The most common reasons why 'man in a skirt' outfits look awkward
Since writing the article Skirt silhouettes and styling for men back in 2024, I have continued to observe outfits in passing. I've been observing which outfits look natural on the body, and those which subconsciously look strange to me.
In doing this, I have noticed some trends among outfits that look awkward, which are listed below. These are easily addressed once one is aware of them.
Within this article, I use the term 'skirt' as gender-neutral term for all garments covering the legs with one section. The term 'kilt' I use to refer to the Scottish garment and direct descendants, a wrap skirt with a flat front and pleats in the back and sides.
Why skirted male outfits often look awkward
Men haphazardly substitute trousers for a kilt / skirt
A trend that I have noticed is that men often substitute their trousers or shorts for a kilt or skirt, changing nothing else. about their outfit. Most outfits assembled in this way look awkward to me.
How to fix it: learn how to assemble outfits
Like all visual arts, outfit styling depends on some core rules. Garments must have proportions and lines that work together, and the outfit as a whole must work harmoniously with the body within it.
Menswear as a system is designed to work collectively, in a way where you can just take different garments and put them together quite haphazardly. The result looks OK because the proportions, colour pallets and cuts of these garments is so limited.
If you introduce a skirt into the mix, this ceases to work. Skirts and trousers have different shapes and read differently within an outfit. Just substituting pants for a skirt typically leads to outfits that look awkward, because they break styling rules.
You can avoid these problems by learning how to style outfits. There is a considerable amount of information about this on the internet targeting both men and women. I would advise engaging with both, because it will give you an understanding of how to style outfits for a male body, and also how to draw from the the artistic expressive elements within women's fashion.
Male and female bodies are not the same shape and rarely style in the same way. It is not generally possible to copy woman's outfits verbatim onto a man, and end with something that looks natural. However, women's fashion is still a treasure trove of information if one knows how to learn from it.
The goal is to observe how women approach foundational things like pairing colours, proportions, and how different garments are layered. One can also learn from the styling process, such as 'this does not pair well with this, so I am changing it to X'.
Garment pairing matters a lot. As we will address shortly, a big problem in many 'man in a skirt' outfits, is that most menswear tops pair horribly with skirts.
Men assemble outfits without awareness of body proportions
A common problem in male skirted outfits is assembling outfits without paying attention to body proportions. Men are not all the same shape, and the same garment won't read the same way on all people.
A very common problem is for an outfit to look top heavy. Many men often have wide shoulders, which if one doesn't account for in outfit styling, will make an outfit look top heavy.
There is a picture online of the star treck male 'skant' costume that is a good example of this. The outfit looks top-heavy because the skirt is too short.
How to fix it: reserch dressing for your body type.
There is a lot of information on the internet about dressing for your body type.
Men intuitively wear skirts too low on the body
The 'waist' is the narrowest part of the torso. It is clearly visible in most young men and women, though may become less apparrent with age. Typically it is slightly above the navel, though is generally higher on the body for women than men.
The 'waistband' of most men's trousers produced today does not sit at the waist, but lower on the body around the middle of the hips.
Many men who try wearing a skirt intuitively wear the garment at the trouser waist. Wearing a skirt that low tends to create an optical illusion that makes the person's legs look shorter than they are, creating an awkward or top-heavy appearance.
How to fix it: raise the waistline
I would recommend that people who are new to skirts wear them at the natural waist, at or slightly above the navel. This is where kilts are traditionally worn, and there are many kilt wearing tutorials that show where this is on the body.
As you gain experience with styling it is possible to raise or lower the waistline from the natural waist, but doing so requires changing other aspects of the outfit. This will be discussed later.
Moving the waistline up or down will not make you look feminine!
I have encountered various concerns raised by men online that moving the waistline higher will make them look feminine.
This concern is ungrounded. Male and female bodies are not the same shape, and people largely read the sex of a person from their body and face shape, not clothing.
Men's Kilts are almost always worn at the natural waist. If you look up pictures of men in army pipe bands, i doubt they look remotely feminine to you.
