The road to not caring

[Methylcyclohexane]

Hello everyone, newbie here. You can read my introduction over on the Introductions forum to learn a little bit about me.

As of the time I am writing this, it's the night before Thanksgiving and I feel like I'm coming down with a cold or something, which is very unfortunate timing. Fortunately, it doesn't seem like it's going to be *too* bad. I think I'll be able to tough it out, but I'll probably stay home over the weekend instead of visiting family. Instead of feeling sorry for myself though, I'm going to keep myself entertained, and perhaps entertain you all with a simple story from the other night.

I live alone now and own several skirts as well as a dress, plus a few pairs of tights. I did wear one of my skirts in public once this year, in summer. I went to a vintage clothing shop in a town about 45 minutes away. It was advertised as being very inclusive and friendly and was far enough away from where I live that I thought it was unlikely I'd see anyone that I know. I showed up about a half hour before closing time I believe and was greeted by the store owner, who did a double take at my outfit but smiled and complimented it! She was the only person I ended up seeing the whole time I was there. It was honestly a pretty nice experience.

After that, though, I had never worn any of my skirts out in public again. I live in a small town and I randomly see people I know while out and about with quite a high level of frequency, which made me feel very nervous about being recognized and prevented me from skirting in public again.

Still though, I couldn't help thinking, "what even is the point of buying new clothes if I'm not going to even wear them outside?" So, I decided on Monday that I would. I picked out a long skirt appropriate for fall and put it on over a pair of fleece-lined tights. As for footwear, I wasn't sure what to do. It was a pretty chilly evening, so boots would have made sense, but the only boots I have are camo, which I felt didn't match the outfit, but neither did my sneakers. I ended up choosing a pair of black dress shoes I own as I felt they matched my outfit best, even though boots definitely would have been better suited to the temperature.

I set off sometime after the sun had set (to help minimize the chance of being spotted by someone who was not a stranger) and headed for Dollar General... But got overcome by nervousness and drove right past it, aimlessly. I decided to turn into the parking lot of my local Walmart, stayed there a couple minutes, then headed back home. Before I got there though, I decided to pull into a Wendy's. I considered parking and going inside since it looked almost completely dead inside, but I was still quite nervous. However, I did go through the drive through and order a meal. I'm not sure if any of the workers at the windows could see that I was wearing a skirt, but if they could, none of them seemed to care about it or react to it.

After I got home and ate my meal, I resolved that I would conquer my fears and actually go inside a store this time. At about 7:30 PM, I left for Dollar General again, and still got overcome by nervousness, but this time I had made it to the parking lot, where I just kinda waited for a while. Which honestly probably would have seemed very creepy to anyone who may have noticed, which would NOT have helped my desire to just be seen as a normal person! Eventually, though, I somehow worked up the nerve to actually go inside and buy a couple items. I felt like I got some stares and weird looks, but I actually couldn't tell you for sure because I was trying so hard to avoid eye contact. After picking out the only two items I had come for in the first place, I bought them at self-checkout and was on my merry way back home (again).

As I was walking from my car to my apartment building, I felt like I was in the clear. I had done the thing I had been too nervous to do for so long, and nobody I knew had seen me! But just as I opened the door to my apartment building, who should I happen to see but my next door neighbor, Jack! To be honest, it did spook me just a little bit, but only because my nerves were still a bit high and also it was dark out like I mentioned.

I just said "Oh, hey" or something inconsequential to him after recovering from my momentary surprise and he said something equally unremarkable back. I did notice what I thought was him beginning to peer down, as if to try and discern whether I really was wearing a skirt like it seemed, but I just walked on in and up the stairs to my apartment. In any case, Jack didn't linger or try to make conversation with me or anything, so that was my night.

I've always heard that, as long as you're not hurting anyone or anything, you should just do whatever the heck you want to, and darn all the critics! It is something that I agree with in principle of course, but it's also a lot easier said than done. I'm not yet at the point of not caring at all about what others may think and letting it affect me... But I feel like I'm making the right steps toward it.

Link to a picture of my outfit:
https://imgur.com/a/Y0hhfnr

[Procellis]

The road to not caring is long, winding, and full of blind turns. I empathize, and have felt, every emotion you experienced.
I expect there’s a matter of doing it consistently enough to build the muscle memory of confidence. I went a while without a skirted excursion, and that first outing sure felt like everything you just shared, even after having done trips where I mainly wore skirts without any issues. Well, there was the time I let my nerves get the best of me and I didn’t pay attention to the gap in bench seating at a restaurant. Trying to slip out of the place without causing a scene fails when you fall off the chair. Anyhow, most recent outing, a Harley dude gave me a hard stare as he rode by, but that was the extent of anything notable. But it was still a nerve wracking experience.

