Kelsey Wilson has never been able to escape the pull of music. At the early age of 4, she began playing violin and quickly became fascinated with her family’s expansive record collection. Growing up homeschooled with a mother whose life had been embedded in the gospel church, Wilson found herself immersed in the genre and became enamored with R&B and gospel artists like Otis Redding, Billy Preston, Aretha Franklin and Nina Simone. It wasn’t until her teenage years that she was introduced to genres like country rap and pop. “None of it really hit after so many years of what I was listening to, so I just implanted gospel into my brain.” 

While Wilson never thought she would be a professional musician, life had other plans. In the early 2010s, Wilson found momentum as the lead vocalist and violinist of the Austin-based Americana outfit Wild Child. “I was writing songs with someone who played the ukulele, so I realized that I could fit melodies and words over the chords he was playing and it was really easy.” Throughout their 14-year tenure, the group released five albums and has toured with artists like Mt. Joy, Robert Ellis and Shakey Graves. Because it was “easy,” Wilson believed that she was supposed to be making folk music. After all, the band has found moderate success over the years, from movie and TV show placements to commercial jingles. But the music didn’t feel “authentic” to Wilson. “I wasn't being my genuine self,” she says. Still, she didn’t know what kind of music she would make if she was in complete control. In 2018, the year before lockdown, she penned what would be the first Sir Woman record — several songs that didn’t quite fit in the Wild Child world. At the time, she didn’t intend to create a band or touring the record. “I just wanted to make an album that sounded like me entirely.”

The name of Wilson’s rollicking solo project fittingly came to her just as Wild Child was playing the last festival before their hiatus. While roaming around the festival grounds, a security guard yelled at her, calling her “sir” and “woman.” Something clicked: It was the song that she had been singing in a dream the night before, the character she longed to create. “It felt so appropriate and reminded me of Motown, just classic but powerful. It was everything that I didn't really get to express in Wild Child.” 

As Sir Woman, Wilson took the Austin music scene by storm in 2022 with the release of her full-length self-titled debut. It led to her taking the stage at renowned clubs, earning Artist Of The Year at the 2023 Austin Music Awards, as well as features in Rolling Stone, Spin.com, Variety and the Cover of Austin Chronicle and many other publications. The buzz surrounding Wilson’s project has helped earn Sir Woman upwards of 30 million streams on Spotify.

Now, Wilson is funneling her long passion for soul, funk and R&B into a double album — If It All Works Out and If It Doesn’t. But making one — let alone two albums —isn’t something she ever intended to do. Throughout the making of both her records, Wilson experienced a great deal of loss. While recording If It All Works Out, her sister died. In between the making of her debut and the second LP, her father passed away. They were both chapters in her life that needed to be shared separately. “It basically came out to be an album for a good day and an album for a bad one, because you need music for both experiences.”

Throughout the 12 tracks of If It All Works Out, Wilson clung to the ideas of love, positivity and romance. The album’s cinematic lead single, “Who You Gonna Love” pays homage to a brassy Motown classic, while embracing Sir Woman’s overall ethos of lifting yourself up. “It was all the records from the 70s that I loved listening to growing up, I got to emulate and do my version.” “Heaven” is Wilson’s long-awaited understanding of the sentiment behind Bonnie Raitt’s iconic ballad “I Can’t Make You Love Me.” “It’s this shameless plea for one more night with the person that you love, even though you know, they don't want to be there anymore.” The album’s closer, “Making My Way” is a heartbreaking conclusion to the record that grapples with the gravity of loss Wilson experienced in such a short period of time. She began writing the first verse after her sister passed away (“I’m gonna see you again someday”) during lockdown when she was unable to have a funeral for her. For a while, she couldn’t move past that line. When it came time to wrap up the record, her father passed away. Immediately, the second verse came to her. “It was like the universe was making me wait to finish the song because it was gonna be connected to another major loss. So it was the most cathartic recording experience I've ever had. A song has never meant more to me.” 

While If It All Works Out has a hopeful lens, If It Doesn’t is the kind of album that can uplift you when you’re facing life’s challenges. The 10 tracks may seem uplifting on the surface, but they were crafted during one of the darkest times in Wilson’s life. As the lead single, the ‘90s R&B-tinged “Never Gonna Give Me Up,” is a cheeky, dance number that pays tribute to her music discovery in her teen years. “You never want to give me up / But you never want to give me love,” she sings with a playful lilt. On “Believe It or Not,” Wilson meditates on being enamored with someone who doesn’t believe them. “It is unrequited love, but you love this person so much that you don't care.” With “A New Story,” Wilson explores the power of reinvention. “I got in a conversation with someone who believes that nobody ever really changes, and as someone who just went through such a drastic change and came out the other side, a completely different human being. I was like, ‘This is absolutely untrue.’”

Ahead of the release of If It All Works Out and If It Doesn’t, Wilson will share a pair of singles from each record. Sir Woman’s If It All Works Out is due this fall, while If It Doesn’t is expected to be released in early 2025.