Whats maybe the Craziest/Funnest Outfit you ever put on ?

[Robbiegirl]

So many of us have these bucket lists and I have often wondered if the experience was half as fun as the Fantasy

Did you ever wear a square dance dress, or Playboy bunny outfit, or even harem girl ?

My only really fun one was wearing my sisters new Tennis dress and ruffle but panties. Watching in the mirror how the skirt would swish and fly up while i swung the tennis racket was silly but fun. And of course everytime I barely moved you could see the ruffle butt Panties !

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[Linda E. Woodworth]

Robbie you look GORGIOUS in the included picture.

Where were you playing? Wimbledon?

For the record I'd love to dress up as either a square dancer or playboy bunny.

[Sallee]

I ride bike alot I have only dressed once to ride with riding tights shorts and shirt. No pics sorry. I did for a short ride and felt really self conscious. I certainly could not make that look work as well as all those women who dress in bicycle drag

[docrobbysherry]

Too many ridiculous outfits to just pick one, Robbie. But, have done the Playboy Bunny and harem girl looks!:thumbsup:
These r both very old and horrible quality pics, tho!:doh:

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[Joyce Swindell]

Our Moose lodge had a "Pimp and Ho" dance once. I went as the Ho and my wife was my Pimp. I wore a very short silver sparkling dress with matching 4" heels. She wore a costume leopard print jacket, stick on mustache and dollar sign bling. It was very fun and I would do it again in a heartbeat. I drove and my wife's parents rode along! Too much fun! However...it didn't take long for me to loose the spikes! lol

[Beverley Sims]

I have achieved all three of those things.

I was given the playboy bunny outfit from a TV studio I worked for, yes I had to wear it to a costume party for a bet.

I regularly played tennis years ago in a dress and white ruffle undies and I usee to square dance at one time too.

The funniest outfit was a white rabbit outfit for an Easter Egg hunt.

Which reminds me Easter 'aint that far away. :-)

[LadyStig]

One of my favorite outfits is also super funny because I sure I just look ridiculous. I break out my biggest forms which are just way too big for me. Put on the massive bra I need to hold them. Then I put on some baby pink tights, my thong style leotard, then my underbust corset. I finish it off with my 6 inch “dancer/hooker platform heels.

[Brandie.n]

ballerina,supergirl,hooker and a maid all fun

[Leslie Mary S]

Done the Square Dancer thing several times.
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The yellow 3 piece outfit I picked out when DarkAnGGel wasn't around. She keeps wanting me to burn it fast.
The face makeup was my doing just to be fun. As for the green dress, It isn't. It is just a piece of cloth and I am holding it in place with my hands. We did not take the green outfit out of the studio but I did once wear the yellow outfit once.

PS I still have the yellow suit.

[Princess Chantal]

When my partner and I dressed up as Ukranian Babas at a restaurant for a perogy dinner party with friends. Dressing theme and event was of my creation where all 20+ friends had to at the least wear a babushka. Have been getting asked from those that attended when are we doing it again!

[MarinaTwelve200]

Likely Have to be my GYPSY FORTUNE TELLER----While a bit more elaborate than one I had done several years before, it made me look a lot older and FAT. The eye makeup didn't go as planned either. But it was still "Fun" I just didn't look as good.

[sometimes_miss]

I made a Playboy bunny outfit out of a shiny one piece black bathing suit (snipped the shoulder straps off), rabbit ears, and the bunny tail, collar & cuffs from a real bunny costume. I purchased the bunny cuff links off of ebay.
I have several cute maid's uniforms, again, from ebay.
Cheerleader uniforms, available from real cheer uniform companies.
I have one prom dress from promgirl.com; there are a few decent plus size dresses there.

[RADER]

My Wife once dressed me up in a French Maid's outfit, with Fish Net Hose, and a cute Apron.
I must admit, If it was not for Halloween, I would never wear it and be seen.
Rader

[Nastasha]

A friends Stewardess uniform. With her blessing and help - skirt, blouse, jacket, bra, panties and hose.
We were about a year out of high school and she knew I dressed, I had mentioned more than once how I thought the uniform looked awesome and that it would be fun to wear. So when I said it again one day she just looked at me and said OK, you obviously want to try it on so, if you want to, go ahead and try it on.
It was fun, and just as glam as I thought it would be.

[Ressie]

Nothing too wild. It was an '80s theme support meeting. Asked to dress like an '80s chick rocker.

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[Bobbi46]

I dressed up as a witch for a haloween party. I used a black plastic bin liner as shiny mini skirt. a black tee shirt with the biggest baloons underneath I could find, black licra cycling tights a black pointed hat and broom. I won first prise as well!!!

[Allison Chaynes]

Witch outfit and certain female political figure mask.... went around on Halloween threatening to redistribute candy to kids who were too lazy to trick or treat.

