Mirror, Mirror: Skirts and dresses for guys? 'It's all about expression'

Mickey Freeman, left, Mark Freeman, and Kyle Michael, right, display the androgyny look in Philadelphia. ( DAVID MAIALETTI / Staff Photographer )

Kyle Michael Upchurch wears skinny jeans, slim T's, cropped jackets, and shiny, wedged sneaks. Occasionally, he dons a tunic-and-leggings combo, too.

Now, the 22-year-old stylist at Century 21 is itching to add an additional splash of fashion-forward swag to his wardrobe by mixing in a few skirts - and dresses.

And before you ask, Upchurch said, he's not gay.

"I love women," he said emphatically, as he raised eyebrows tweezed into quarter moons. "I'm experimenting with my style. This is art to me. It's all about expression.

You don't have to walk too far in Center City to see that more young men are looking like they belong in women's Vogue. And they're not alone: They point to such male celebrities as Kanye West, A$AP Rocky, Justin Bieber, Jared Leto, and Jaden Smith as fashion soul mates. (Last month, Smith, son of Hollywood A-listers Will Smith and Jada Pinkett Smith, donned a floral-print dress at Coachella.)

For these men, it's not about cross-dressing (many of these clothes were designed for men), and not a reflection of their sex. Whether they are gay or straight or transgender or transcending - their sexuality is not what makes them choose skirts over suits.

Today, nobody would assume that a woman wears a pantsuit because she is a lesbian, but back in the 1920s, they might have. Experts say today's menswear trends could be the beginning of that same evolution.

"Gender is much more of a social category than a biological and sexual category with young people these days," said Nancy Hirschmann, director of the Alice Paul Center for Research on Women, Gender, and Sexuality at the University of Pennsylvania.

The men say they merely are free spirits, artists, if you will, who don't want to limit their clothing options to traditional and been-the-same-forever clothing: suits, ties, khakis, and polos.

"I wore this to New York Fashion Week, and I was mobbed," said 24-year-old Ricky Cantando, of Malvern, as he showed off the train of a spaghetti-strapped Rick Owens evening gown.

"But I do it in a masculine way," he said. "I don't wear makeup. I don't shave my legs. I'm not trying to be a woman. In fact, I really like being a guy. I just like the way this all looks."

Menswear has informed women's wear since the 1920s, when Chanel essentially created the suit. In the 1970s, Yves Saint Laurent introduced Le Smoking - the women's version of the tuxedo. And today, women in pants are almost more commonplace than women in red lipstick.

But, historically, men's fashion hasn't been nearly as receptive to women's wear. In the 1980s, David Bowie wore eyeliner, and Prince wore heels, but these looks rarely made it offstage.

Then, in the early 2000s, after Thom Browne started slimming down suits, Paris-based Rick Owens showed men the power of layering and turned the T-shirt into a knee-length tunic.

With each subsequent season came more gender-fluid lines aimed at men. Shayne Oliver's popular fall 2015 Hood by Air collection includes pleated dresses and tube skirts with thigh-high splits.

Dao-Yi Chow and Maxwell Osborne - both named creative directors at DKNY last month - put their models in ankle-length, palazzo-style pants paired with plaid tunics for their fall 2015 Public School runway show.

The trickle-down to mainstream fashion is serious business. Such labels as H&M and Zara sell menswear leggings, tunics, and even skirts for guys looking to soften their sartorial edge. According to the NPD Group, menswear continues to be the fastest-growing segment of apparel.

As further proof of pop culture's acceptance of women's wear-like menswear, look at our male celebrities - not only comfortable wearing skinnies and sheer sheaths, but also carrying man bags, rocking man buns, and wrapping themselves in infinity scarves on stage and Instagram.

Two weeks ago, Chanel released photos of its pre-fall 2015 campaign featuring model Cara Delevingne and Pharrell Williams. The latter sits, legs crossed, in a pair of knee-high, forest-green suede boots and layers of long necklaces, his cheeks contoured to perfection.

"When I saw Pharrell, I thought, why isn't he in a dress?" said 23-year-old Stephen Michael Quick of South Philadelphia, who wears thrift-store skirts. "You are the face of Chanel this season. Throw some drape in it."

Still, while artists, creatives, and those who support them embrace menswear's newfound freedom, others express disgust. On a recent sunny afternoon, Quick and Cantando walked along Eighth Street in skirts and were met with stares, glares, and head shakes, mostly from the men they passed.

"Clothing is one of the ways we signal our embodiment of cultural norms, and that's threatening to people," Hirschmann said. When someone such as Jaden Smith chooses a dress but says he isn't gay, those norms are then challenged on a worldwide stage.

These kinds of choices become even more critical in the black community, where seemingly any fashion choice can be judged negatively in the media, in their community, and at home: Hoodies are violent. Baggy jeans are lazy. Suits are uppity. Skirts are soft.

But thanks to such NBA players as Dwyane Wade and Russell Westbrook, people are becoming accustomed to less rigid notions of sexuality, said Mark Anthony Neal, a professor of African American studies at Duke University. In fact, he said, a more feminine, softer look is a way black men "can protect themselves from being targets."

"As black men, we are so restricted," Quick said. "Any fashion decision we make can get us killed, so we tend not to express ourselves. But that's harmful to us, too. Very harmful."

Sometimes, the reasons men wear women's clothing is quite simple. Ishmael Jaramillo of South Philadelphia wears women's Carmen Marc Valvo blazers over tween tanks because of his slight stature - he's barely 5 feet tall.

"Jackets are too broad, too long, and they just drag at the waist," the 22-year-old fashion design assistant said.

Cantando, who is gay, likes how he looks in wedges - the reason that, at 14, he convinced his mother to buy him a pair of Skechers. And 27-year-old Mark Freeman, of Bala Cynwyd, who describes himself as sexually ambiguous, wants to prove that rappers can spit lyrical fire in skirts. Upchurch, of West Philadelphia, points out that medieval men - such as the sword-wielding characters in HBO's Game of Thrones - and ancient Egyptians ruled empires in skirts and kilts.

They agree that it boils down to owning their identity.

"At the end of the day, I'm a man," said Mark Freeman's brother, Mickey Freeman, a gay, 29-year-old fashion stylist who typically wears leggings under skirts - in all black, of course - when styling clients.

"I open doors for women. I take care of my own. But I grew up in fashion, and it's about me being free to dress the way I want to dress."