"For me, [high-waisted] is a pretty easy go-to and I like the casualness of it," Jepsen said. "You can wear a colorful halter with it. You can wear any sort of crop-top thing and it feels really great for the summer festivals. You can dress it up or dress it down. If you want to do a blazer and a hat and heels or if you want to just go [with] Keds and rock it, it's an easy look."

But the path to being comfortable comes with some trial and error. Jepsen recounted a recent learning experience with some accessories that didn't quite work out.