I've really been pondering (getting back to masculinity in skirts here) ways that a man can present himself as dignified, gentlemanly, relaxed, and comfortable in a skirt. I seem to have come down to a few general "principles" that I'm going to experiment with at the sewing machine this winter.
I think the skirt needs to be somewhere around the knee, like a kilt. It should somehow be pleated and fairly full (A-line), it should be belted. It should be a neutral solid, tartan/plaid, or a grey brown tweed.
On top. Whatever we wear on top for formal wear should expose the belt...like a traditional vest, or a cutaway jacket along the lines of a traditional kilt jacket. I would stay away from a tailcoat though - tails over a skirt seems strange. For casual wear, just a nice matching/contrasting shirt, or a shirt and sweater either sleeveless or sleeved depending on weather and tastes. Normal male necklines.
Footwear, depends on weather obviously...although sensible leather walking shoes do me year round for casual wear. shoes must match the belt and both must not clash with the skirt/top combo. I'm not a fan of boots other than for work, save them for the utilikilt look. However, genuine green rubber Gates "Wellies" (from Scotland)go famously with a tweed skirt.... out walking the dog or working around the yard, mucking out the stables.
A tweed or plaid flat cap might go well, or even some other brimmed hat. I'd stay away from ball caps. Or go bare headed. Carry a walking stick if you wish.
Anyhow, this is where I'm at in my mind's eye. I spent hours poring over pictures and then scanning ebay and the web for "looks" that yelled 'Country gentleman" and I wound up mainly looking at ladies' skirt suits of the softer tweed variety. "Quiet Man Lite" look. We can go for a hulky gladiator braveheart look, or a more refined gentleman farmer tweedy look. My physique tends more to the wimpy gentleman look.... So that is going to be my focus for the next while as I experiment. I'll wear my own design "Workilt" for work and shock the ladies!
