As a crossdresser...

[CarlaWestin]

What is the craziest or most elaborate outfit or ensemble you've ever worn?
Go ahead and answer while I try to figure out what mine is.

[RADER]

On two occasions, both where on Halloween's, My wife dressed me up as a French Maid;
Complete with fish net hose, and white apron. I had no wig's at the time, so I went bald
as an Eagle, handing out candy to the "Trick & Treat'rs"
I had a ball, lot of fun, and many complements on my "Costume" for the evening;
specially from the "MOM's"
Rader

[Rachael Leigh]

That's easy I wore a pink frilly little girls dress that included diapers.
Went to a party like this too

[Nikki A.]

Mine was Mimi from the Drew Carey Show for Halloween. Loud red floral dress, hose, red shoes and of course Blue eye shadow. I did it for work, and for a party the next night. Big hit both times.
I did dress very classy for a wedding, nice beaded pink dress. It was a wican, lesbian wedding and I did have the brides full support.

[windycissy]

Square dancing with a huge flouncy petticoat under my skirt, so much fun to twirl around in :)

[AllieSF]

Halloween costumes, as in, "What the hell was I thinking??!!"

[Dana44]

Well last Halloween, Day of the dead dress. skeleton hose, read and black hair wig. And zombie type makeup. A sexy zombie babe.

[Teresa]

Carla,
I have a couple of French maid outfits , one in black satin and the other in black PVC. I also had a PVC nurses outfit. I have worn a couple of wedding dresses.
Maybe the craziest moment was when I tried on a PVC dress in a sex shop and had to ask the male SA to zip me up.

Now I'm out socially I may try to be more sensible but there is a Halloween theme night planned so who knows. Photos may appear !!

[windycissy]

Halloween costumes, as in, "What the hell was I thinking??!!"

Allie, the red wig is a tragedy but the serving wench costume is adorable and the tigress too :)

[Sometimes Steffi]

Let's see

French Maid (on Halloween), the old switcheroo (my wife was the butler)
Hooter's girl on Halloween, and yes, I went to Hooter's that night
Wedding gown for a photo session with Amanda
Strapless vintage/ethnic red/gold iridescent gown with a matching shawl (to the Keystone Gala)
Several different renaissance dresses (to the Maryland Renaissance festival)

I went out in all of those (except the wedding dress). I'm afraid to tell you what I wore in the privacy of my own home.

[nikkiwindsor]

On Halloween back in October 2014, I went clubbing at several bars wearing my dirndl costume! I should connect with Allie and go to a Renaissance Festival with her...I think we'd be cute together!

[TrishaTX]

on of the first time I got a full make over I was about 40...but looked like 60!

[sometimes_miss]

Easy. My avatar outfits. I try to duplicate the look as best I can, as well as the girl underwear, make up, nail polish, the whole nine yards. I was lucky enough to get the boots and shoes before they stopped making them in my sasquatch foot size. The dresses are available at birchplaceshop.com as well as a couple of china vendors on fleabay, in custom sizes including my six foot four, 260 pound frame.263829

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[StacyCD]

Princess Leia is mine. Sorry no pics!

[Brenda Freeman]

I love petticoats and lace dresses, so I have a french maid out fit and some square dancing dresses that are fun, and of course a wedding dress just because.

[BrendaPDX]

Hi Carla, A wedding dress complete with a crinoline A-line petticoat, white corset with hoes, bra with forms, white panties, white satin strappy 4” sandals, wig, and veil. I was surprised at how long it took to put on, and how hard it was to take off.

[Lily Catherine]

Over:
Ball gown bought from wedding boutique for cheap
Long black wig
Spectacles (obviously)

Under:
Strapless bra with matching thong
Black pettipants
Extra full petticoat
Stockings
Pumps

I felt exceedingly beautiful in it even though it was a colossal hassle moving around. I'd like to get back in one of those, maybe with an extremely full hoop skirt and a boned corset. Also, proper forms and a cleavage-revealing neckline.

[CarlaWestin]

I looked through a couple of thousand images and the ones that I hadn't really gotten into makeup or wigs and I still wore glasses, were strong contenders.
But, then I found this shot. I was getting artsy and really starting into the theme dressing.

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[Pat]

My looniest outfit was from a few years ago when I was a magician's assistant in a show Provincetown, MA. I had eyelashes that were so heavy I could barely keep my eyelids up and my "earrings" were dream-catchers we found in one of the local shops. Very supportive audience and it's a gig I look forward to every year. (Happy to say I've lost weight since then. ;) )

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[Allison2006]

Mine would have to be when I went out on Halloween a few years ago wearing a school girls' costume.

[Samantha54]

Went to A Halloween Party dressed as Dorothy from The Wizard of Oz. I actually had one GG ask me if I was a girl. I guess I looked that good!

[TillyM]

Here are a couple of my best outfits!

[CarlaWestin]

Cute! From bunny to nunny!

[AllieBellema]

Would probably have to say my Belle cosplay since I have to wear two hoop skirts underneath to hold the skirt up. Does make the dress feel a bit heavy to move in, but still looks good afterwards. Also just tried the same with my wedding dress and made it look good.

As matter of fact, I think just about all the things I wear get a bit elaborate!

[Cara Lacey]

On Halloween I usually dress as Elvira.

[Teresa]

Carla, Sorry I forgot to attach an image with my reply , I know you've seen it before but it was still fun .

[CarlaWestin]

Oh, Teresa. Those are great. I love it when we just want to have a little fun. This morning, I was a sissy, out putting gas in the car.

Outrageous!!

:straightface:

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[Angie G]

My school girl outfit with ruffled socks And plad mini skirt.:hugs:
Angie

[5150 Girl]

Either Elvira Mistress of the Dark, or Wonder Woman. Then again, I also had a lot of work in my I Dream of Jeannie costume, and Carrol Petelli from Walking dead to...

[mikayla1964]

264948264949 last year working a holloween festival as a fortune teller

[TrishaTX]

wow there are some great ones on here...I think maid outfit is probably the craziest I wore out. I tend to stick with regular female dresses..

[Jill999]

Amazing pics and outfits.