"I'd feel naked if I wore baggy pants," said Jonny, who lives in Marlowe, W.Va.
The teens are likely emulating the style of today's musicians - who are adopting the style of rockers from the '60s, '70s and early '80s, said Katherine Cooker, director of Shippensburg University's Fashion Archives and Museum.
"Hendrix wore tight pants. Mick Jagger will probably be buried in tight pants," Cooker said. "Have you not seen the gorgeous picture of Jim Morrison with no shirt and tight pants? That look is still buried in my memory."
While the idea of young people wanting to dress like rock stars isn't new, Cooker said seeing young men buy women's clothes is a new take on the trend.
"Before, it was the women who were buying the men's clothes," Cooker said.
Of the 17 men's rock groups within a recent top 50 of Billboard's Top 100, 11 had pictures on their Web sites of at least one band member wearing suspiciously tight britches.
As such, fall collections from high-end menswear designers have made skin-tight pants prominent. Several male models for Gucci sashayed down the catwalk in tight black leather pants during the label's fall runway show. A snug pair of men's Dolce & Gabbana jeans sell for around $325 at Neiman Marcus.
But for those who don't have that kind of money, women's jeans are the best alternative. Jonny said he shops at thrift shops for his ladies' jeans.
"Sometimes I go to discount stores," he said.
Large-scale retailers have seen men's jeans become narrower, said Amy Cafazzo, a spokeswoman for Marshalls.
"We are definitely buying narrower jeans for men," Cafazzo said. "It just isn't as cool to wear your pants so big and bulky."
Still, not everybody is a fan of the new trend.
"I think it's stupid," said Jen, the one who vowed never to date a guy who wears ladies' pants. "I think they're trying way too hard to be different, but really they aren't different because everybody is doing it."
Her friend and fellow classmate, Danielle Brunner, 14, said she only recently determined that she didn't like the look of guys in women's jeans.
"I used to date a guy who wore girl pants," she said.