Why men should wear dresses in heatwaves
A dress of the correct design, is among the most comfortable things that anyone, regardless of gender, can wear in hot weather.
Humans are cooled by sweat evaporating, and for this to happen airflow is needed. A lose-fitting dress in the right fabric is fantastic because hot air rises: air can flow up through the skirt, around the torso, and out through the neckline unhindered.
And unlike shorts, a long dress also keeps the sun off the body, and does not trap hot air around one's crotch
But men look weird in dresses
Actually, no they don't. See for instance the Thobe from the middle east, Kurta from India, the cassock, and medieval tunics.
All of the above are examples of men's garments that most people in the west would consider 'dresses'. Yet, they work harmoniously with a male body, because that’s what they were designed for.
The reason why dresses can look odd on men is principally because of men wearing garments that were designed to show off the shape and features of a female body. It is not difficult to design dresses for men from the start, which, as the above examples show, do not create this problem.
How to find hot-weather dresses that work on a male body
Ideally, one would be able to walk into the men's department of a clothing store and find dresses that are comfortable for men to wear during a heatwave. Unfortunately, western cultures aren't there yet. There are a few options:
Selectively choosing women's garments
It is possible to find garments in the women's department which avoid the previously mentioned fit issues. One wants to look for garments which do not include shaping for a bust or narrow waist. Examples include:
T-shirt dresses
A T-shirt dress is literally just a long T-shirt. They are usually rectangular cut, like a normal men's t-shirt, but are longer.
Find a garment that fits in the shoulders, and the rest will 'just work' for the most part.
Trapeze cut tunics / dresses
A trapeze cut dress is a garment that is fitted in the shoulders, and flares out in an A-line shape from the shoulders down. They typically have no shaping for a bust, or waist.
These kinds of garments rely on fabric drape to fit the body, as long as the shoulders fit, the rest also will.
Trapeze cuts work especially well in heatwaves because they flow as you move, promoting great air circulation
Ethnic garments
Another option of dress-type garments for a male body, are ethnic garments like the thobe and kurta mentioned earlier. These garments are widely available in male sizing.
The thobe for example is a garment from the middle east and northern Africa. The garment is well adapted to hot weather because the countries where it is traditionally worn have hot climates.
An issue with wearing these kinds of garments is that in Western countries, they are mainly worn by people of specific cultures and / or religion. Wearing the garment is liable to imply that one is a member of this cultural group.
From the surface-level research I have done, they are not 'closed' cultural garments. However one should be aware of the potential for cultural association, and make their own choice if they feel it appropriate.
Drafting and sewing your own dresses
Dresses are actually one of the easiest kinds of garment to design and make. A rudimentary sleeveless dress can be constructed from two rectangles of fabric and 4 seams, leaving spaces for the arm holes and neck.
One can refine fit by introducing shaping to the pattern pieces. I'd recommend looking up how to draft and sew a T-shirt, then make it into a dress by lengthening it.
There is a considerable amount of information available online about sewing and garment construction.
There is also a considerable amount of unexplored possibility space for designing men's skirts and dresses. As of writing almost nobody is doing anything in this space.
A kilt is not the answer - a sarong would be better
People may intuitively jump to 'wear a kilt', as it is the de-facto standard male skirt, however, a kilt is not a good option for hot weather.
Kilts are constructed from 5 to 8 yards of heavy-weight wool fabric and are very insulating.
Instead, a sarong or lungi would be a better idea. These are a rectangular length of lightweight cotton fabric that is wrapped around the body and tied in various ways. They are much cooler due to the lighter and lose-woven fabric.
A lightweight dress can be better still, given how eliminating the waistband allows air to flow from the bottom of the garment and out of the neckline.
Skirts are not innately cooler than shorts or trousers just because they have a big hole in the bottom. They can be cooler due to their flowy nature, but it depends on the fabric and design of the garment.
Hot air rises. If it has nowhere to go due to a garment made from a thick dense fabric, attached to a tight waistband or bodice, the hot air will pool inside the garment unless the person is moving around a lot.
Skirts can actually be warmer than trousers because of how they trap the air around both legs within a single volume. Energy loss depends on surface area, and the surface area of the skirt can be less than that of two separate trouser legs. This is similar to how mittens can be warmer than gloves.
Skirts constructed from a lot of fabric are also insulating just due to the volume of fabric. It will fall into folds or pleats which themselves trap air, like a double glazed window.
A note about materials
What a garment is made from also matters a lot in its comfort during a heatwave. Especially, polyester-based fabric should be avoided entirely.
Polyester is plastic, and wearing a garment made of polyester will be like wearing a plastic bag. When you sweat, it will be trapped and pool within your clothing, making you sticky and uncomfortable.
Instead, look for natural fibres like cotton and linen. Semi-synthetic fibres like rayon (viscose), are also comfortable in hot weather.
Linen is especially good at carrying away and quickly evaporating sweat, keeping you cool. Cotton by comparison tends to absorb and hold on to moisture.
Summary
A dress of the correct design, is among the most comfortable things that anyone can wear in hot weather. I find it exceptionally silly that men in western cultures have been denied access to this basic form of clothing in recent times.
Yet, in most cases there is nothing stopping men from wearing these kinds of garments. By wearing dresses that are designed to harmonise with a male body, the awkwardness that often arises can also be avoided entirely.
It is possible to find dresses that will work on a male body be selectively choosing women's garments, or wearing ethnic garments. Failing that, they can be made with only rudimentary sewing skills.
All it would take to normalise, is for more people to try it.