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Denim Skirt Day

September 4, 2020


I had a day to get some things done. I did it in a skirt! I wore an above-the-knee denim skirt, purple top, purple mask, beige cardigan, and white sneakers. I felt pretty good about the outfit, but I worried about the colors some.

Gas Station

I drove to a nearby city. I stopped for gas at a place we used to go to when I was a kid. There was something special about this gas station! We always used to beg to go there. It has changed… Over 35 years ago, the man who ran the gas station was always there, and he was always fun. He has moved on, apparently, and now it is just a gas station.

When I arrived, there were a lot of blue collar men wearing work boots stopping in for lunch. I pulled up to a gas pump and got ready. I got out and walked into the building to pre-pay for my gas with cash. I got in line and stayed there several minutes. A truck driver got in line behind me. The ~55 year old woman traveling with him came out of the restroom and walked past me. She was in a bright colored, tight dress and had on reasonable heels. I paid for my gas and stood by my car while I pumped it into my car. Originally, I was unsure if I was willing to get out of my car in this environment. Well, I did get out, and it was a non-event. …but, I strategically avoided as many people as I could… so I cheated.


For lunch, I went to a Mexican restaurant. I ate inside of an actual restaurant for the first time in a looooong time. I kind of feel naughty for doing it. I thought about getting food to-go, but tacos are hard to eat on the go.

I have noticed that people do not notice my denim skirt and white shoes. There is an obvious look that I get when I am in a longer skirt with flats or heels. I did not get those looks very often in this outfit. This skirt and these shoes look enough like shorts and men’s shoes that they are not eye-catching.

I was seated in a booth by the server. Two Hispanic men were seated at a nearby table. One of the men stared at me. I noticed, but I did not care. He seemed lost and distant. He may have been looking past me. Eventually, after five minutes, he stopped. I did not see him tell his companion about me. I looked like he was in a depression. He never talked to his companion. He looked so sad.

I have found that once I am seated at a restaurant, I become somewhat invisible. Maybe a nearby table can see my legs or shoes, but in general, a man in a skirt/dress looks like anyone else while seated at a table. I did notice that a male server glanced at my legs while visiting the two men’s table.

My food arrived. I ate it, paid for it, and prepared to leave. Near the exit, I asked the hostess where the restroom was located. A man who had helped me previously was there and he answered me. I went into the men’s room. No one was in the restroom. I used a stall because it is too awkward to use a urinal when I am dressed like this. Especially when I am wearing so many layers of spandex to control my belly!

While I was in the restroom, several men came and went. When I was ready to come out of the stall, I just came out. I did not wait for the room to clear. I washed my hands at the sinks, beside another man. We did not speak, but we politely gave each other room as is common. He left. I dried my hands. A server was approaching the sinks when I was leaving. We made eye contact and acknowledged each other.

Grocery Store

I went to a grocery store for milk and a candy bar. I saw a woman in a red dress and flat sandals. I made sure to pass her and compliment her. I said, “You look so cute in your red dress!” She replied about doing the best you can with what you have. I walked on. Later, I realized that she may not have seen my outfit.

I got in line to pay. A woman slightly older than me was in front of me in line. I said, “I am going to reach past you to get a candy bar.” I got a Milky Way. She said it was her mother’s favorite. I told her Milky Way candy bars are really good after Mexican food. She talked to me some more. She started talking to the cashier. It took a very long time for her to check out. Eventually, she said, “You are waiting a long time for just a candy bar!” When she finished, I said, “Good-bye to her and she responded.” She knew I was a man in a skirt and she was eager to be friendly with me.

While I was waiting in the line, the lady in the red dress walked up like she was possibly going to get in line behind me. She stood there for a minute. I think she did not realize she had been talking to a man in a skirt earlier. She passed on to do more shopping, I assume.

Hardware Store

I went to a hardware to get an assortment of things. While I was there, several people approached me to help. At one point, a young female employee took me to where something I needed was hidden. A customer in a dress and wedge heels came in and we passed. We smiled at each other. I shopped on an aisle looking for a specific type of washer for 10 minutes while a man shopped nearby. No concern. I found everything I came for and waited in line to check out. The cashier was a pretty young woman. We talked casually. I think that I forgot that I was dressed oddly on this part of my outing.


As I drove on, I came upon a lovely downtown area. When I saw the ice cream parlor, I determined that I needed to stop. I parked my car and went for a walk down the street. It was going to be a long walk to the ice cream parlor. People were eating on the street, but they did not care about me. Some looked. Many never noticed me. No one cared enough to say or do anything. I stopped in a couple stores. Nothing significant happened.

At the ice cream parlor, I talked to the owner for a few minutes. She was happy and friendly and quite chatty. I’m sure she saw my outfit. Christian music was playing in the restaurant. She welcomed me to come back soon. I took my ice cream and went back onto the street.

I stopped in several other stores. I was running short on time, or else I might have tried on some clothes in one store. The shop attendant talked to me for a few minutes and tried to help me shop. She was nice.

Eventually, my large rectangle walk all over downtown brought me back to my car. I got my camera out of my car and walked down to a clothing shop that I had not visited. I shopped around some. An employee started helping me. She was a lovely person. I found a dress that I just had to try on. It fit me so well! The neck line works for me. The pattern is a little crazy for me…. but, I think I would like to go back and buy it. I believe I would want to take in the waist a few centimeters, but it is not necessary. I felt so beautiful in that dress!!

The employee asked me questions about whether I do makeup, etc. I told her that I stay a man and just wear women’s fashions. She complimented me several times. I asked the sales person to take my picture in the dress. The dress is $56. I was not prepared to pay that today. I may go back when I can afford it. Later, I asked the sales person if she would take my picture in my original outfit. She agreed and I asked if she would take my picture on the street. I thanked her and she complimented me again. She said, “I admire you!”

I returned to my car and started driving down the street. I took a right off of main street and I saw to my left a beautifully dressed woman walking up to the intersection. Her dress and shoes were beautiful. Her mask was beautiful, and so was she. I smiled brightly at her and waved as I drove by. What a beautiful day!

I may have encountered 100 people today while I was out and dressed pretty. I am so full right now…. 🙂



From → True Stories

  1. Yes !!! Definitely buy the dress Joey.♥️♥️
    Enjoyed your adventure and I do admire that you get around so much. You are a natural. I am amazed you are not hassled, which is fantastic that you are not.

    • I have never been hassled. I have been openly laughed at once. I have gotten whistled at once (mockingly). I have gotten a small number of hateful looks. I have gotten uncountable looks that told me the person was not comfortable. I have gotten more looks that I would describe as, “Oh, there’s that…” (like “that’s different”). I have gotten looks that pull away so to be polite enough not to stare. I have gotten disinterested looks. I have gotten several smiles. I have infrequently been politely spoken to by someone wanting to make me feel welcome. It’s a Bell curve. … but never hassled. It is like having a lot of tattoos. People may look, but they do nothing more.

  2. Kris permalink

    I agree with Jenny; definitely buy the dress. I love your posts and I’ve followed you for several years. I really admire you!

  3. Christina Cross permalink

    How wonderful to have some say ‘I admire you.” You must have been beaming.

    I also admire you. Your courage to wear skirts openly as you do. I enjoy your adventures and your level of detail. I have followed your blog for about 6 months now.

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