[Joan58]

Allison, Perfect

[ellbee]

Sounds rather boring, but another Halloween witch, here! :wave:


Not really crazy, but actually pretty fun. Definitely memorable, as although I've dressed up quite often for Halloween as various things, this one immediately popped into my head, even though it was like 15 years ago...


And it was all about THE DRESS! :GD:

Though technically, it was a ball gown.

A freakin' *gorgeous* one, at that.


All black, with a stretch velvet long-sleeve bodice, and a HUGE poofy satin floor-length skirt with tons of crinoline underneath.

The weight & volume & sheer bulk of it was pretty amazing & atypical for me. :thumbsup:

Not exactly something you get to wear every day, ya know?


Of course, with the usual accessories, like a femmy witch hat, choker, long fake nails, etc.


Ended up staying home & passing out candy on Halloween. Not a whole lot of trick-or-treaters that evening, but those who did show up seemed to be pretty impressed (and fooled :devil: ).


Was it kinda weird, on some level? Sure, why not. I admit that. Though at the same time, there was no real harm or foul.

Just a fun & different experience for me. And showed that it's okay for adults to join in & play dress-up, too. :p


Oh, and did I mention the gorgeous ball gown?? :yippee:

(Purged long ago, but whatever. The wonderful memories remain! :) )

[abby054]

The most fun? Probably this one that I wore to Oktoberfest 2018 in Portland:

https://www.crossdressers.com/forums/attachment.php?attachmentid=296331&d=1538282601

[Rachael Leigh]

As many have I did the French maid outfit for a party but I also went to a party in what was a pink frilly little girl dress.
More like a toddler little girl

[Asew]

The first outfit I ever wore (and many times after) was a costume for a late 1800s dress with bonnet. It was beckoned me to wear it hanging in the front closet, but definitely something odd to wear indeed.

[Robbiegirl]

Now how did you get lucky enough to have an 1800s dress and bonnet hanging in your front closet ? LOL

For your sake I hope it was something fun like this !

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[michelleddg]

This is Sandy Clifton and me last October at a showing of The Rocky Horror Picture Show at the Wortham Center in Houston. We scarcely turned heads but had a blast. Hugs, Michelle

[Robbiegirl]

Robbie you look GORGIOUS in the included picture.

Where were you playing? Wimbledon?

For the record I'd love to dress up as either a square dancer or playboy bunny.

So Sorry that is the famous female tennis player Chris Everett. I made the mistake of assuming people would recognize her.
I was just trying to give you guys an example of what tennis dresses looked like back in the day
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[Jodie_Lynn]

This would be my craziest outfit. I was "volunteered" as a maid for a fetish party.

[Lana Mae]

No pics! I dressed fully for the first time for a cub scout skit! With my wife's assistance with make up and her clothes, I dressed as a female window washer! (Looked like a bag lady!) The skit is called, The Viper! There is a story that I don't remember but the line is, " I am the viper! I am here to vipe the vindows!" OH, boo! Yeah, I know but it was cub scouts! Hugs Lana Mae

[Michaelasfun]

+1 harem girl. One good thing about cheap Halloween outfits is you have an excuse to buy more next year lol

[BrendaPDX]

I have dressed up as a barmaid outfit and a bride, the wedding dress was incredibly heavy and hot. Sorry no pics.

[abby054]

I have dressed up as a barmaid outfit and a bride, the wedding dress was incredibly heavy and hot. Sorry no pics.

I noticed the same thing when I first tried on my bridal outfit. When that veil came down over my face, it quickly became hot and stuffy under there despite my otherwise bare shoulders and arms. That was unexpected. The veil looks fairly transparent but it really stops normal air circulation.

When I lifted the veil, I felt a rush of cool, fresh air. That must be quite a sensation for a bride in the emotion of the moment as her groom lifts her veil to kiss her. It seems strange that, for all the brides that I have known (and I come from a HUGE family and have been close to many brides), none of them have ever mentioned this, not even those who described everything else in TMI detail.

BYW, only old folks like me remember that that pic of Chris Evert. She is currently age 64. That pic is how she looked in about 1970.

[cdinmd206]

Long story short back in my 20s I dressed as a cheerleader for a dollar ninety eight (yea showing my age) beauty contest for entertainment at a company Christmas party. It took about 3/4 of a bottle of Southern Comfort to get me out on the stage to do my cheer. Myself and another guy tied for first place and the run off was how quick we could put on a pair of pantyhose. I always wore stockings and garterbelt when I dressed so I lost.

[Robbiegirl]

Now that would have been a fun Holiday party to attend !

Did the ladies enjoy watching you struggle to get your panty hose on without running them ?

Are you sure you weren't competing against an other CD ?

