that the reading of the thread may help with someone picking out an outfit if they choose to do one of the scenarios in the future