Sienna Spiro Wants You to Risk Getting Your Heart Broken

On a drizzling, humid afternoon in Chicago, I am nestled between hundreds of fans to get a glimpse of singer-songwriter Sienna Spiro’s magic at her first-ever Lollapalooza set. It was easily the most crowded performance I attended the whole weekend. Maybe the loudest, too. I was smushed between 20-somethings belting all the words to “You Stole the Show” in catharsis, like all of our exes were listening. When another fan sidled up beside me, she declared, “She should have been on a bigger stage.”Just four years ago, Sienna was attending music school in London when she posted a cover on TikTok and was discovered immediately. And this July, the 20-year-old’s first album, Visitor, debuted at number 9 on the Billboard 200. She’s landed three consecutive singles on the chart and has amassed more than 20 million monthly listeners on Spotify. It’s no wonder she’s already a strong contender for Best New Artist at the 2027 Grammys. When I mention that on Zoom, she says she “doesn’t want to jinx anything,” although her eyes light up.Part of the love for Sienna could be her style, a strong departure from the “clean girl aesthetic” taking over our feeds. In fact, that aesthetic makes her uncomfortable, she says while wearing a baggy t-shirt with her hair pulled back (compared to her usual ’60s beehive), but, of course, her signature winged liner is still drawn on her face despite the casual apparel. “One time, I bought an Etta James vinyl because I just loved her eyeliner,” she says. “I feel like eyeliner is always in. I don’t think that’s going anywhere.”Visitor, which explores themes of fear of abandonment, is filled with heart-wrenching confessionals that showcase her signature jazzy voice (she’s been compared to Nina Simone, Adele, and Nancy Sinatra, among other genre greats). It’s hard to believe she’s only 20 years old, with this visceral, raspy voice and strong presence. “When I record, I don’t do anything to my voice; it’s just me,” Sienna tells me. “When I’m in someone’s earbud, they probably feel closer to me, and they probably feel more.” But there’s an ineffable feeling when you’re watching her perform face-to-face, as I got to see at Lollapalooza and many others will on her sold-out worldwide My House Tour.After her Cosmo shoot (where she tried many of our Readers’ Choice Beauty Award winners), Sienna and I spoke about her takes on love and relationships right now, friendships, how she developed her personal style, and how she wrote her debut album.Jared KockaTop Carolina Herrera, briefs Kiki de Montparnasse, tights Emilio Cavallini, shoes Jimmy Choo, belt Deborah Drattell.On Visitor, you focus on impermanence and feeling like a visitor floating in and out of situations, particularly love. To me, this reads as a lot of situationships, which is precisely the dating landscape of today. People now, in this generation, are really afraid of love and afraid of being hurt and afraid of putting themselves out there to get shut down. I think that’s where this has come from. It’s for people who aren’t ready to fully commit. They want to see and then take a step back. And I think people are so afraid of being cringe. Everything is so much more broadcasted now, so there’s this other element of pressure.What are your thoughts on situationships? I don’t like them personally. I’m a very intense person. I am incredibly passionate and stubborn and enthusiastic, and I’m scared of getting hurt. Of course, I’ve been hurt so much in my life, but that is what this album has taught me: finding ways of looking at things.The last song on the album, Mono No Aware, was really a genuine turning point in my life, in my relationships, to stop putting a toe in and being like, Oh, do I like this? Is it going to be safe? I will lay myself out to dry. And if I get hurt, I’ll just pick myself back up and move on.But you’re going to regret so much in life that you haven’t done, rather than regretting the things you have done. You can learn from them. That’s what the song “Time, You & Me” is about, really.I am incredibly passionate and stubborn and enthusiastic, and I’m scared of getting hurt. —Sienna SpiroHow do you grapple with writing about love right now? I really struggle with writing about being in love, and I struggle with writing while I’m in something rather than having perspective on it. But, you know, a lot of the things I write about aren’t just romantic love. They’re friendship, they’re family, they’re life situations—I think those sometimes actually make me sadder than romantic love.What do your friends teach you about love? More than anything else, I think my friends have taught me how to love. Friendships teach you how to show up. They teach you what it means to not be cynical in love. Sometimes you get a bad one, and you have a friend that, unfortunately, you have