I've been hiding out here in a dark corner as a guest for the last half year and I feel its about time to make my presence known. You all seem to be a good fellowship and similarly inclined as myself. I'm 36 years old and live in a small town in the mid-Swedish country side and work in a hospital.
It all started the first time I was home from school alone, age 8-9. I found a yellow dress of my sisters in the laundry hamper and tried it on... And loved the feeling, nothing constricting my waist or trying to slide down and it was fun to spin around in. I kept it a secret, not really the right family to do otherwise. As a teen I got two dresses from a friend id confided in, proper A line ones with a 240cm hem. I spent a lot of nights solo camping in a tent out in the woods just to lay around in them reading sci-fi books.
Then as so happens, life got in the way, I did my Military service year, moved out, got a degree, married a girl, bought a house, had a kid and time ticked on, I was so busy that my love for dresses was mostly forgotten. Then one day, about a year and a half ago we were all out of the normal
scrubs at work, but there were dresses left, I donned one with the normal scrub trousers under and the memories sure came back, we were 5-6 lads in dresses working the ward that day! Of course I sent a picture to my wife and we had a good laugh about it. A few months later she asked me to be a living dress form and I obliged, she was making a full circle skirted dress, so I had a twirl while it was pinned on me and the bug bit me again, just a little bit harder this time.
After secretly trying on most of her dresses for a month I had to talk to
her about it, this time it was here to stay. I knew she would be kind of
supportive, but we had a very, very rough patch, she was convinced I was
going to come out some rainbow variant at the end of it all and her anxiety
got the better of her. But I think I'm starting to turn her around to the
notion that it is just clothes and I sure look a lot better when I make an
effort rather than the usual joggers/jeans and a oversized tee/jumper.
I started wearing the dress scrubs at work one year ago, though still over trousers(as I'd rather not get blood or worse on my legs/tights). I meet a lot of people at work which has helped my confidence a lot and just help build up a norm. The first week one colleague tried to tease me about it twice("Ah, its a long shirt day today!") but the third time he saw me in it he said nothing. A few compliments and quite a few smiles but so far not a single bad comment or even look.
I have a few tunics and sweater dresses that are(IMO) too short to wear without trousers/shorts under and I have not made it out (visibly) in public in with the dresses that are long enough, but with a jumper over they look like a skirt but with the comfort of a dress.
My wife convinced me to buy a kilt (well not a real wool tartan one, a cheap cotton/poly one), I'm hoping it can be a good bridge to get both her and me used to me being beskirted in public without trousers. Its a wrap skirt in a plaid pattern with some half-hearted pleats rather than a Kilt, but I better not tell the missus

I think my preference is still dresses, I like that they hang from the shoulders so they don't fall down even with laden pockets and there is no belt/elastic/tight fitting etc around the waist that feels awkward when sitting down(my waist and hips are almost the same measurement, so its hard to get things to stay where I want them). I like the hem to right under my knee and A-line. If it was entirely up to me I don't think I would wear anything else as main garments anymore, just complement with tights, jumpers/jackets as needed, but I'm not quite there yet.
Wow, that was long! But maybe one of you will find it an interesting read.