Since I’ve started wearing skirts, I’ve come up with a number of ways to build confidence in wearing them and other gender-non-conforming clothes out in public. One of the ideas I had a while ago, was to plan a multi-day trip to another city but with a twist: I would only bring skirts.
This is an idea I’ve entertained for a while now. Essentially, the plan is to take my family on vacation for several days to another city and leave all my bifurcated lower body garments at home. I’m going to travel there in a skirt, regardless of whether by car or train, and then once I’m there, I won’t have a choice but to wear skirts out in public unless I want to hide in my hotel room for the entire trip.
While I thoroughly enjoy wearing skirts out in public and do so on a regular basis, it still costs me a lot of energy to get over that initial hesitation before leaving the safe space of my home. That means, I usually have less energy for whatever I am going out to do simply because of this nonsensical hurdle in my own head.
The hope is that going to another city for several days with only skirts will force me to practice getting over this hesitation so that it doesn’t cost me any energy at all anymore. Once I’m out, I don’t have a problem anymore and enjoy the experience. The best way to get over a fear is to face it and this would force me to face it much more frequently and thoroughly than when I am at home and don’t have to leave the house every day.
The other factor that plays into it is anonymity. At home, I’m not really worried about my neighbors and what they think because they’ve all seen me wearing skirts already anyway, but there is still comfort in the total anonymity you get when you are in another city where no one knows you. The likelihood of you seeing someone twice in a large city that you don’t frequent is very small.
In any case though, I decided to write about my idea so that it might help others. Maybe some of you who are struggling to find the confidence to go out in public in gender-non-conforming clothing will find it helpful. If you do, definitely let me know how it went! I would love to hear about it!
As far as my own plans go, I will write another post about it here once I’ve done it. We don’t have any concrete vacation plans yet, but I’m sure we will later in the year. I will write about how it went and what my experiences were. Hopefully, I’ll even have some photos to share. I’m optimistic about it and am even looking forward to it.
I did something similar in Las Vegas, except my gender-non-conforming clothing of choice was over-the-knee boots. It was early on in my exploration and was a huge confidence boost.
Some friends were going to a concert there so I flew up from San Diego to hang out. After I picked up the rental car, I switched to boots and wore them at every opportunity. I can remember my heart racing as I put them on, thinking am I really going to do this? In situations like this, I try to remember the best advice I got as a guy wearing heels. “If you are having fun and enjoying yourself, others around you sense that and are cool. If you are nervous and slinking around then they would be nervous too ”
My first obstacle was parking. I switched parking lot and parked at a higher level just to minimize the distance I had to walk. My second obstacle was the flooring in the hotel. It would alternate between carpet and marble. I had to constantly adjust my stride so I wouldn’t wipe out. One friend loved my revelations. These are normal thoughts for women, but I’m discovering them now. It was similar to my shock that skirts don’t have pockets! My third obstacle was the hardest one – standing in line to check in. What will people say? It was busy, and at around seven feet (213cm) in heels, I don’t exactly blend into a crowd. No one cared. No one cared. No one cared. Well, cared enough to say it to my face.
The best reaction was at a specialty store where the cashiers were assigned to each customer in order. One cashier said that they hoped they were assigned to me because I looked like a lot of fun. That would not have happened if I was in boring shoes.
That sounds like an absolutely amazing experience!
I love the advice as well. Enjoyment is contagious!
Hey Alex,
I sort of did this on a trip to NYC. Wore the skirt craft skirt one day and a true kilt the other day. But I wore boring pants in the plane to the city and on the way back because the last day we went to the 911 memorial and I was worried people may be offended.
I also thought I’d try only bringing skirts/kilts on the trip. But I’m glad I had pants. If you plan appropriately, you’ll have a skirted outfit for most days but a back up “just in case.”
I too feel the increase in mental energy to initiate a skirted outing. It is easier traveling. But I fear a bad outing (meaning a day I wore a skirt and shouldn’t have due to the occasion not because of others thoughts) would set me back a bit.
In the end, I wore two solid days and they were awesome. Went on a windy boat ride one day and wow, almost flashed the Statue of Liberty. But great time. No bad comments.
I want to avoid having a backup “just in case” because I will often find an excuse to use my backup. If I don’t have, then I can’t use it. 😉
It sounds like you had a wonderful trip and a fantastic experience wearing your skirts and kilts though!
Cool, that sounds like a plan. I personally do not organize such trips as I find no reason to do so, I feel safe and comfortable enough in my city. However I’m very likely going in month or two to India and I’m at least planning to go for skirts and dresses, with hot weather being my excuse for leaving pants in the bag. Given that I’m going there because of doing workshops related to the project (and the fact that the company itself writes a lot about embracing diversity etc.) I hope that I will really do it the way I would like it to.
I do feel pretty comfortable doing it at home as well and frequently do so, but I just think that if I were forced to do always wear one because I don’t have any alternatives, the practice would make it even easier over time. I’m glad you feel safe and comfortable in your city though! Certainly not everyone can say that! Your trip to India also sounds amazing!
Alex, go for it! FWIW, as I write, I’m in a a dark green knit dress with front and rear corset-style lacings and a longer back hem; light gray thigh-high socks and black ballet flats. Feels good, looks good. Met our snowplow guy when he came round for a season’s pay – no problems.
And should you drive a distance on your planned vacation, by ALL means do so in a skirt. That is where I most dislike a wad of cloth stuffed into my crotch – it seems to crowd and pinch and overheat more with every added mile!
Great experience! Most people raelly just don’t care at all… or at least too polite to say anything. 😉
I just got home from a 10 road trip, to see the eclipse. Well skirts were all I brought to wear. It was kind of fun as where I set up to watch and take pictures was at a big church with a large parking lot. I made sure I wanked around before it started so as many people would see me in my skirt.
That’s really great! I’m glad you walked around so as many people would see you in a skirt. Exposure to men wearing skirts is extremely important!
Did the snowbird thing for nine weeks this past winter. I took no long pants/jeans. I did pack two pair of shorts and three kilts. The shorts never left the suitcase – I wore kilts exclusively for the nine weeks. I actually ended up coming home with four kilts. We happened upon a Got Kilt store in Savannah, Georgia – my wife bought me a wool tartan utility kilt – it was on the rack and fit perfectly. She does support me wearing kilts. That was my fifth (kilt) clothing choice form her in the last six months (three were for Christmas).
That sounds amazing! Coming home with an additional kilt is exactly the right way to go. I’m glad your wife is so supportive!