The clothing you were least comfortable wearing outside?

[kimmy p]

My Halloween plans are already in motion. I pushing my comfort level all the way across the board this year by dressing as the classic French Maid. Complete with corset, stockings, garter straps, and rhumba panties. Too tell you the truth this is almost past my limit, and I'm a bit nervous. I love the costume, and have been drooling over it for months, but trying to fit in will be impossible, and I'm a bit nervous. What outfits have you ladies worn that might have pushed your comfort limits?

[TabbyJames]

Pushing it is hard, for me it was shorts so short that even the best gaaf wouldn't work, coupled with 6 inch heels on a 6 foot frame and a short cut halter on 210 lbs. I am sure I looked freakishly horible but had fun doing it.....

[Tiffany8]

My birthday suit.

[Paula W]

Super short skirt on a windy day.

[sissystephanie]

I guess the one that really messed up my comfort level was my "short" black leather mini skirt. I had it on one day when I stopped to fill the gas tank. As I was standing there, completely exposed, the snap holding the skirt suddenly broke. The skirt fell completely to the ground, leaving me standing wearing a pair of bright red lace panties! BTW, I never tuck, so there was no question about my sex! I shut the pump off, pulled up my skirt and got out of the station as fast as I could.

[Rita D]

Once went as Elizabeth Taylor In "Butterfield 8" to a movie theme party wearing a white slip and a mink coat (she is dressed this way in the film). It was exhilarating AND nerve -wracking all at the same time- But I came in 3rd in the costume contest!

[Taylor186]

Unless I was out as a CD to everyone I know, and I mean everyone, I wouldn't wear a nice normal dress & accessories--the kind that you might find at any major department store.

[JoanAz]

As in my Avatar and Photosection, I love SHORT....By the way I am 6ft 230# and 70 years young,,Just go for it
OH YEAH! all my heels are 5 inch...

[erickka]

A SHORT (10"long) mini skirt, 8" platform strech knee boots and boobs so big I needed a sky hook to hold them up! Yep, you guessed it, I was a Hooker Babe extreme! I surely got a lot of stares that night.

[lilmissjenny]

last halloween i wore a Playboy catholic school girl outfit that BARELY went past my stuff. after awhile of wearing (and being cold), i put some jeans under the skirt...lol.

[Midnight Skye]

This is going to sound really stupid. But going out enfem, I'm least comfortable in Jeans. I can go out in a denim mini skirt... but in denim jeans I constantly feel like my third leg is going to jump out and bite someone. Not surprising I pass better in jeans despite being un-comfortable

[DonnaT]

I've worn my maids outfit to the club for halloween, and felt comfortable in it.

I guess I'd feel the least comfortable out in public in (besides the maids outfit) any of my micro skirts.

[kimdl93]

Outside as in public - nothing more than rather androgynous women's tops/slacks and sandals. I really try to be discrete and blend in rather than shock anyone.

[kayegirl]

The tight leather micro mini skirt, that made me feel like one of my dear Mum's expressions "Mutton dressed as lamb". Only wore it the once and it went straight to the charity shop.

[Veronica Lacey]

While I would not jump to wear a dress out and about I must say that I feel most uncomfortable wearing a male suit and tie. I just don't feel good about wearing one and this generates similar feelings of insecurity when I have to (weddings and funerals only.)
Go figure?

[Cristi]

I have a favorite skirt... about knee length, soft and very light material. I love it. *BUT* it is not something to wear on a day with any wind at all. It likes to 'float' UP with the slightest breeze.

So probably the most uncomfortable I've been out because of what I've been wearing was when I was taking a nice stroll downtown in that skirt (before I knew that it could be trouble), nude pantyhose and heels when suddenly the wind kicked up. The buildings I was walking between started funneling the wind and before I knew it I had a full-time job with my one free hand trying to keep my skirt down (the other hand was holding a cup of coffee and my purse).

I'd push the skirt down in the front, and it would fly up in the back. As soon as I got it down in the back, the side or front would be up at waist level again... I don't know HOW many people I unintentionally flashed as I rushed back to the car!

Yes, there can be a bit of a thrill when a random wind lifts your skirt, but it is no fun at all when it just never stops and you can feel the eyes of every pedestrian and driver on you (at least it FEELS like they were all staring at me)!

I still love that skirt, but only wear it out now after carefully checking the weather and wind predictions.