I was once taking a piss in my mouth. Long story short I built a shed.

( Dr Preference AjcuiVd289, Fri 1 Nov 2013, 10:04, Reply)

Dressed all in black, on a train to Scotland - black shirt, jacket, troos.
Rather bored, I folded a piece of blank A4 into an inch-wide strip, buttoned my collar and slipped it in, and promptly forgot all about it.

Going to the buffet car half an hour later, however, people's reactions to me changed completely - immediately people were very polite and charming to me, instead of dismissive and rude.

Not so much a fancy dress fail, but fuck it I don't really go in for it anyway, it's Friday, and I don't care.
( Je suis un vagabond is an unfunny, up your own arse middle class knob, Fri 1 Nov 2013, 10:02, 2 replies)

Students
They have a fascinating mindset when it comes to fancy dress. I did a night shift on the door of a freshers party, at the dedicated agricultural campus of a university. They themed the evening as 'Animal fancy dress'.

What pretty much every single female student attending the party thought this meant is 'Dress like a hooker receiving minimum rate from someone with a furry fetish.'

Having said that, how I do some of these shifts without wanking myself into oblivion is a complete mystery to me.
( Muns, Fri 1 Nov 2013, 9:51, Reply)

Last weekend I went to Blackpool on a stag do. I was forced to go to a bar called
Shenanigans. It was the absolute epitome of Blackpool at it's very worst. Lots of people dressed in fancy dress, some had even probably gone to Next and not Primark. There were others in costumes, my favourite party was a group of girls on a hen do. They were dressed as futuristic nurses and by nurses I mean male sexual fantasy nurses , they were all over 60.

It was hell, please go to Shenanigans - fun starts at 9am.

Our stag had the best costume ever to be seen in Blackpool chosen with great care by his best man. A lovely Barbara Woodhouse style tweed jacket and matching skirt and sensible brown brogues finished with a Miss Marple style hat. Pity the over 60's did not choose such a delightful ensemble.

https://www.facebook.com/shenanigansblackpool
( d.r._and_quinch when will you be famous?, Fri 1 Nov 2013, 9:48, Reply)

I went to a lego party dressed as a civet and was asked to leave.

( Zuowan, Fri 1 Nov 2013, 9:45, 4 replies)

I went to a "fancy dress" party in the USA as a clown, only to find that "fancy dress" in the US means "formal dress" and everyone else was in tuxes.
NB: This didn't actually happen, I've never been to America.
( Zuowan, Fri 1 Nov 2013, 9:44, 2 replies)

Me and my mate dressed up as women one year and these guys in the street gave us shit.
Luckily we're super hard cage fighters and we gave them a right pasting.
( Peej, Fri 1 Nov 2013, 9:23, 1 reply)

haha, you dressed up as heisenberg, i never would have thought of that
that is so totally original
( The Doveston haunted by the memory of his own amnesia, Fri 1 Nov 2013, 9:06, 2 replies)

Oh man I totally want someone to come to my funeral dressed as Death that would be well lol

( Je suis un vagabond is an unfunny, up your own arse middle class knob, Fri 1 Nov 2013, 9:03, 3 replies)

once, many moons ago
I went to a fancy dress party as a bath.
Long story short, someone accidently pissed in my mouth.
(plant rolls out of bed like a fat wobbly tub of lard, Fri 1 Nov 2013, 9:01, Reply)

Polyester
I once had a disco outfit. Great suit. Powder blue bell bottoms, tight on the butt: truly awesome! A few years later, and a bit of weight gain too, I decided to wear the disco threads to a ballroom dance convention on a Saturday night at a hotel in Phoenix, Arizona. The outfit was now really tight - not just on the butt, but the crotch too. Every ripple was visible. At the end of the evening, about midnight, I left the hotel and took a stroll on a main thoroughfare. I was taken aback by the reaction on the street. Muscular goons in passing vehicles concluded I was offering teh gay, and were slowing down and shouting threats. Had to make a hasty retreat. Narrowly escaped a gay bashing that night.
(Perv With A Dog had his eyes pecked out by scrub jays on, Fri 1 Nov 2013, 7:34, 9 replies)

Of course, I see fancy dress as a metaphor for cunts.

( d.r._and_quinch when will you be famous?, Fri 1 Nov 2013, 6:19, 3 replies)

Another school chum.
Alby's gonna have fun with this one.

I had a mate, Bruce who I went to school with. He was a smart fellow who despite losing both his parents at a young age was fairly fortunate to have been left a moderately sizeable fortune. There were of course, all sorts of rumours about what exactly had befallen but all Brucey ever told me was "they got in the way of a couple of bullets - teach them to try and stand up to a mugger!"
Bruce always seemed to lean towards the darker side of things - his sense of humour made Ainsley Harriot look positively Michael Jackson-esque.

After school we both ended up at uni and this is where Bruce's proclivity for dressing up and role play came to the fore. He would turn up at pretty much everything in a dark cowl, black cloak and a tight onsey black suit. Suffice to say - all the chicks loved it as he would perch himself somewhere broodingly. TBH tho, due to him owning and running a large multi-national corporation he did tend to have some nice toys to play with. And a pretty fucking sweet ride.
I'd be a liar tho if I didn't say that sometimes playing dressups with Bruce was kinda fun - it got me where I am today.

After uni we headed our own way - I steadily rose thru the ranks of my chosen field after my coming out as a new fresh faced debutante. I was eventually designing for most of the big fashion houses. I found out that Brucey had headed OS to go on sabbatical. China or somewhere. Apparently he made himself a raft of new enemies whilst he was at it.
Me I just worked hard and did all I could to better myself in my work.

