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By Christina Shanahan
Updated Apr 22, 2016 @ 10:00 am
Johan Sandberg

Just before Andra Day walked onstage to perform a give-you-chills duet mash-up with Ellie Goulding at this year's Grammys, she paused to confer with the most trusted member of her inner circle. "My father grabbed my hand and whispered, 'Sand, look around. Can you believe where we are?'" Day recalls. "My family has been supporting me for so long, which hasn't always been easy financially, so it's important that we take these moments to appreciate how far I've come."

Johan Sandberg

It's been a transformative year for the 31-year-old crooner. She was nominated for two Grammy awards: best R&B album for her début, Cheers to the Fall, and best R&B performance for her smash single, "Rise Up." As "Rise Up" climbed the charts, her retro-inspired rockabilly aesthetic grew its own fashion following. Makeup-free, with her hair tossed into a loose, just-out-of-the-shower bun, Day is barely recognizable without her signature Hepburnesque coif and crimson lips. On a Lower Manhattan photo set, she indulges her penchant for bold florals and PJ-inspired silhouettes as she tries on a loose-fitting Dolce & Gabbana top and bottom set. "If it looks like your grandma's bedsheets, I'll put it on my body," she jokes. "What I wear onstage is so stylized and bold. When I'm not working, I still love bright colors and patterns, but I choose pieces that are much more casual—I call it my lazy pinup look."

Her shopping strategy, though, is the exact opposite of lazy. "I search for items that have history, like vintage finds—I love fur kitten-heel house slippers from the 1950s—and pieces from fashion houses that have been around for a long time, like Chanel and Dior." Fittingly, Day counts Lucille Ball among her biggest icons. "But not just because of her style," she says adamantly. "I admire her strong character and her charisma. She dealt with criticism over her marriage to Desi Arnaz, and she was the first actress to show pregnancy on TV."

Johan Sandberg

Day's thoughtful demeanor is a testament to how she maintains balance in her life as her career skyrockets (she joined the ranks of Sandra Bernhard and Bette Midler in Marc Jacobs's iconic spring campaign, kicked off a world tour, and has a film project in the works). "The key to being on trend is simply being content. When I'm feeling comfortable onstage, I'm giving my audience the best possible performance that I can," Day says. "As Iris Apfel said, 'It's better to be happy than well-dressed.'"