In today’s installment of “Dear God, why??? Haven’t we been through enough this year?” I regret to inform you: The mid-aughts trend of wearing skirts over pants, for no discernible reason other than “style,” is back.
OK, it’s not really that bad. Sure, the idea may recall images of Ashley Tisdale’s much-memed 2007 red carpet looks. But the new iteration is much sleeker; the trousers are tailored, the skirts more form-fitting. Believe it or not, the combination isn’t all that bad.
Models for Proenza Schouler’s recent runway, which took place on Little Island, layered vivid orange sheaths over black cigarette pants. It looked put-together, but not constricting; the designers told Vogue they meant to celebrate movement, the idea of women being back “on-the-go” in their post-vaccine lives.
Thom Browne’s avant-garde take on the trend might not have been all that wearable—I doubt we’ll see pinstriped poncho tent dresses over slacks everywhere come spring, though stranger things have happened. Still, the androgynous styling felt modern and courageous. It had a theatrical flare, and something that wouldn’t be unimaginable for someone like Billy Porter or Dan Levy to wear on the red carpet this season.
They’ll be following in the footsteps of Queen Latifah, who already wore a Thom Browne skirt/pantsuit to the BET Awards in June. She put on the look to accept a well-deserved Lifetime Achievement Award, and toted a small briefcase. The strict, schoolmarm-ish tailoring had a little whimsy to it. It was the perfect cosplay of “professionalism,” a nod to that old-school type of power dressing that’s practically gone extinct thanks to Zoom.
Skirts over pants, generally, are a great example of anti-Zoom fashion; you have to be out to show it off. “I think a skirt over a pants is a way to make a skirt or dress feel a little more relaxed and less prissy, not to mention a cool proportion play,” Véronique Hyland, the fashion features director at ELLE and author of the upcoming essay collection Dress Code, told The Daily Beast. “There may also be a conscious or unconscious ’90s and ’00s reference, as those eras have been popping up so much lately. Depending on how you style it, there can be a grunge influence or a pop-punk influence.”
It’s true: someone’s reference point for what skirts over pants mean depends on how old they are. Gen X knows the trend from the early days of MTV, when it was subversive and dangerous. Think of maximalist Madonna, throwing a miniskirt over textured leggings, becoming one of the prime evangelists of that look.
There are a few prototypes, though. As Julia Brucculieri of the Huffington Post has noted, it can be seen in certain cultures’ traditional dress—for both men and women. There is the kurta or kurti in India, which is a tunic over trousers and can be worn both casually and formally. The áo dài, from Vietnam, is a gown with trousers typically reserved for a special occasion.
The first time women in the West were allowed to wear pants en masse were with the advent of bloomers, named after newspaper editor Amelia Bloomer. She managed the first women’s newspaper, The Lily, and in 1849 aligned the “Turkish” pantaloons over a shorter skirt with women’s physicality—and therefore rights.
“As soon as it became known that I was wearing the new dress, letters came pouring in upon me by hundreds from women all over the country making inquiries about the dress and asking for patterns—showing how ready and anxious women were to throw off the burden of long, heavy skirts,” Bloomer wrote. The suffragette Elizabeth Cady Stanton loved the look, saying it made her feel “like a captive set free from his ball and chain.”
Bloomers freed women from perilous hemlines and hefty hoop skirts. But today’s skirts-over-pants look can restrict mobility.
“When it comes down to it, there’s no utility reason to wear a skirt when already wearing pants and vice versa, meaning that when you do so it is a conscious stylistic choice,” said Yoona Bang, a 19-year-old student and freelance stylist who lives in Dallas. “It’s just so bad it’s good. I love how it can warrant both positive and negative reactions—it makes me feel like I’m doing something right in the way I choose to dress.”
Bang says her favorite take on the look “is the iconic Ashley Tisdale at the 2005 premiere of Ice Princess.” Tisdale’s more-is-more mid-aughts outfits have been the subject of much internet adulation; at this specific event the then-18-year-old wore a Bebe top blazed with the word “DREAM,” faded bell bottoms, and a metallic skater skirt. All at once. She even toted a keytar-shaped clutch for good measure.
The wardrobe resembles what a toddler might wear if allowed to run rampant in their mom’s “going out” clothes. Which is, actually, a great descriptor for high fashion as an overall aesthetic.
“There’s a certain shock factor to that particular outfit that I truly believe the modern-day forms of minimal skirts-over-pants looks couldn’t exist without,” Yoon said.
She’s got a point. One outfit from Peter Do’s spring collection may have been more refined, but it certainly hinted at Tisdale glamour. A model wore oversized jeans, sandals, and a large white button-up shirtdress that had been artfully embellished. It was a bit of a grown up mid-2000s vibe.
So why is the look divisive? “I think people hate it so much because it forces us to feel something,” Yoon said. “It’s such a bizarre combo that was never meant to go together so it can easily feel ‘wrong,’ but I think there’s an artistic beauty and charm in that.”
One also must take a solid stance against “coolness” to pull off this admittedly dorky trend. “I think a lot of people aren’t big fans of returning Y2K trends,” said Layal, an 18-year-old fashion student from Saudi Arabia who did not give her last name. “People see skirts and pants and think it’s the ugliest combination ever. I’m not going to lie and say I love all the old takes on the trend, but the modern rendition of it really takes my heart.”
“People are afraid of experimenting,” Rachel Rubí, a 23-year-old graphic designer from Miami said. “I remember celebrities playing with skirts over pants in the 2000s and many people absolutely hating it. But I think in 2021, people are finally waking up to the fact that life is more fun when you don’t restrict creativity.”
Or as Bang put it, “If more people could overlook their initial gut reaction to hate [the look], then society could be a much cooler, skirt-over-pants filled place. S.O.P. supremacy!”