to say goodbye to. But for the most part, you don’t enter a friendship being like, “Oh, this could end.” You’re like, “All right, my new friend. This is my friend forever now.” And I think that has taught me more about myself. I’m so grateful for my friendships—particularly the female friendships—I’ve had in my life that have stuck around. And there have been very few of them.You have such a strong personal style that evokes the ’60s. What inspired it? I would be lying if I said that this job doesn’t put you in a place where you have to figure out what it is that you want. But the ’60s style is just what I love. It makes me happy. It makes me feel good onstage. I love watching performances of girl groups from the ’60s, like the Shangri-Las, the Ronettes, the Supremes. I just love the way they move, the way they dress. When I put on outfits like that, I feel like I’m putting on another layer of myself that allows me to tap into something.Trends are cool. But I really feel like now, because we can see everything, we’re way too aware of what’s going on. People need to feel the liberty to dress how they really want. That’s something I love about the ’60s. There was so much character, so much personality. You didn’t have everyone wearing the same thing every day because that’s what they were seeing online. I really hope that that circles back.How does your personal style influence your music? I’m not a fashion girl. I’m a musician. I enjoy wearing clothes, but it does absolutely nothing to my music. My music is me, front and center. I think sometimes my music influences the way I dress. In terms of onstage, if I’m performing a song that is a ballad or if it’s more up-tempo, that might influence it. But my fashion will never influence my music.I’m not a fashion girl. I’m a musician. —Sienna SpiroYou started blowing up after posting covers on social media, which is the origin story of so many of today’s greats: Justin Bieber, Billie Eilish, and the like. Tell me about that time. I wanted to do this my entire life. I’ve been writing since I was 10. Being an artist, a singer, has just always been my dream and what I wanted to do in my life. But posting covers was never really in my head as the way it would happen. I just did it. I posted one video, and that’s how I found my manager, who’s my partner in everything.I sang covers all the time, and I still do. I learned how to sing through singing jazz songs, like a lot of Nina Simone, Billie Holiday, Ella Fitzgerald, Frank Sinatra. That’s how I learned to use my voice and how to sing.How did going to music school help with that training? I think it was one of the best things I’ve ever done with my life. I met Eddie, my keyboardist, who I have played basically every show with since I was 16. It taught me so many lessons. You usually have to fuck up in places where there are consequences, and in school, you can fuck up, and it’s within the walls of the school. I’m so grateful for everything that school gave me. You know, I wasn’t there for a long time, but yeah, it was great.You get really vulnerable on Visitor. Was that hard to channel? It comes naturally. I think the only song that I struggled with was “Pure” just because there were a lot of things in there that I had to admit to myself that I didn’t really want to. I didn’t even mean to put that out. I wrote that so I could write other songs. I was like, “I need to get this out so I can move on.” And I guess we came back to it, and I was like, “Maybe this is something I should share because it’s an important part of so many [people’s lives].” I wouldn’t have got half the songs if I didn’t write “Pure.” That was hard just because that was something I had to admit to myself.Were you trying to relate to people? When I write songs, I really try not to consider anything else other than just writing the song. I think that is the detriment of modern music. Being too aware of other people’s opinions, being too aware of other people, sometimes you’re not going to get the most authentic work to you—just because you’re considering other factors.You clearly love performing. How does it feel when other people are screaming the lyrics you wrote? It always makes me feel so connected to myself and connected to other people and so present. Just an indescribable feeling that I feel like such a tiny percentage of people in the world get to feel, and I feel so lucky to be part of that because it’s so weird. It actually makes me go back, because I’m like, Oh my god, how has this happened? I go back to when I first thought of, wrote, and recorded the song, and I’m like, How is this? How do you guys know it now? It was mine for so long, and it makes me trace back to where it all came from.Lead image: Coat Coach.Styled by Billie Rose Owen. Hair by John Novotny at OPUS Beauty. Makeup by Jenna Kuchera. Manicure by Honey at Exposure NY.