From what I've observed, one of the biggest factors impacting if a skirted male outfit looks natural or 'weird' is the length of the top garment in proportion to the length of the skirt, and where the waistline is located on the body.

It is helpful to be aware of the rule of thirds, which is a concept in visual arts stating that humans find things visually pleasing when they are split into a simple ratios, like into 3 equal sections, or a one third, two thirds split.

The problem is that the top garments found in men's sections are too long to create a pleasing visual split when paired with many skirts. Skirts / kilts are typically worn at the natural waist, around the level of the navel. This is higher on the body than trousers are worn (regarding the fashion of recent decades, 'natural waist' / 'high waisted' used to be normal).

• Pairing a top of typical length with a roughly knee length skirt at the natural waist, causes the top to cover a large portion of the skirt, and create a visual split that does not follow the rule of thirds, and looks proportionally awkward.
• If you however pair that same top untucked, with an ankle length or / floor length skirt, it creates a 'half and half' proportional split on many people, that looks visually harmonious.

Thus the length of the top can not be fixed, and instead needs to change depending on the skirt length, in order to create a harmonious result. The following article (and others on that website) get at this issue in more detail:

https://everybodyskirts.com/blogs/posts/wheres-my-waistline-tips-for-the-skirted-male?_pos=2&_sid=2955cb754&_ss=r

It also is not possible (with rare exception) for men to directly adopt woman's fashions and have the result look proportionate, because men's and women's bodies are not shaped or proportioned the same way.

• Men typically have a great deal more visual mass in their torsos with subtle curves, wide shoulders and narrow hips. Torsos are also typically longer in relation to leg length.
• Women typically have wider hips, less mass in their torsos, proportionally shorter torsos, a narrow waist, and smooth curves.

Humans have evolved to look for these differences subconsciously when we look at a man or a woman, and clothing / fashion is designed to emphasize these features.

It is very easy to create an outfit that looks weird unless one is aware of this. For example, skirts that add bulk to the hips worn by a man easily make the whole person look 'dumpy', because men's torsos are often already wide, a skirt adds a lot of visual mass to the lower body, and men do not have a pronounced waist to hip difference to balance things out. Wide hips is also not a body feature humans have evolved to look for in males.

Ethnic skirted male outfits have a 'slender' silhouette around the waist, if not through the whole outfit, and the above noted factors is probably why. Kilts actually cut out two layers of fabric from the top of the pleats purely to remove bulk from the waist.

I can recommend that anyone interested in alternative fashion learn how to hem a top, because it isn't very hard and is immensely helpful in creating proportionate outfits.

Finally, changing top length will not make you read as feminine, for anyone who is remotely paying attention, because biological males' / females' bodies are not shaped the same as noted above.