Friday, October 29, 2021

Swingin’ ’60’s Chick

In honor of our favorite holiday on Sunday, I am reposting past Halloween posts every Friday in October. The following is a repost from my old blog, dated October 2006.

Saturday was fabulous!

My makeup went on flawlessly. I think that after 40 years, I am starting to get the hang of it! I was trying to achieve that big eye look that was popular back in the late 1960’s and I think I did a good job of replicating it. False eyelashes were the key to achieving the look. I was very happy with the results.

Darn fishnets started tearing as soon as I pulled them up over my fanny, but the tear was in the crotch and did not spread, so I left well enough alone. After I put on the dress and the boots, I looked just like another swingin’ chick of the ’60’s!

I was ready to go at 5:30 PM, which was much too early for heading out to my support group’s meeting/party, so I decided to visit my friends Patty and Ron and let them see my costume. I called to make sure they would be home (they would) and then I hit the road.

I wanted to stop and buy some pastry for the party. I remembered that the local IGA’s have nice pastry, so I stopped at the IGA in Southington to shop for the sweets. Note well that with my go-go boots, I am about 6 feet 5 inches tall and dressed unlike anyone else in the store. I walked to the extreme opposite corner of the store where the bakery was located and I did not notice anyone noticing me, neither customers or store staff.

I picked up some strawberry and cheese mini-Danishes and proceeded to the cashier. There were two lines, each with about 4 or 5 customers. As is my way, I managed to choose the slow line and was stuck right behind an elderly couple who were taking their sweet time unloading their shopping cart.

A 30-something woman in the other line noticed me and smiled while checking me out intently. I don’t know if she was smiling because she liked my costume or because she realized I was male. I was hoping that we would leave the store at the same time and that she might say something, but with Ma and Pa taking their sweet time in front of me, she was long gone by the time I checked out.

As Ma was removing the last item from her carriage, she noticed me, gave me the once over, then turned to the business at hand, i.e., paying the cashier.

I was next. The male cashier asked, “How I was doing this evening?” and showed no signs that he knew I was crossdressed. I paid for the pastry and exited the store truly amazed at how anti-climatic it all had been.

I visited Patty and Ron and met their two bijon frise dogs. Everyone including the dogs, seemed to like my costume.

Then, I headed up to West Hartford for the party. There was a nice crowd... about 15 to 20 people, most in costume. It seemed that almost everyone brought some goodies to eat. It was quite a sweet spread!

I received a number of compliments for my costume and makeup. That was nice!

I guess most everyone had a good time because the meeting/party did not break up until after 11 PM, which is the latest I have ever seen a support group meeting break up.

Source: New York & Company
Wearing New York & Company

Couple crossdressed for Halloween
Couple crossdressed for Halloween


  1. That's Mary Quant gear! I wore it a few times myself.

  2. As a season ticket holder for Maryland Volleyball and basketball I see women in the 6'5" height regularly. Be tall and proud, Hon' Just look at RuPaul -- in her sky-high heels and wigs, she's over 7'! Before my foot troubles I used to be about 6'5 in my 4 inch heels, and I was not nearly the tallest lady at my group.