I just recently came across this community and I’m very interested in digging into some of these threads and conversations to learn more!
Who am I? I’m a middle aged man, working in a male dominated, technical engineering field. I’ve been interested in skirts for years, but it hasn’t been until the last year or so that I seriously considered actually wearing them myself. This may be part of my mid-life reimagining process (not to be confused with a mid-life crisis!) I now own two skirts - both ankle length with lots of fabric that can flow and spin beautifully! (My favourite kind of skirt!)
So far I haven’t yet worn skirts in public, since I need to give my wife some time to get used to the idea first. I’ve had years to think about this, whereas I’ve only just started discussing this with her recently. She is, understandably, a bit worried about “what will people think”, and I don’t want to add more stress to her life that is already full of other challenges. However, she is generally supportive, and I think we’ll get there eventually. I can be patient! My young-adult daughter, by comparison, is my biggest supporter and we have started discussing various sewing projects that we would like to start doing together!
On that note - I do enjoy a craft project, and have dabbled in sewing over the years. Usually my imagination is much bigger than my abilities (as it likely is for most people, I’m guessing!) but I think that making and/or altering a few skirts should be well within my grasp if I don’t expect my first try to be perfect.
I’m not at all well versed in “fashion”, and for that matter, skirts for men in western culture is such an unusual thing that I’m not sure there are any fashion rules that apply anyway. [I’m sure there are opinions in this forum that will prove me wrong!

As for styling, I flip-flop between a feminine, light weight flowing style or a more masculine, heavier weight style with pockets, a working fly and belt loops. I see how both could fit into my lifestyle, since, as much as I like the long flowing options, they can be impractical due to their tendency to snag on corners or get underfoot on stairs.
To get started in public, I’ve been trying to find a skirt that fits the following criteria:
-Budget friendly
-Not flashy (solid colour, simple cut lines, no frills)
-Waistline similar to a pair of dress pants, with a functional fly, belt loops, pockets, etc
-Mid-calf length, or at least past the knees
-Slight widening at the bottom (A-line) for ease of movement. No slits!
I’m imagining wearing this as a straight replacement for a pair of pants, paired with a short sleeve, button-up, un-tucked men’s shirt + sandals in summer, or a sweater, long socks and shoes/boots in winter.
If you have any suggestions, please feel free to share! I’m also considering a sewing project to convert a pair of pants, but I’d like to find some examples for guidance so I don’t have to make all the mistakes myself first.
I could share more, but I think this is long enough for an intro, and I want to start cautiously with how much personal information I share publicly.