Woman of the Month: Kailey Dickerson

In our latest series, we’re bringing you stories from women who are chasing their dreams and building a life that they love with New York Country Swag’s, “Woman of the Month.”

Each month, we will highlight a different female pursuing her passions. Introducing you to women who are taking risks, working relentlessly and turning their dreams into reality. These are empowering women who serve as role models and should be celebrated.

Our February NYCS Woman of the Month is: Kailey Dickerson

Kailey Dickerson

Photo: Facebook via Kailey Dickerson

Kailey Dickerson, wife of country singer-songwriter, Russell Dickerson, took time out of her busy schedule to chat with New York Country Swag about her journey. Growing up in Wisconsin, the only girl in a family of five older brothers, Dickerson learned the importance of family very early.  She became an aunt when she was only eight years old and proudly explains that she now has twelve nieces and nephews, a constantly growing family. All through school, Dickerson played soccer and tennis and grew up dancing and performing in musicals, which led her to Nashville’s Belmont University where she eventually met her future husband, Russell.

Kailey Dickerson

Photo: Facebook via Kailey Dickerson

While at Belmont, Dickerson realized pretty quickly that she did not want to pursue a career in performing, but rather found a love for photography. She shot album covers and music videos, and began to follow this new direction. “I didn’t like being the performer, but I liked helping people feel better about themselves by taking pictures and hearing people be like ‘I didn’t know I could look like that in a picture,'” she tells us.   Teaching herself photoshop and how to edit videos, she credits the “fake it til you make it” method worked best for her.

“Careerwise I’ve never been the girl that’s like, ‘this is exactly what I’m going to do and this is how I’m going to do it.’  It’s always kind of happened piece by piece,” she explains.  One of her dreams was to shoot mission photography, so for two to three years she traveled the world taking pictures for all different organizations.

Launching her own photography business, Kaileyography, Dickerson shot for blogs like The Vogue Trip by Hayley Hubbard, wife of Florida Georgia Line’s, Tyler Hubbard. As well as Womanista by Cassie Kelley, wife of Lady Antebellum’s, Charles Kelley. Later, Dickerson traveled to Uganda with Thomas Rhett and his wife, Lauren, to take pictures of the adoption process of their beautiful baby girl, Willa Gray.


Willa Gray

Photo: Kailey Dickerson for People Magazine

The importance of family and her faith has always been something Dickerson kept at the forefront of her life, knowing that God would provide for her and Russell no matter what the circumstance. “Once we got married you couldn’t really tell where he ended and where I began and it was so seamless and how it had to be to make it work, because we were independent for so long. We don’t come from tons of money where our families can help and we just had to do it ourselves and we did.”

After shopping around for record labels for Russell, the couple eventually decided to release his first single, “Yours”, independently.  They shot a music video for the song with Kailey behind the camera, while God put on quite a show for them. As the video rolls, Russell walks in the rain while incredible lightning strikes behind him, creating a spectacular effect in the now famous “$6 Video”.

Dickerson traveled with her husband as his career began to skyrocket to the top. Playing several roles, fans could find Kailey working the merch table, taking pictures and videos at his shows and even driving the bus from city to city. “We would all take turns. I liked my early morning shift when the sun starts coming up. I would get my Starbucks and just start driving,” she laughs.

Kailey Dickerson

Photo: Instagram via Kailey Dickerson

Over the past two and a half years, she stayed by Russell’s side while he played over one hundred touring dates, keeping them together and their marriage strong.  As “Yours” hit the radio charts ultimately topping the charts last week and spending now two weeks at number one, Dickerson is just grateful for the incredible blessings they have achieved together.

When she is not traveling the country with Russell, she loves being home on her couch watching Gilmore Girls. She also credits everything The Bachelor/The Bachelorette as her guilty pleasure along with coffee and wine. Recently she has started writing as a creative outlet. “It is kind of removed and has nothing to do with Russell, so it’s my own little corner space. I’m in the process of writing a book. I flip flop between a book and a blog,” she explains. “I haven’t landed on where that will be yet, it’s more of the dating relationships thing that I love so much, kind of like ‘Coffee with Kailey’ turned into paper.”

We are proud to name Kailey as our February Woman of the Month and look forward to bringing you more inspiring stories, celebrating women who are pursing their passions and empowering others.

Follow Kailey’s adventures on Instagram here. For more about Kailey’s other half, husband – Russell Dickerson, follow him on Instagram here and listen to his debut album, Yours, here.



Thanks for supporting Country Music in NYC!

Click Here to learn more about NYCountry Swag
+ Follow our Country Music Adventures on Instagram, @NYCOUNTRYSWAG!

– Team NYCountry Swag