Menswear Skirts

Skirting Stereotypes: The Rising Trend of Menswear Skirts (Plus How to Style Them!)

Brittny Drye Founder + Editor-in-Chief of Love Inc. Magazine | On-Air Wedding Expert | LGBTQ+ Inclusivity in the Wedding Industry

With menswear skirts now a staple on the red carpet, expect to see them to soon be entering the aisle. 

If you’ve been paying attention to red carpet events lately, you’ve probably noticed a growing trend: formal menswear and suits paired with skirts. And no, this isn’t some fleeting fashion experiment; it’s a full-blown movement that’s challenging the status quo and shaking up the fashion world in the best way possible, and we are so here for it.

Menswear Skirts
LOS ANGELES, CA – SEPTEMBER 19: Daniel Levy arrives on the red carpet for the 73rd Annual Emmy Awards taking place at LA Live on Sunday, Sept. 19, 2021 in Los Angeles, CA. (Jay L. Clendenin of Getty Images)

But First, A Brief History Lesson

Before we dive into the latest red carpet looks, let’s rewind a bit. Skirts have actually been a part of men’s fashion for thousands of years. Think about the ancient Greeks and Romans, who wore flowing tunics and togas. Or the Scottish kilt, which is still a symbol of pride and heritage. For much of history, skirts and similar garments were pretty unisex. It wasn’t until relatively recently—think the last couple of centuries—that pants became the standard for men, and skirts got “assigned” to women’s wardrobes.

So, in a way, this “new” trend of men in skirts is actually a return to our fashion roots.

Breaking the Mold: Why Men Are Now Choosing Skirts

So, what’s driving this trend? It’s not just about making a statement (though that’s definitely part of it). The shift towards skirts is also about comfort, freedom, and expression. For many, skirts offer a way to break free from the rigid expectations of traditional men’s fashion. Tuxedos and suits, while classic, can feel like a uniform—one that’s often more about blending in than standing out.

Enter the skirt: a garment that’s as versatile as it is bold. Whether it’s paired with a tailored blazer or a casual T-shirt, a skirt can be anything you want it to be. And on the red carpet (or, for our purposes, the aisle), a skirt is a guaranteed way to turn heads. “I make skirt suits to change the perception of men, to engage our thinking. What defines us?  Is it what we think people will say or how we feel about our inherent sense of knowing who and what we are in this limited lifespan,” says designer Terry Singh, whose menswear collections revolve around the skirted look.

But there’s more to it than just fashion. It is also about challenging gender norms and expanding the definition of masculinity, and, well, the need for even gendering attire in the first place.

Menswear Skirts
MILAN, ITALY – FEBRUARY 24: A$AP Rocky arrives at the Gucci show during Milan Fashion Week Fall/Winter 2023/24 on February 24, 2023 in Milan, Italy. (Photo by Vittorio Zunino Celotto/Getty Images for Gucci)

The Trailblazers: Celebrities Leading the Skirt Revolution

Let’s give credit where it’s due. This trend didn’t just appear out of nowhere—some fashionable celebrities have been leading the charge, making skirts a regular fixture.

Take Billy Porter, for example. The Pose star has become synonymous with breaking gender norms in fashion, and his looks are nothing short of iconic. Remember the 2019 Oscars? Porter showed up in a custom Christian Siriano tuxedo gown—a look that was half suit, half ballgown, and all fabulous. That moment wasn’t just about making a splash; it was a statement about the fluidity of gender in fashion. Since then, Porter has continued to push boundaries, proving that skirts (and dresses) can be powerful, no matter who is wearing it.

Then there’s Harry Styles, the pop sensation who’s been redefining masculinity for a new generation. Styles has made skirts and dresses a staple in his wardrobe, both on stage and at high-profile events. At the 2020 Vogue cover shoot, Styles wore a Gucci dress, sparking conversations about what men “should” wear. His willingness to embrace traditionally feminine fashion elements has made him a style icon for those who believe in breaking down gender barriers.

We can’t forget about actors like Jared Leto and Ezra Miller, either. Both have rocked skirts and dresses on the red carpet, each bringing their unique flair to the trend. Leto, known for his eclectic style, often pairs his skirts with bold accessories and statement pieces, while Miller leans into a more androgynous, avant-garde aesthetic. These celebs aren’t just following trends—they’re setting them.

Menswear Skirts
LONDON, ENGLAND – MARCH 17: Oscar Isaac attends the “Moon Knight” premiere at The British Museum on March 17, 2022 in London, England. (Photo by Karwai Tang/WireImage)

Designers Who Are Embracing the Skirt

Of course, none of this would be possible without the designers who are pushing the boundaries of fashion. Brands like Thom Browne, Off-White, Jil Sander, and Givenchy have been at the forefront of this movement, creating skirts specifically in their menswear collections. Even retailers such as ASOS and Adidas have jumped on the genderless skirt train. 

Thom Browne, in particular, has been a major advocate for men in skirts. His designs often feature structured, tailored skirts that blur the line between masculine and feminine. Browne has said that he sees no reason why skirts can’t be a part of men’s wardrobes, and his runway shows reflect that belief. His influence can be seen on red carpets and fashion runways alike, where more and more men are choosing skirts as a bold fashion statement.

If you're feeling inspired and wanting to rock a skirt for your wedding day, follow this style advice:

Here are five styling tips for men wearing skirts that combine confidence, comfort, and modern fashion:

1. Play with proportions and layers. Mix and match with proportions and layers, such as a tailored blazer, vest or pants underneath. A layered look not only elevates the outfit but can also balance the overall appearance, making it approachable and stylish.

2. Don't feel like you have to masc a skirt up with accessories if that's not your genuine style. “At first, I thought I needed military boots to man it up,” says designer Terry Singh of when he first started wearing skirts. “But after a few years, I realized that was a serving belief that was not true.”

3. Accessorize thoughtfully. Accessories like belts, hats, and statement jewelry can elevate the look and add personality. A belt, for instance, can help define the waist and add structure. Choose accessories that resonate with your personal style, whether that’s minimalist or bold.

4. Experiment with fabrics and prints. Don’t shy away from experimenting with different fabrics like leather, denim, or pleats, and prints like plaid, stripes, or florals. Yes, even for your wedding day. Today's wedding fashion is all about being an elevated version of yourself and your own personal style. Mixing textures and patterns can add interest and make the outfit feel more intentional and put together.

“Break away from ordinary, come into the new with a freedom of self-acknowledgment and knowing that everything you do now is new, starting with you. Dress for it!”

Cover photo courtesy of Terry Singh

This originally was featured in our V9 print issue. Grab your copy here.

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