[Lynn Sealy]

Long story for context.

Friends had invited me and my wife to a Halloween costume party. Initially, we thought I would go as Ben Franklin. We went to a costume store and I tried on the Ben Franklin outfit. My wife hated it. As we were walking out of the store, she looks up and spies a men’s French Maid outfit and decides we should go as French Maids (no, this is not the most outrageous outfit I have ever worn in public). While publicly hemming and hawing, I was screaming YES inside. She made us go buy matching shoes, wigs, stockings and petticoats. We were one of the hits of the party.

The following spring, my wife told a lesbian couple friends of ours about the party, and how I said if I was going to go in drag I had to do it 100% and not be some guy wearing a women’s costume as a juke. They thought that was great. When we saw them again in the fall, they told my wife “We have something for Lindsey.” It was a 3X latex nun’s costume from Frederick’s of Hollywood. One of them had volunteered at a women’s shelter at which the store had given some overstock items like crotchless panties. The shelter was not amused. My friend asked if she could take the nun’s costume, and the shelter gladly let her take it. After hearing my wife’s story, they decided I would look great in it. They made me try it on for them. Everyone but me laughed. I thought it was great.

A few weeks after they gave me the outfit, we were invited to a Halloween party held by the friends from the previous year. My wife went out and bought a crop to go with the nun outfit. I created a character Sister Margarita Derecho sin Sal (Sister Margarita Straight No Salt) People loved it, many of them kneeling before me saying “Forgive for I have sinned.”

Unfortunately, over time, the outfit disintegrated. Sister Margarita is an ordained minister, and if anyone ever decides to have a costume wedding, I am sure she would happy to officiate.
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[Angie G]

Not very crazy It was just a school girl uniform. :hugs:
Angie

[Nikki A.]

My best was Mimi from the Drew Carey show for a Halloween party at work. Had a picture but I don't know where it went.

[jacques]

hello,
the funniest costume I wore as a skater skirt that fell down around my ankles - my wife laughed a lot!
luv J

[Andrea Chenowith]

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I have a strong attraction to dancers/cheerleaders, and I found this officially licensed Dallas Cowboy Cheerleader replica uniform at a consignment shop.

[Lacy PJs]

... And of course everytime I barely moved you could see the ruffle butt Panties !



Isn't that the purpose of the short skirt in the first place??? :)

Lacy PJs

[cdinmd206]

- - - Updated - - -


Now that would have been a fun Holiday party to attend !

Did the ladies enjoy watching you struggle to get your panty hose on without running them ?

Are you sure you weren't competing against an other CD ?



It was definitely a fun party. Besides me doing my cheer leader thing my wife at the time came out on stage in a men's suit and a gorilla mask and proceeded to do a strip tease. She stripped down to a string bikini which barely contained her big boobs. Needless to say she was a big hit with the men but unfortunately some of higher up's wives did not think so. I deliberately took a long time to put on the pantyhose so I din't win. Didn't want to start any rumors LOL

[Kelly DeWinter]

Defiantly it was this one.
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[ellbee]

Princess Chantal,

michelleddg,

Kelly DeWinter...


That's the way to do it. :thumbsup:

Great job, ladies! :^5:

[Daniella12]

Probably my fancy dress batgirl and Wonder Woman outfits

[HollyGreene]

I volunteer at my local stage school and in the Christmas show, there is usually a comedy number performed by the staff. A couple of years back, they wanted me to join them in a comedy ballet sketch.
During the months beforehand I bought a white leotard, tights, ballet slippers and a tutu in preparation. All proper stuff; not a fancy dress costume.
The comedy sketch was cancelled, but I still have the costume, and I really love wearing it.

[bjsa]

went out to nellis afb dressed as a female dress uniform as a sgt. if they only knew. if played tennis many times tn tennis dress and ruffled panties

[Palaina Nocturnus]

My nickname I was given is Batman lol last Halloween my girlfriend went as Batgirl. A few weeks later I had my own little photo shoot with her costume on :)

[prene]

For me ... I got a wedding gown.

hot and heavy but I loved having the garter belt

[JessicasRabbit]

The funnest for me was recently. I went to a drag show in a rockabilly dress. I got my hair done in a vintage inspired updo, and a GG friend did my makeup.
It was my first trip into the wild. I got plenty of compliments and had a great evening.

[t-girlxsophie]

Nothing I would describe as being way out there,but at Sparkle Transgender weekend a cpl years ago my 2 friends and I ventured out as a hen night party,more Golden Girls than Sugababes but we had a blast,everyone loved it :)

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Sophie

[Micki_Finn]

I’m not usually one for the “costumey” looks but for a mother’s day performance I’ll be playing Christina Crawford from the Mommy Dearest “wire hanger” scene.