Most menswear tops are too long to pair with skirts
A critical aspect of styling outfits is balancing proportions between the top and bottom. People generally like proportions that fall into a simple mathematical ratio like 1:1, 1:2 or 1:3.
Most menswear tops today have a length designed to split the body into two equal sections when paired with full length trousers. The top garment takes half the height of the person, and the bottom takes the other half.
Tops of this length can pair well with ankle or floor length skirts because the relative proportions remain the same. However, they don't pair well with shorter skirts.
Pairing a typical length menswear top garment that is untucked, with a knee length or shorter skirt splits the body awkwardly. The length of the top covers much of the length of the skirt, and is dominant within the outfit.
As men typically already have substantial mass in their torsos, typically with broad shoulders, it creates an outfit that looks top-heavy in an awkward way.
How to fix it: tuck in or crop your top
The length of your top needs to change depending on the length of the skirt you are wearing. This can be done in 3 ways:
- Tuck in your top. Doing this shortens the length of the top portion of the outfit to where the skirt waistband is. You can raise or lower where the waistband is on your body to make small proportional adjustments.
- Crop / cut your top. Wearing a shorter top garment allows it to be worn on top of lower body garments without swamping them. Crop top does not mean so short that it shows skin. Depending on where it is cut, you can create different proportions.
- lower the neckline on your top. Wearing a top with a lower-cut neckline also reduces the apparent size of the top of your outfit.
Kilt jackets provide a good example of how shorter tops look on men. They are cut shorter than typical suit jackets, such that the jacket and kilt are about the same length.
As noted, people tend to find things attractive when their proportions relate by a simple mathematical ratio:
- Top and bottom with equal length. Long skirts pair well with longer tops. Typical length men's tops result in a 1:1 split paired with pants or a floor-length skirt. Wearing shorter skirts with shorter tops maintains the same proportional relationship.
- Bottom twice as long as the top. With longer skirts, a shorter top produces a one third, two thirds relationship which makes the legs look longer.
For more examples of proportional balance in play you can look at how women style skirts, they vary the length of their top as needed to create the proportions they want in an outfit.
Women's clothing departments include garments of different lengths, so that they have the needed options to do this. Menswear desperately needs more varied top garments for the same reason.
In the meantime, cropping a top is easy, and learning to do so massively expands your options.
Another hack is to utilise colour blocking. When different parts of an outfit that are touching each other have the same colour, they read as a single part. For example you can wear leggings or tights that are the same colour as the skirt, which unifies the bottom of the outfit into a single block.
Boxy cut tops create a 'straight up and down' visual line that clashes with flared skirts.
A silhouette is the outline of a shape, and the eye will tend to follow the lines of this shape. For example a typical rectangular cut men's shirt will guide the eye to follow a straight line up and down.
Outfits work best when the silhouettes of the different elements speak the same language. For this reason, a straight skirt like a sarong can pair well with the silhouette lines created by the boxy cut of most menswear tops. The silhouette of the skirt and top both lead the eye in an up / down direction.
However, a straight cut top paired with a flared / A-line skirt looks clashy to me. You get a harsh angle where the top and bottom of the outfit intersect.
How to fix it: wear tops that have shaping in the side seams.
A-line skirts often pair well with fitted tank tops tops, which reveal the innate curves of the body. Flared skirts also pair well with structured tops that have a curved shaping in their side seams. In both cases, the curved line then gently guides the eye into the flare of the skirt.
Some men, commonly older men, have a very straight-shaped 'cylindrical' torso. In this case, the second option of a structured top garment will tend to work better. Such can create its own shape by being tight to the body in some places, but standing away from the body in others.
Straight skirts also pair very well with a straight torso.
Women often wear boxy t shirts with skirts, why doesn't this work on men?
Male and female bodies on average are not the same shape. Female bodies are typically shaped like an A, wider in the hips with narrower shoulders.
When such a woman wears a boxy cut top, the fabric drapes over and takes on the shape of the body beneath it. Due to the typical shape of the body, this creates a flared silhouette that leads the eye into the flare of a skirt.