[TonautBrom]

Well done Hex - you got out there, you did it and you survived. I’m still pretty early in my journey but each time it gets a little easier. I’m storing up the thousands of uneventful interactions for the day I have a negative one - which will enable me to be certain they have the problem, not me.

(So far just one incident of note, and that was quite fun really. Getting off a bus in London on a hot day a man just said, wide-eyed “You’re wearing a skirt!”, to which I just smiled and said “Yes it’s very comfortable”, and went on my happy way.)

[Coder]

It should get easier as time/experience builds up, but being in a small town sounds like it can have some drawbacks. Eventually, in your own time, you’ll get there!

[Bee Guy]

Kudos for getting out! I have yet wear my skirts out of the house. (And probably won't for some time since my beloved wife insists that skirts stay in the house when they're on me. )

By the way, I like your skirt. I have a very similar one, that I like very much, which I ordered from Amazon.

[Ozdelights]

Well done already. I know the feelings you are going through. I live in a small town and have only spoken to a couple of people here while skirted. I am finding it easier interacting with other people while away from home. So far only positive interactions. It usually gets easier with experience. Have fun.

[Myopic Bookworm]

Nice skirt.

[shadowfax]

Well done on taking your first steps out into the world outside of your apartment, Hex.

If it is of any help or encouragement to you or others, I described my own first steps outside, six years ago, in a thread on this forum.

I wore medium-height, block-heeled shoes that first time.
I like to wear heels with my skirts as I am a little below average height for a man.
I now usually wear high heels when skirted (3" (75cm) or a bit higher).

[Jim]

Sounds like a decent first time out. The outfit looks good, not stealthy at all but not looking like you are trying to pass as a woman. (The beard helps!) My avatar shows how I first wore a skirt out in public.

I live in a small village myself, population about 750. I'm out in a skirt almost all the time and have had no negative reactions from neighbors. Once, on Facebook, I made a comment about "sexual orientation" and got a response from someone I don't know in our village, "we all know what your sexual orientation is." So maybe there's some gossip. Or did he know I've been faithfully married to one woman over 40 years?

[denimini]

A well coordinated outfit. The beard does help dispell any illusions of being anything other than a man in a skirt.
The first outing is always the hardest and it just gets easier from there on. You need to psyche yourself up that you are wearing the most boringly normal attire and portray an air of total confidence and nonchalance; that sets the cue for others. Eventually it will become natural.

I also had misgivings about going public in the local community but eventually had to face it. The upshot is that once locals get used the the new attire it is not novel anymore and becomes normalised whereas trips away are where you often get a second glance by strangers.

In the end you will miss the adrenaline rush.

[KiltedBigWave]

Good to hear your getting out! Enjoy it.

[Methylcyclohexane]

Thank you all for the positive feedback and the compliments on my outfit! A little update on being sick: I think I actually have a flu, not a cold, and right now I'm feeling pretty sapped. It might also be Covid, which I'm hoping is not the case. I'll take a Covid test later, but right now I have so little energy, I think I'm just going to stay in bed a little while longer. Again, thank you all for the positivity; it really does make me feel just a little bit better on an otherwise crummy day.

[skirtyscot]

Well that is a pretty normal range of events and feelings for a man's first few times out in a skirt. You've tried picking a place where you're less likely to get a bad reaction. You've tried going somewhere that you won't meet anyone you know. You've chickened out then girded your loins and gone ahead with it. You've bumped into someone you know and disappeared in 2 seconds while trying to give the impression that everything is normal. And you're not discouraged! Keep going; it will get easier.

Nice skirt. Long skirts are immediately noticeable but they seemed to me to be the obvious choice for someone who's used to covering his legs but wants something which is designed to be kind to his delicate parts. Also the way they move is a lovely contrast to trousers.

[Modoc]

Nice skirt. Long skirts are immediately noticeable but they seemed to me to be the obvious choice for someone who's used to covering his legs but wants something which is designed to be kind to his delicate parts. Also, the way they move is a lovely contrast to trousers.

It took me a while to get into longer skirts and dresses even though I was ok with knee length and minis pretty quickly. As is way too often the case, I let myself self influenced by the opinion of those who adamantly proclaimed that longer skirts were too feminine for men. But having decided to push the boundaries even further I found some longer skirts and set out in them and now wear them probably more often than the shorter ones.

[Faldaguy]

I'm not trying to hide in my skirts; so my picks are simply what strikes my mood and the activity -- plus while in this 'frozen north' what is warmer -- and long skirts are an easy answer. Combine a decent long lined skirt, or skirt with slip built-in; and your own half slip and decent socks, you are as well armored as with any pants. Sure, it is a bit more noticeable, but still nobody says boo. Just remember to watch your hem!