Postive Wife Support

[KenCT]

My situation is a bit confusing - my wife has said several times that she 'hates' that I wear skirts. Once or twice in the past she asked if I might be transitioning (We have had as acquaintances a trans man and trans woman). This although I wear exclusively men's shirts, underwear, jewelry (wedding ring and a neck chain she gave me); have no interest in makeup or nail polish; I sport a mustache. I do have a few pairs of women's knee socks, because the color choice for men's knee socks seems to be 'black'.
On the other hand, she has gone out with me in public when I was skirted - shopping, eating at a restaurant, walking in the park. She launders my skirts (I do my own socks and underwear, she insists on doing my shirts, slacks, shorts, and skirts because she doesn't think I will treat them with the proper care).
Saturday morning I was getting dressed to go to the local farmers' market. I pulled on my green print skirt, held out a kelly green polo shirt and asked her if it looked OK with the skirt. She said that it did, and nothing further. That really pleased me, because in the past she had said she thought the skirt too short. I hadn't ever asked her opinion about a specific skirt before.
We had a discussion about what fabrics and patterns would not be too feminine. Both of us are OK with denim; I think herringbone and houndstooth are pretty much unisex, and I think she is open to those. I have all those fabrics and intend to make skirts with them.
I'm still wearing Bermuda shorts now and again this summer, just because I have some nice ones and it seems a shame to leave them in the dresser. I think that helps; I hope she gets that wearing a skirt is a preference, not a compulsion.

[Spirou003]

That's indeed a bit confuse. She say that she hates that you wear skirt, but except for that she looks like very supportive! Does she still say it now or was it some weeks/months ago?
What I could suggest (as an endless celibate man), is to sometimes ask her about what to wear today, like "I'll go to the market but I don't know what to wear, do you have an idea?". That way, you will maybe have an overview of the situation: if she never propose a skirt it means she don't like it, otherwise it could be a sign of acceptation. But not to ask too often otherwise it will be weird to her.

[rode_kater]

My situation is a little unusual I guess. So I came at this from the other direction via crossdressing. After a while I decided I like the skirts/dresses but did not really want to present as a woman. The crossdressing was kinda secret, she knew but it was kinda don't ask don't tell. This led to some discussions with my SO where at some point she said exasperatedly "if you want to wear skirts why don't you just wear them? Why do you have to make it so complicated?".

Indisputable logic that.

So of course I've been working from home for the last few months and that has made it easier to wear skirts/dresses during the day. I've been trying to become more comfortable wearing skirts around her. For some reason what random people in the street think of me in a skirt matters much less than what she thinks. I'm also trying to not overdo it. She sees it but doesn't comment, which is good, I guess? We haven't gone out together while skirted.

So kinda positive support?

A side effect is that it makes me look at my collection of skirts with a more critical eye. As long as I was only doing it for myself it didn't matter, but now I consider what other people see. And that has shrunk my set of acceptable skirts/dresses to a fraction of what I have (I've decided floral patterns are not really me, even if I like the colours). I usually browse a nearby second-hand store and went there again to stock up, but it's harder than I thought. In particular, since I cycle a lot it needs be something you can wear on a bike and thus needs some length. However, for my waist size the lengths are IMO mostly too short. My reference is the length of my forearm.

The Skirtcraft skirts look long enough. There is a blue one modelled but apparently they don't sell it?

[moonshadow]

"if you want to wear skirts why don't you just wear them? Why do you have to make it so complicated?".

Male skirting phrase of the decade!

We've all been guilty a time or two!

[Dust]

For some reason what random people in the street think of me in a skirt matters much less than what she thinks.

If that wasn't the case, I'd be concerned.

The people we love are the ones who really matter. We shouldn't get too concerned over the random people who see us at the store, but the people we love are another story.

It's kind of like how we dress up for special events, be it a wedding, funeral, church on Sunday, or date night. We stop and think about how we look, on a level we wouldn't normally, because we see it as important.

[BobM]

My wife and i were in Hendersonville ( NC ) today with some long time friends from Florida. I'm always in a kilt or utility kilt when we go out, and it is rare to get any sort of comment at all. Today there, were two things that were fun. First, we were outside an upscale resale shop and my wife says, "Let's go in. Maybe we can find you a skirt". We looked, but I didn't see anything we both liked. A bit later we were crossing the street and there was a middle aged woman on the opposite sidewalk. The look on her face as she,spotted ne was about as sour as sour gets. As we passed her I said, quietly, "Be careful. Your face might crack", and keep right on into our target bakery.

I've been wearing skirts/kilts for decades and have never had a single bad experience. A few cat-calls, strange looks, and such, but nothing really hostile.

[Dust]

A bit later we were crossing the street and there was a middle aged woman on the opposite sidewalk. The look on her face as she,spotted ne was about as sour as sour gets. As we passed her I said, quietly, "Be careful. Your face might crack", and keep right on into our target bakery.

That reminds me of the old Calvin and Hobbes comics where he would make faces, and his parents told him to stop because it might get stuck that way. He paused, thought about it, and when right back to making the faces in the hopes that it would get stuck that way!