Here is a video series from an ex-army professional kilt maker in which he takes a kilt previously made to fit a man, and converts it to fit a woman. In this series he explains how the pleats need to be shaped differently to fit a male vs female figure. For a female, the pleats have a uniform taper along their entire length, while for a male the top part of the pleat is parallel, while the lower part of it is tapered.
This difference is due to the shape of the male vs female body around the hips, and aligns the shape of the garment's silhouette with the actual shape of the wearers body.
https://www.youtube.com/watch?v=r4Fp2eu ... dxijO42-vR
Second, if you look at menswear circa the 17th century and prior, there are skirted, and skirt-adjacent garments *everywhere*. Most of these would fall into the category of 'dresses' nowadays, but they look way more proportionate and flattering than 'a man wearing a woman's dress'. These garments were designed to harmonise with the shape of a male body.
There is an example at the following URL, and countless more in the book 'The cut of men's clothes'.
https://commons.wikimedia.org/wiki/File ... -prado.jpg
The garment shown in the above picture, like the Scottish kilt, puts the skirt fullness in the back, and this is a trend I've seen often in male skirted garments. Also, eliminating the waist split (a 'dress') is often visually advantageous.
From my own observations, the main reason that men wearing skirts typically looks weird is due to garment proportions or garment shape being visually dissonant with the body of the person wearing it. If one understands the cause of those issues, fixing them is trivial. Doing so ideally requires either a garment that is designed for men from the start (like kilts and skirtcraft's garments), or sewing such that one can alter something to fit them better.
Men wearing skirts will not be accepted into mainstream culture while the majority of outfits people (people generally, not the users of this forum), are putting together and posting online look proportionally weird. Actually paying attention to what looks good for one's own body type makes it very possible to find things that look 100% natural for the individual.
There is more to this than 'ruffles vs no ruffles'. There are countless examples of ruffly and decorative garments in male fashion history and a lot of it looks congruent with the wearer and outfit as a whole.
Also, some general awareness of men's fashion history would be extremely valuable. There is little awareness of it vs woman's fashion history in the general population.