A few years later I caught up with Bruce in a rather awkward situation. I'd been at a law enforcement convention peddling my wares and a call came out that a BIG JOB was in progress. The nice deputy commissioner James offered to give me a ride along to see Brucey perform.
Things were uncomfortable to say the least when I caught up with him on the rooftop. He acknowledged me. All I could do was shake my head at his choice in dressup clothing. Especially the cape.

It was a couple of years later that I heard that Brucey had shacked up with a young fella named Dick who was apparently from a travelling circus. Don't get me wrong, I've got nothing against fucking gypos. I just think he could do better.
(s0ckpuppet logging out to reply to you if you're not careful, Fri 1 Nov 2013, 6:11, 19 replies)

I once lived in a shared flat in London with six others
for a birthday we decided to have a Cowboys and Indian party. An irish bloke who lived there we called The Ghost, on account of we never saw him as he worked in the City for an investment bank and would come home at 3 in the morning if at all. For some reason he chose this party as the one to come to, inviting a group of his banker colleagues and his boss all dressed in suits. they were greeted at the door by a short dark brazilian guy with bleached cropped hair. He was wearing gold satin shorts, a sherrifs hat, and no top, and in each hand he had a vibrating dildo gun. The Ghost laughed nervously and assured them it would be ok. Entering the living room they saw a group of women dressed as indians seated on the floor around a esky or car fridge or whatever the fuck you call it in england. It was filled with water and they were doing bucket bongs. As one, they turned around and walked out with the Ghost following them apologising, "honestly I had no idea".
The party was also memorable for two of the cowboys having a fistfight over some long burning grudge which I missed, and an australian guy who we all thought could be gay due to his fondness for michael jackson deciding the best way to come out to his girlfriend was getting caught on the stairs tongue-kissing another guy, which I saw and was hilarious.
( cumquat may will not be commenting further on the allegations, Fri 1 Nov 2013, 0:09, 2 replies)

These aren't the fancy dress failures you are looking for....
Although not strictly speaking the kind of fancy dress you're on about, I find seeing famous people with stupid clothes on equally funny. At least, people dressing up for a fancy dress party have some excuse for looking dumb. These celebrities did it for no other reason that for publicity!

There's this..

metrouk2.files.wordpress.com/2010/09/article-1284451620202-0b290be4000005dc-394102_466x712.jpg

and this...

www.shinystyle.tv/wp-content/gallery/celebrity-bb-2011/pa-11423182.jpg


Oh and don't forget this...
http://www.heatworld.com/images/107286_615x10000_STD/2012/1/kirk_m.jpg
(Om Nom was fed with candy on, Thu 31 Oct 2013, 23:53, Reply)

I dressed up as something about the wrong colour trousers at a first communion or something.
THE BASTARDS.
( Dr Preference AjcuiVd289, Thu 31 Oct 2013, 22:50, 5 replies)

I once dressed up as a shed.

( Amorous Badger NAKED BEA ARTHUR PHOTOS 4U, Thu 31 Oct 2013, 22:40, 4 replies)

I went to a fancy dress party last week
and imagine my horror at being dressed exactly the same as popular b3tan maffers.
What a faux pas!
www.youtube.com/watch?v=de0Eg3UyIcE
( Herb Alpert's Taxi Driver I have very beautiful lips, Thu 31 Oct 2013, 22:27, Reply)

I once wore jogging bottoms to a job Interview
I didn't get the job.

Except I did because it was a job as a Gym Instructor!
(Nitrous Nitrous, Thu 31 Oct 2013, 22:13, 1 reply)

once, many years ago
i was at a party, wearing a fancy dress costume
long story short, I accidentally pissed in my own mouth
( mictoboy shitting in your cunt since, Thu 31 Oct 2013, 21:38, 2 replies)

I once
Was invited to a fancy dress party, me and my little bro were out doing a bit of wheeling and dealing like. We had decided to go as batman and robin. Turned up at the party and the party was actually a fucking funeral! Can you believe it. Our mate Trigger had gone as a chauffeur so weren't the only spastics there.

Later on we found what is called the "lesser" watch and made millions.

True story.
( spanishfly is so fucking sexy people impersonate him, Thu 31 Oct 2013, 20:54, 7 replies)

Fucking hell. You lot complained about Lego, yet now we have this load of steaming turd. You only have yourselves to blame.

( Fucking hell Jeff I am not a robot, Thu 31 Oct 2013, 20:52, 2 replies)

I dressed as...
...a period and then never showed up.
(durtydriscoll, Thu 31 Oct 2013, 20:46, 2 replies)

I once dressed as the Hensel twins.

( drimble he'd been white, he'd been black, Thu 31 Oct 2013, 20:42, Reply)

Maffers once went to a party as a Lego minifig.

( Dr. Shambolic je suis charlie, Thu 31 Oct 2013, 20:40, Reply)

Oh man I went a party once, only to find that what I wore was totally inappropriate.

( Amorous Badger NAKED BEA ARTHUR PHOTOS 4U, Thu 31 Oct 2013, 20:35, 1 reply)

I once went to a James Bond party in a tux with a picture of Sibelius sewn to the back.

( Dr. Shambolic je suis charlie, Thu 31 Oct 2013, 20:32, Reply)

I once dressed as a naturist.

( drimble he'd been white, he'd been black, Thu 31 Oct 2013, 20:26, 2 replies)

Second

( MEATSNAKE Richard Hammond, Thu 31 Oct 2013, 20:25, Reply)

( Dr. Shambolic je suis charlie, Thu 31 Oct 2013, 20:23, Reply)