hris Kasper certainly looks the part of a troubadour, with a flower-adorned Homburg pressed over his chestnut locks and bearded visage, and an acoustic guitar slung over his shoulder. The songs on his most recent album, the wryly titled “O, the Fool,” reflect a classic troubadour’s restlessness too: perpetual cross-country searching despite inward doubts, expressed with a strong rhythmic sensibility.

Credit that intuitive feel for grooves to some jamband ventures in the early ’00s that followed his late-’90s adventures at West Virginia U. The Philly native sometimes gets tagged as an acoustic soulman, a rep that started following him around after he’d logged a lot of road miles playing coffeehouses, clubs and small festivals, and opening for better-known peers such as the Avett Brothers, Amos Lee, G. Love, and the Wood Brothers. (In 2015 he also collaborated with Philly’s BalletX troupe, which choreographed pieces to songs from his 2013 album “Bagabones” — a typically game creative experiment.)

Kasper’s lightly burred baritone tonally resembles Lee’s, and like him he makes music with a determined romantic streak and has ventured progressively deeper into Americana. On last year’s “O, the Fool,” piano and horns imbue “City By the Sea” with a speakeasy vibe, like dreams of old briefly stirred to life, and fellow Philadelphian Kiley Ryan’s violin and sweet harmonies add dusky tension and Appalachian feel to “Blood Moon” and a pulsing cover of Bruce Springsteen’s “State Trooper.”

It’s an interesting contrast to Kasper’s 2006 debut, “Flyboy.” By that point he was already a known entity in Philadelphia’s renowned folk community, but he was still developing his own sound. Listen to a show recording from that year, “Live at Maxwell’s,” and you hear an earnest musician starting to forge connections with an audience, augmenting his folk-pop originals with a choogling cover of Bob Dylan’s “Tangled Up in Blue.”

His new songs are more knowing. “Love Letter From Santa Fe” feels like a winsome sequel to “One False Move” from his 2009 album “Chasing Another Sundown,” in which he vowed, “I’m gonna sleep in Santa Fe.” Here, “in the Santa Fe sun with the birds flying over the shadows” while “living off cans of nothing,” he’s still longing for a morning with his lover but mining pleasure from the moment. That poetic, make-the-best-of-it attitude and his tasteful fretwork buoy the whole album.

“I followed all the signs they told me to believe/ And now I’m stuck in the desert with all that I wanted to see,” he notes in the string-cossetted “Wrong Way,” one of several songs that suggest a man mapping out myriad roads taken to determine if he’s where he should be or only the destination he’d dreamed of reaching. It’s a rich distinction to ponder, and Kasper does so compellingly. n

Chris Kasper and Kiley Ryan perform at the Wine & Song series outdoors on the patio at Arroyo Seco Golf Course, 1055 Lohman Lane, South Pasadena, at 7 p.m. Wednesday, May 16; $15. John Paul O’Connor also on the bill. chriskasper.com, blueguitar.club