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Thread: What is the worst outfit you wore in public

  1. #1
    Silver Member
    Join Date
    Feb 2009

    What is the worst outfit you wore in public

    Mine was back in the 80s when I decided to go to the mall wearing women's white shorts a blouse and white women's sandals. At the time I didn't have a wig. I have no idea why I went out that way. Today it surprises me that no one hassled me.

  2. #2
    Aspiring Member
    Join Date
    Jan 2007
    Las Vegas Nevada
    The 80s was pretty much a free for all as far as clothes went.

  3. #3
    Member SHINY-J's Avatar
    Join Date
    Jan 2011
    I miss the fashion of the 80s and 90s... women’s clothing was SO much better back then!

  4. #4
    Banned Spammer
    Join Date
    Aug 2008
    Between here and there but mostly here close to the donuts.
    Way too many to mention.
    It took me a long time to figure things out.

  5. #5
    Gold Member Helen_Highwater's Avatar
    Join Date
    Jan 2010
    Midlands UK
    Back in the early days I went out for a night time drive, pre wig days, in a whilte angora sweater that made me look like a cotton wool ball. It was something else "rescued" from the jumble sale bag which is where it should have stayed. Still, learn from your mistakes.

  6. #6
    Join Date
    Dec 2018
    Western North Carolina
    Again from the 80's. Mine was a leotard and tights, in an aerobics class.

  7. #7
    Danielle cdinmd206's Avatar
    Join Date
    Feb 2007
    Southern Maryland
    OMG Jaclyn, I took an aerobics classes just to see the ladies in their leotards and tights. Back then I resembled Grizzly Adams and their was no way i could have worn leotards and tights, but oh how I envied the ladies and what they could wear.

    My worst outfit was probably a skirt and blouse I wore to a soiree n Washington DC that was at a public restaurant. The skirt was a little on the short side but I figured it would be ok. It was until I sat down. The skirt would ride up my thighs and show way too much stocking top, bare thigh and garter straps. I normally will show a bit of stocking top and garter strap, when sitting at the bar in CD friendly places, but this establishment was a straight place and i was way over the top. I ate my meal standing at the bar.

  8. #8
    Junior Member
    Join Date
    Mar 2018
    Liz, this has to be the easiest question ever posed! For a still unknown reason, I thought I looked good in a hot pink wrap dress, white stockings and pumps, a red wig and makeup more suited for clubbing. I took this look to the nearby mall at lunch time in upstate NY. The best I can say is I only got close to the door and lost my nerve, went home and took a good look at myself, something I should've done BEFORE I left.

    PS, I still have the dress and still think I can find somewhere, sometime to wear it.

  9. #9
    Silver Member
    Join Date
    May 2006
    80's for me, too. I used to wear leotards and satin short shorts in drab, but that's not the worst.

    Until I was about 23 or 24 I thought I passed without question. I weighed 125-130, my own hair down the middle of my back. My wife had to work most Saturdays then, and I (with her knowledge) would borrow whatever I wanted from her closet and go do, well, anything just to be out in public. Not to go into the whole story, but I got into a situation where I knew I'd been read and outed to other people who were in this restaurant. It shook me up, and I was determined to not let that happen again. I decided my wife's I decided I needed to wear something that was so overwhelmingly feminine and sexy that there's be no possible way anyone could tell I wasn't female.

    I found an electric blue spandex mini dress and a pair of stilettos that matched very closely. I rolled and teased my hair even bigger than usual. My eyeshadow (and lots of it!) matched my dress, wore the brightest red lipstick and nail polish, and thought I was THE BOMB! I still remember walking into the mall the first time I wore it. EVERYBODY looked. I thought it was because of my powerful hotness! The longer I wore it and the closer the interactions became (store clerks, waitresses, etc.) the more I became aware that this was probably not the secret to passing. I obviously don't know at what percentage I passed, but I got the distinct impression that if passing was the goal, I passed easier wearing the "normal" clothes that I borrowed from my wife. If people didn't read me as a crossdresser, the read me as something. It was still fun to wear. I wore it several times before I cycled out of that look.

