John Craigie learned an important lesson while on his first U.K. tour earlier this year. It involved his pants.

"In the U.K., they speak English, but it's different—their word for pants is 'trousers,' and 'pants' means 'underwear,'" says the 37-year-old Portland-based singer-songwriter. "I wear bellbottoms, and I like embroidered stuff. Lately, I've been finding that I have to buy women's pants because they just don't make men's pants like that anymore. I was onstage, it was my first show and someone yelled out, 'Nice bellbottoms!' I said, 'Yeah, I only wear ladies' pants.' Everyone got really uncomfortable. Someone told me after the show, 'That means you're wearing ladies' underwear.'"

As mildly embarrassing as that story is, that's the kind of interaction Craigie prefers to have with his audience, and he likes to keep his shows small and intimate enough for it to happen. But that might not be possible for much longer. He spent the summer touring with Jack Johnson, and his latest record, No Rain, No Rose, is his most successful yet.

It was probably inevitable that Craigie would eventually find a bigger audience. His music is in the lineage of classic folk singers like John Prine and Arlo Guthrie, with a focus on melodic storytelling. He has a deep, soothing voice, and an appealing songwriting style that's at once poetic and hilarious. See his song "Naked Skype," an examination of modern dating rituals.

No Rain, No Rose is a tribute to Portland, where he moved to from California two years ago. The title plays off a Buddhist saying, "no mud, no lotus," which Craigie altered to "make it more appropriate for the Northwest." He recorded in his Southeast Portland living room, in front of his friends, and you can hear their commentary and conversations between tracks.

"I don't really like recording," Craigie says. "It feels lame and forced. I like having an audience there that I can play off of and talk between the songs. Having all of them there let me do just that. It couldn't have worked out better—having an album about that new community in Portland and then having them all be there for the recording."

Craigie is looking to release two records within the next six months. Appropriately, one of them will be a live recording. As for No Rain, No Rose, while happy with it, Craigie makes sure to keep his pride in check.

"Never trust a musician who is too stoked on their new record," he says.

SEE IT: John Craigie plays Mississippi Studios, 3939 N Mississippi Ave., with Hollis Peach, on Thursday, Dec. 7. 8 pm. Sold out. 21+. He also plays Doug Fir Lounge, 830 E Burnside St., on Friday, Dec. 8. 9 pm. Sold out. 21+.