Wes Hollywood is a beautiful conundrum.

He is at once a modern craftsman and a retro stylist, a purveyor of vintage rock songcraft whose stylish leather boots are planted firmly in the 21st century. Mr. Hollywood has been a staple in independent music for decades, first with The Wes Hollywood Show and then as tenniscourts. The names may change, but the sound remains a constant—two parts delirious Kinks melodicism mixed with one part Cheap Trick whipcrack, a splash of harmony and a bracing dash of fashion.