  10. #10
    Exploring NEPA now Cheryl T's Avatar
    Join Date
    Feb 2006
    It was probably the night we went to our group meeting.
    I was wearing a nice skirt and blouse. I had on a lacy bra and didn't realize my blouse was as sheer as it was. The only problem was I had added nipples to my forms and they had 1/2" protrusion and large areolas. You could see them clearly, everyone could see them clearly.
    As we sat in the diner after the meeting my wife told me to look in the mirror across from me and as I did she said, "you're such a ****".
    I turned red immediately, but it was a little too late. I suppose she was right about me....LOL.
    Wear what makes you feel Confident !

  11. #11
    Platinum Blonde member Ressie's Avatar
    Join Date
    Feb 2008
    It was my first time dressing in a public place in 2012. I was wearing mostly clothes that were my sister's (RIP) because I thought blending would be best.

    saugatuk outfit.jpg
    "You're the only one to see the changes you take yourself through", Stevie Wonder

  12. #12
    Silver Member
    Join Date
    Feb 2009
    Quote Originally Posted by NjJamie View Post
    Liz, I thought I looked good in a hot pink wrap dress,
    I did something similar when I purchased a verrry short miniskirt in electric pink nylon and thought I would drop mail off late at night. I jumped up on the toll road to return only to realize the automatic toll was out of order. So I pull up to pay the fee and out walks a guy. He looks at me in a sheer nylon blouse with a very pretty lace bra and then sees the pink skirt. I'm sure he thought I was a prostitute.

  13. #13
    Banned Read only
    Join Date
    Feb 2018
    T-shirt, jeans, tennis shoes. No skirt, no boobs, no nothing. Unshaven (On my face as well).
    Last edited by Patience; 09-09-2019 at 02:05 AM. Reason: A lady has a right to change her mind.

  14. #14
    Platinum Member Teresa's Avatar
    Join Date
    Dec 2013
    I'm late replying because I couldn't think of one but then I was going back through my picture section and found the outfit I wore for a St. Patrick's day celebration . OK it was abit of fun and i'd possibly wear it again for a fund raising event . As for the wig , no comment !!

    Last edited by Teresa; 09-09-2019 at 10:21 AM.
    The real me ,no going back.

  15. #15
    Join Date
    Apr 2014
    Wichita Falls , Texas
    Probably the worst I have ever done in
    publis was some years ago I took a large radiator
    To a shop in Plainview , Texas to be
    repaired . I had to wait several days for the repair.
    All the fem things I had were wig makeup
    and several pairs of shorts and fairly long tee shirts
    That's how I spent the week out and about every day !
    Oh how I wished I had packed a nice skirt
    Or two
    It was fun but would not do it again !


  16. #16
    Member Rollermiss's Avatar
    Join Date
    Dec 2017
    other side of the rainbow
    Oooh I love the 80s fashions, especially the high hip V bikinis. For me it was late 90s I went out wearing bright pink short shorts. and a white blouse.


  17. #17
    Senior Member Jean 103's Avatar
    Join Date
    May 2013
    Central Coast, CA
    A friend of mine told me to never wear this again. She said burn it.
    Worst Dressed.jpg

  18. #18
    Senior Member Asew's Avatar
    Join Date
    Jan 2018
    Rochester, NY
    Whatever my mom made me wear for pictures when I was younger. When dressed, possibly an outfit I wore last fall when I wanted to wear some new boots, skirt and cardigan I had just bought and the colors and patterns didn't mesh well, should have made separate outfits for the different items instead. Good thing it is only clothes so who really cares in the end

  19. #19
    Weirdest woman ever! docrobbysherry's Avatar
    Join Date
    Sep 2007
    Orange County, Calif.
    This one! I was leaving a private T event in Vegas and had to pull in and buy gas on the Strip!
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

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