Richard Chai recently picked up some Nike trainers in an attempt to jump-start his cardio regimen but liked wearing them around the studio so much that he ended up buying another pair just for workouts, and styled each Resort look with his favorite kicks.

Chai's Love collections often have a sportiness about them, and the latest lineup fused that athleticism with another tried-and-true Chai trope, boy-meets-girl dressing.

Slouchy striped silk pants were paired with a shaped, slim blazer, and one crinkled cotton utility vest looked, said the designer, "like she stole her boyfriend's army jacket and cut off the sleeves." On a side note, he loves breaking in new clothes and recommended washing items in a tub of salt water for well-worn appeal. Shuffling through the images, Chai pointed to look 10—a cropped jean jacket layered over a viscose tank with a shirt tied around the waist—and laughed, "I feel like that's the girl version of me." By Brittany Adams