First time would've been when I was around 3 or 4. So, sometime in the late 1970s. Didn't like it at that time, probably because both my mother and sister were pointing and laughing after putting me in an old dress that my sister wore when she was my age. Guess the dress didn't look right with the brown boots that I wore back then. First time I tried one on my own was in '91. Found that there was a skirt left on the dryer at our old house, so slid it on to try it out. Liked the comfort.
In late 2000, I switched from long trousers to shorts as my usual attire, finding them more comfortable, even in the winter. A few months later, bought an ex-MOD MacKenzie kilt off the 'bay, and figured I'd lose weight to fit into it. I kinda doubt I would've been able to shrink 10" off my waist to have fit it. Anyway, after buying that, I eventually decided to try out skirts again. Bought a few in early February 2002 at a thrift store, as well as a dark brown knee-length number off eBay. Started wearing publicly on February 14th, 2002. Family didn't like it at the time (took them about 10 years to realize that it really wasn't that big of a deal), but sorta accepted tartan kilts when I started wearing those in August of that year. A couple years later, got my first UK from a former member here. Then, soon afterward, started working for Utilikilts for a few months. I still did wear normal skirts, frequently as a slip under the wool kilts to make them more comfortable.
In the summer of 2009, it got too warm for kilt wearing, so I started wearing lightweight skirts in public again. Also discovered that I became less of a "sore thumb", so I could take care of business without being stopped every few minutes by someone who wanted to know if the highland games were going on, or where I came from, etc. Liked that. So, I relegated the tartan kilts to special wear only, and last wore one in 2011. Not sure if I want to go back. I know that one of the 9 yarders I own would fit me, but, I have zero desire to wear it.
In 2013, I started wearing dresses again. Mainly around the house as sleepwear, but eventually started wearing a couple out, but usually covered up, so they looked like skirts. Took a couple years to get to the point where I'd be bare shouldered in public, although, not while going into stores or into restaurants, etc... But, while driving, etc, yes. For the past four years, when I've been doing a solo roadtrip somewhere, I've been either in a dress, or a top and skirt combo. Over the past year or so, especially after I started having the fur on my back removed every 5-6 weeks, I've started regularly going out and running errands bare shouldered. And, now, with the virus, I do it all the time. I *rarely* have a sleeved garment on when I'm in public. I suspect that, once the virus passes, the only times I will be sleeved will be with family, at a couple places in the area, or when I'm employed again. If I decide to start dating, I probably will be wearing a dress (as a guy, of course), since they're the perfect bozo filter. Even better than a skirt or a kilt.