I wore a skirt while traveling on both halves of a trip. It was a very pleasant non-event. On the first half of my trip, when I got to my destination airport, I went to the men's room and changed out of my men's clothes. I put on a long maxi skirt and black hose to hide my 3mm leg hair. I also wore a red top, and long black cardigan. I was surprisingly calm. I was not nearly as nervous as normal. I rented my car in a skirt. I went shopping in a couple stores. I ate at a restaurant. Everything was a non-event.
On my return flight, I changed before going to the airport. I wore the same skirt, and flats. I wore black pantyhose, a black top, and a light men's jacket (with pockets!) I returned the rental car. The woman who inspected the car was cordial. I walked over to the shuttle bus. The driver greeted me politely. A moment later, a woman got on. I said hi. She asked if I was cold. Then we had a conversation all the way to the airport about where we were going, home, etc. It was as if she always sees men in skirts. We got of the shuttle bus together and walked in talking. When we got to an escalator, we both hesitated and then she got on first. I commented, "I think the proper etiquette is for the man to go first. That way he cannot see up the lady's skirt." Then I realized what I had said. I said, "How ironic," because she was wearing pants. We walked along a little more, talking before we separated.
I walked through the airport and through security. A woman in line talked to me briefly. She started by saying, "You look comfortable!" I sat at my gate for a half hour. People looked once or twice and then went on with their lives. I spoke to a young woman who was near me about some heels another girl was wearing. She started talking to me and kept talking to me until we sat in our respective seats.
I ended up sitting by a chatty guy and his fiancée. I walked up in my skirt, so he knew. She came later. I saw her take a few glances at my skirt. I never really considered that she did not know. But she was very friendly. He thanked me for talking to him during the flight. He said he was glad he was by someone he could talk to. At my connecting airport, I felt, for the first time on this trip, that there was some disapproval from the general public. Before, everyone I encountered might have taken an extra look, but they acted like it was rather common seeing a man wearing a skirt. Here, it seemed like people needed to glance sideways and tensed their faces slightly.
I stood in line for fast food and then changed before my final leg for my flight.
It was a very nice experience in the end. I love dressing up. I would love to do it more.