Singer-songwriter Hailey Whitters brought a little country flair to New York City’s Hammerstein Ballroom earlier in November, opening the venue for country trio Midland. Rolling Stone News caught up with Whitters on her tour bus before the show, where she discussed her plethora of D.I.Y. crafts, her country fashion inspiration, and her relentless optimism.
Whitters’ colorful tour bus is, as she puts it, “inspired by some of my favorite dive bars, some of my favorite honky-tonks. It’s our little honky-tonk on wheels.” Whitters, wearing a “Corn is for lovers” T-shirt that’s available from her merch store, also has colorful string lights and even a quilt that was made by her grandmother for her father.
Along with her T-shirt celebrating the big crop of her native Iowa, Whitters’ onstage style tends toward the bold and colorful with a nod toward country icon Dolly Parton. “She never took anything too seriously,” Whitters says, noting that she generally sticks to comfort wear when she’s offstage.
Whitters also dug into some of the lyrics on her 2020 album The Dream, explaining the themes of hope and perseverance that course through songs like “Glad to Be Here” and “The Ride.” “I’m an optimist to a fault, even when it’s probably not smart to be an optimist,” she says. “I’ve been through some shit, I’m sure we all have. I always try and look at the bright side.”
That’s hard-won optimism in Whitters’ case — nearly 14 years ago, she came to Nashville as a naïve 17-year-old and had to figure out how to stay afloat. She touched on that arduous journey in her song “Ten Year Town,” explaining to Rolling Stone that those ebbs and flows aren’t that far in the past.
“It’s constantly been highs and lows for me, and learning to roll with it,” Whitters says. “How to navigate and move and find perseverance to hang in there and keep going.”