How To Dress Masculinely in a Skirt: Part 1

In this article, I’m going to give a few tips and examples of how to dress in a more masculine way while wearing a typically feminine garment: the skirt. Dressing masculinely in a skirt may seem like a paradox to some, but it is absolutely possible.

Not every man who regularly incorporates skirts into his wardrobe will want to look masculine all the time or even at all. That is perfectly fine. However, some men, like myself, wear them simply because they like them and also to express a certain level of femininity without wanting to entirely mask his masculinity. For those men, skirts are more of a feminine ornament to accompany your mostly masculine style.

Choosing the Right Skirt

Dressing masculinely in a skirt starts with choosing the right skirt. There are a variety of different types of skirts to choose from and each man will look good in some types, but not others. That, of course, makes it impossible to say exactly which type of skirt you should choose to look “manly”, but I can at least give some advice for the different types.

I won’t go into all the different types (there are a lot!), but I will mention a few here that generally look more masculine. In the end, it comes down to what you’re comfortable in and what you think looks good and fits your body type.

If you are going for a more masculine look, then there are a couple of things that should be said about all types of skirts. Generally, you should avoid skirts with an abundance of “feminine” features such as lace and bows. Floral patterns should also be kept to a minimum and instead bold colors should be chosen. The cut is also important with more angular, less flowing cuts appearing more masculine.

Again, that is a matter of opinion and since we are already questioning what it means to be “masculine” by wearing skirts in the first place, then it would be correct to question the validity of those tips as well. That said, we are going to focus on what is generally still considered masculine by the majority and thus what will make you appear more so to the untrained eye.

Kilts

Let’s start with the obvious. Angular cuts, a long heritage of men wearing them and bold colors: the kilt is the definition of a man-skirt. It is also the most socially acceptable way for a man to wear a skirt in public. Sure, he may get a few odd looks, but nothing like if you were wearing a short, leather mini skirt.

The kilt is the obvious go-to for any man who is looking to dip his toes into skirt-infested waters without kicking up too much of a stink. There is a huge variety of cuts, patterns and even materials which means that every man should be able to find something he likes.

Pleated and Box Pleats

Pleated skirts, particularly those with box pleats, are the kilt’s cousins. Most kilts have pleats, so it makes sense to take a look at other pleated skirts first.

We’ll start with skirts with box pleats. These are often so similar to kilts that a man can easily get away with wearing them in public since people will assume it is just a kilt. That is particularly true if they have a tartan pattern. These are a great choice for men wanting to have a slightly more feminine skirt than a typical kilt, but still want a more masculine look.

Other pleated skirts are quite feminine though. These tend to be longer and often have a silky/shiny material. While they are comfortable, are fun to wear and look great, they are best avoided if you are going for a masculine look.

The pitfall of pleated skirts (with or without box pleats) is that they are often quite short. These are great for hot weather, but generally don’t look particularly masculine. I’m getting ahead of myself though. I’ll cover skirt length in a little bit.

A-Line

A-line skirts are my personal favorite. They are comfortable, fun to wear and come in a huge variety of colors, patterns, styles and lengths. For me, they are the perfect combination of masculine and feminine as they are vaguely kilt-like, but have much softer lines.

For a more masculine look, I choose solid, bold colors and a skirt that isn’t too tight or short. A-line skirts are more flowy than pleated skirts and kilts which also makes them appear more feminine. They also, as the name implies, flow outwards from your thighs, giving the wearing more of an A-like shape.

Pencil and Straight

Pencil skirts are great for a more formal look. They go well with suit jackets and ties and generally make the wearer appear more serious and sophisticated. Several men, including Mark Bryan, rock a pencil skirt and make it look very masculine indeed.

However, they do tend to be a lot tighter than other types of skirts which means that certain parts of a man’s lower anatomy that our female counterparts don’t have tend to bulge outward if you don’t pay attention.

Wrap

As the name implies, these skirts wrap around the body and are fastened by a button or clip rather than slipped on. The most masculine type of wrap skirt is the kilt and any sort of tartan-patterned wrap skirt could easily be mistaken by the untrained eye as a kilt – perfect for going incognito if you want to wear a more feminine skirt, but don’t want to stand out too much.

As a bonus, the way they wrap around the lower body also makes using urinals possible which is not something you can typically do with other types of skirts.

Sarong

The sarong is another type of wrap skirt that is traditionally worn by both men and women in many African and Asian countries. These skirts tend to be brightly colored with busy patterns which mean they aren’t subtle.

While they are traditionally worn by any gender in some cultures, they will still stand out in Western cultures, especially due to their bold appearance.

Other Types of Skirts

As I mentioned above, there are a lot of different types of skirts. Those I covered above are, in my opinion, the options that will give you the most masculine appearance. Of course, others may disagree and that is perfectly fine. I enjoy wearing other types of skirts as well, but I am also not always going for a particularly masculine appearance.

Below is a reference for a few more types. Note that the kilt is not included in this graphic.

Skirt Length

The length of a skirt can be a highly objective topic and depends a lot on personal style. What looks good on you will also depend on your body type, but I am not going to go into detail on that matter right now. My focus here will instead be on what skirt length gives you the most masculine appearance to the casual observer.

If you are going for a more masculine look, then a mid-length to maxi skirt will suit you best. As I have done several times throughout this article, I am leaning on the appearance of skirts typically associated with men – such as kilts and sarongs – as well as current trends in men’s fashion to inform my opinion.

Kilts tend to be about knee-length which puts them firmly in the mid-length range. Maxi skirts are great for the winter and could be associated with the sarong which also makes them a great choice. Just keep in mind, however, that they have the potential to look somewhat less masculine in Western cultures since maxi skirts are often associated with women in previous eras. Just think of the typical Victorian/Edwardian woman.

Current men’s fashion does not include short shorts or much of anything far above the knee which means a mini skirt will look less masculine and out of place. That doesn’t mean a man can’t wear them if he is going for a more feminine look, but to the untrained eye, it won’t appear as masculine as a longer skirt would.

Conclusion

Since this post is getting quite long, I have decided to divide it into two parts. The second part will be published in the near future and will be linked below once it is finished. It will feature advice about choosing the right shirt to go with your skirt as well as other accessories and what to wear under your skirt.

In the meantime, I suggest you take a look at the Pinterest board shown below. There are a huge number of ways to style skirts in a way that looks very masculine and that board has a lot of inspiring images with a variety of different styles.

How do you style your skirts? Do you dress in a more masculine or feminine way? Or do you switch between them? Are there any tips you want to share? Let me know in the comments below!

This article continues in Part 2.

Inspiration

If you are looking for more inspiration, take a look at this Pinterest board: