skirtcafe.org

Guys Guys.
A dress is no more than a top and bottom in one.
Admittedly certain designs don't work so well on a male torso but there still many which do.
My own 3 go to favourites are pinafore, shirt, tee and polo.
As an entry level dress, the tee design is the easiest option, just a longer or shorter bog standard tee-shirt and sooo comfy in hot weather.
There's nothing wrong with layering a dress either, and I do regularly too. However, try it so the dress element shows, perhaps with a cardigan or a long line shirt unbuttoned.
If you can face the world in a skirt, the dress step is easy and some will even have pleats which would likely pass as a kilt in some eyes too.
Fortune favours the brave!
Steve.

Once you get used to dresses they are much easier than skirts and more fun. There are a lot of styles and you need to work out which work best for you.

Much depends on your shape. If you are slim with an athletic torso (i.e. reasonably muscular but not having overdone the weights) it is quite easy. I am a UK size 12 in a skirt but all my dresses are size 14, which allows for the shoulders.

A lot of styles work well for me, but I soon learned to avoid certain styles, such as wrap dresses or ones with too low a neckline. The fabric is important if the dress will fit relatively tightly across the chest, with jersey being a good choice, although this is less important with looser fitting styles.

I have replaced the wearing of trousers with dresses. The last time in the past fortnight I have worn trousers is to go up on a roof to replace shingles.
With my wife passing away this past April I emptied her closet as her size and styles are not the same a mine. So right now I'm using the space to store my new dresses.
What is amazing to me are the way most women wear trousers instead of skirts and dresses, including church. I wear dresses far more often than the great majority of women, including church.
I'm glad to say I have not been harassed or insulted for wearing dresses. I guess I look enough like a woman for people to accept my.wearing of dresses. The acceptance even stands when I talk with a voice deep for a man.

I like maxi-dresses as I can get away with wearing calf-length socks instead of thigh length stockings or pantyhose when wearing shoes.

John