How To Dress Masculinely in a Skirt: Part 2

Continued from Part 1.

In the first part of this guide, we focused on which styles and lengths of skirts appear most masculine to the average person who isn’t used to seeing men wear skirts. In part two, we will explore what types of patterns you should choose for a masculine look as well as shirts, shoes and accessories.

Skirt Patterns

The pattern on your skirt is at least, if not more, important than its cut when it comes to appearing feminine or masculine. It goes without saying that floral or lacy patterns won’t appear particularly masculine. While that isn’t to say that men couldn’t or shouldn’t pull off a lacy or flowery look, you might want to choose a different pattern if you are wanting a more typical manly look.

As with the cut, rougher, more boxy patterns will appear more masculine. You can never go wrong with a tartan or checkered pattern, for example, even if you aren’t wearing a kilt. Just think of how most men’s shirts look when you look at them in a clothing store. There are racks upon racks of checkered, button-down shirts.

If tartan or checkers aren’t your cup of tea, then I would go for a solid color. Bold colors are preferable with darker ones being more subtle than bright ones. A black or dark green, blue or red skirt will serve the purpose much better than a pastel color. If you want to stand out, then a bright color will also work wonderfully. The only more pastel colors I might go with would be khaki or gray.

Choosing the Right Shirt

Choosing the right shirt is also important for creating a masculine look while wearing a skirt. This one will be easy for most men as it mainly involves picking out a shirt they already have in their closet.

Any male shirt will work as long as it looks good with the skirt. You just have to consider your shirt selection in the same way you would when picking one out to go with a pair of pants. Does the color fit? Does the pattern clash?

Shirts that work best for a particularly masculine look are polo shirts, Oxford shirts or t-shirts. The important thing is that they are cut for a man’s body and would be something you would wear with a regular pair of pants.

Shoes

Choosing shoes to go with a skirt can be a more delicate task than picking a shirt when going for a more masculine appearance. Not all men’s shoes, for example leather dress shoes, pair well with a skirt, so you need to choose wisely.

Which shoes you pick will depend on the style you are going for. Combat boots with high socks make you look very masculine and evoke images of kilt-wearing warriors. They work well in any season, although can be a little warm in the summer.

Otherwise, low-topped shoes such as Vans or Converses worn with ankle socks or sandals are great for warm weather. Essentially, you can wear anything you would wear with your normal man-shorts, although tennis shoes might not be the greatest choice either.

For colder weather, it highly depends on what you have on under your skirt. If you are wearing a pair of jeans or leggings, then choosing shoes that pair well with those is the best way to go.

A lot of men who wear skirts often complement them with high heels. Some wear sandals, others wear pumps, while others wear heeled boots. They can all look great and can go very well with a skirt, but should generally be avoided when trying to look more masculine. Of course, low heeled boots such as biker boots or cowboy boots can be an exception if that is the style you are going for.

Other Accessories

As with pants, accessories can make an outfit with a skirt much more complete. Little details such as the size of your watch or style of a bracelet or necklace can entirely change whether an outfit is masculine or feminine.

Watches and Jewelry 

As I have mentioned in previous sections already, men’s fashion tends to be blockier, bigger and clunkier than women’s. That means when choosing a watch, you should go for something large and bulky to really emphasize your masculinity.

The same can be said about other jewelry such as necklaces and bracelets. While leaving them out entirely is certainly a very masculine thing to do, you should choose “rougher” looking jewelry such as those with leather bands if you want to include them. They will help counter the feminizing effect the skirt has to the untrained eye.

Jackets

Of course watches and jewelry aren’t the other options for accessorizing. Jackets are always an option, especially in cold weather. 

A sport coat or blazer does wonders in making an outfit look not only sleek, but also in showing off your maleness. That is especially true if it is well cut to emphasize male shoulders.

For more casual occasions, a leather jacket is another great option, particularly if it looks rugged and worn or gives off a certain tough, biker-like attitude. While that might seem contradictory to what our goals are here, combined with a skirt, it will soften the look of the jacket while preserving the masculineness of it. 

What to Wear Underneath

Any man who has ever worn a kilt out in public has been asked the dreaded question: do you have anything on underneath? If it isn’t obvious, then like with women, it’s nobody else’s business.

While what you wear under your skirt is largely irrelevant in summer and should be left to the individual man to decide on what sort of undergarment, if any, he would like to don, it becomes more interesting in winter when you will most likely wear something longer underneath that will be visible below the hem.

There are many options available to skirt-wearers, but not all of them look masculine. Pantyhose, for example, is often worn under skirts, but looks very feminine. When going for a masculine look, you will, like I have mentioned before, want to go with something a bit rougher.

Woolen or cotton leggings are a great choice. Woolen leggings are rough and look very masculine whereas cotton leggings are more subtle and, when worn in a dark color, tend to disappear in the person’s field of vision. Choosing solid, darker colors is your best option for making leggings look masculine, although light grays also work well.

Another option is to wear your skirt with a pair of jeans. Now, before you butcher me for suggesting that, picture a man wearing a black skirt with a pair of black skinny jeans. It works and looks very masculine. If you do choose jeans, you will have to be very selective about the combination of skirt and jeans, however. A pair of Wrangers may not be the best choice to wear with a pencil skirt, for example. I would largely stick to dark skinny jeans as they look a little more like rough leggings.

Conclusion

When I had the idea for this article, I browsed the Pinterest board linked below for inspiration and I was pleasantly surprised to see that it really isn’t all that difficult to style a skirt in a masculine way. 

I really do suggest you take a look yourself. It’s very inspiring. There are tons of different examples of how to do it that encompass a large range of styles. Styles vary from man to man, so it isn’t possible to write an article that will speak to everyone, but there are enough men out there wearing skirts and posting pictures on the internet that everyone can find inspiration.

But of course, not every man is trying to look masculine in a skirt. Some are more heavily bracing the feminine look even if they aren’t necessarily trying to crossdress. There is absolutely nothing wrong with that either and I will probably even write an article about it as well.

Image Gallery

The pictures below are just a few of many I have found online that demonstrate how easy it is to dress masculinely in a skirt. Hopefully the also serve as inspiration to help you develop your own style.

Further Examples

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

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!