It is not possible to copy woman's styling directly onto most male bodies, the result will not look the same.
Many skirts have female body curves embedded in their design.
Having been culturally viewed as female attire, most skirts avalible at the time of writing are shaped to fit around, and / or exaggerate female body curves. When a man wears those garments, they impose an unnatural shape onto the body.
This can look very strange because the upper part of a male and female torso are shaped differently. People subconsciously read 'female hip curve' and expect to see a female torso shape above it.
When the subconscious sees a female hip curve with a male torso shape, it recognises this as erroneous or unnatural.
How to fix it
One needs to pay attention to how a garment is shaped in the waist and hip area, and ensure this makes sense for their body shape.
A traditional Scottish man's kilt, and a similar length skirt designed for a woman are shaped differently.
- The kilt flares linearly from the waist to the hips and down.
- The top part of the woman's skirt will have a pronounced curve in the silhouette between the waist and hips, hanging straight below this point.
- Anything that is tailored or fitted, such as pencil and A line skirts, will have a female body curve in their construction. The strength of the curve will vary, because some women are straighter in silhouette than others. Most of these will look strange on men, but some may be passable.
- Skirts that are made from a gathered rectangle with an elasticated waist will generally work on men, as long as the ammount of gathering is not adding too much bulk to the hips.
- Men's clothes are typically made with stiff fabrics, with little to no detailing or ruffles, and have muted solid colours.
- Woman's clothes are typically made with thin, drapy flowy and often shiny or textured fabrics. They often include ruffles and other details, bright colours and loud prints.
If one is making their own garments it is straightforward to compensate for this. Men's kilts, utility kilts, and skirts which are produced with a male body in mind (such as those from 'skirtcraft') will have made appropriate choices here.
Unfortunately, the majority of skirts being produced at this time are made with women in mind, and a lot of care is needed to find garments that avoid this problem.
Finding garments that work would be much easier if garments were made and sold targeting men.
Menswear and womanswear garments use different types of fabric, prints, and colours that often don't pair well.
Because men wearing skirts are currently primarily wearing garments made for women, they are combining men's and woman's fashion design. This causes problems, because:
These often do not pair well.
How to fix it.
You need to be a lot more selective when choosing garments. If pairing with menswear tops, look for skirts in stiff fabrics and muted colours.
If one is wearing a ruffly skirt, change out top garments to ones with ruffles and other details, as they will generally pair better.
Avoid strong colour contrasts, or learn about colour theory and how to combine colours within an outfit. Colour and pattern mixing are artforms in their own right.
Extremely baggy and unfitted top garments obscure body shape
Most menswear upper body garments are basically completely unfitted to the body. This hides and obscures the shape of the body. Skirts also do a great job of hiding the innate shape of the body. The combination then results in an outfit looking like a shapeless blob.
How to fix it
For an outfit to be flattering means that there is harmony between the individual garments in the outfit, as well as between the garments and the body.
Instead, pair skirts with fitted tops or tops with shaping in the side seams. This creates a 'small top, large bottom' contrast within the shape of an outfit.
Oversized garments can work if they are tucked in at the waistband and allowed to blouse. 'Blouse' besides meaning 'a woman's shirt', also means to puff. A shirt puffing out at the waist.
Oversized tops can also work if they are long and flared. This creates a 'dress over skirt' silhouette.
Closing notes: it is important to style outfits to work as a whole.
Men who try wearing a skirt for the first time often end up with outfits that look awkward, because they are not considering the balance of the whole outfit.
The majority of menswear garments available are designed to work harmoniously around an outfit using long trousers. While a long straight skirt can also pair well with menswear tops, most skirts do not.
Skirts and trousers read very differently when one views an outfit. Skirts push the viewer's eye to the silhouette of the outfit as a whole, if the proportions of that look bad, the whole outfit will.
Making skirt-based outfits look good on a male body generally requires changing everything one is wearing. Doing this will result in outfits that look distinct from common menswear, however they will not read as broken, weird, or stand out anywhere near as much as an outfit that was built haphazardly.