Google “Libby Callaway,” and what you’ll see is a collage of bright colors and expressive prints on a slender, tall body topped with long, wavy, fiery red hair. These images perfectly represent the essence of Libby Callaway - a walking storybook and visual art museum. 

Often found zig-zagging through her favorite East Nashville spots - Libby is a woman on the move. And when she sits still, it’s either in her gorgeous custom-designed bathtub (“with someone else if I’m lucky!”), or in a colorful corner inside her purple home, named “The Callaway Compound,” making sequined ornaments. 

A fashion journalist-turned-PR guru in Nashville, TN, after Libby spent time working as the media director for Nashville denim company imogene + willie, and marketing director for the Alabama fashion house Billy Reid, she started her company The Callaway, which she categorizes as “making small businesses big and big businesses small” through intimate events and meaningful partnerships. 

Her interview responses are just as fun and colorful as she. Read along to dive into the whimsical musings of Libby Callaway.

Libby Callaway

Can you tell us a bit about how you ended up in Nashville, and what makes you want to stay?

When I was ready to leave New York in 2004, I knew that Nashville was where I wanted to be. I have a lot of friends here and would visit frequently. It’s laid back but not passive, which I appreciate. When I was making the choice to come here, Nashville’s entertainment business was a deciding factor: I knew that if I ever wanted to leave the world of daily newspapers, I could mine that industry for a gig, which is what happened when I moved on to work as a stylist. I’ve been here 20 years now, other than an 18-month stint when I moved back to NYC. I don’t have plans to leave — I love my life here. But never say never!

You’ve spent a good amount of time in bigger cities like New York - how would you say Nashville’s “vibe” compares? 

Folks always want to draw comparisons between Nashville and New York or LA, but I like to think of this city in its own right. The culture of Nashville is much less hurried or panicked than that of other big cities. At first, this made me insane: I like to move quickly! But honestly, it’s a blessing. It’s taught me to slow down, at least a little.

Can you share the story behind The Callaway and what inspired you to start your own PR business?

After I made the move from journalist to PR, I led the marketing departments for two fashion brands (imogene + willie and Billy Reid) before deciding to do my own thing. The timing of my move to Nashville was perfect: I had a few years under my belt by the time the media declared us an “It City” in the late aughts. That, combined with my New York media savvy (and the Rolodex I’d grown there), made my experience a boon for both smaller local brands looking to scale nationally and larger, out-of-town companies who were landing in Nashville for the first time and needed help finding their audience. I like to say The Callaway makes small businesses big, and big businesses small. Basically, I saw voids in the luxury fashion, hospitality, and design markets and knew I was the person to fill them.

Libby Callaway

Can you tell us about The Callaway Compound…? How do you find eclectic and cool objects to fill your space?

Like my closet, my home is predominantly filled with vintage, antique and secondhand pieces that I’ve acquired over my lifetime or that have been handed down from my family. My mom’s family’s business is interior design, so I grew up around a home that was always changing. I take a lot of inspiration from my mom, who has never been afraid to try new things in my parents’ home. I also love to hit antique stores and flea markets, and I don’t need them to be nice. Some of my best finds have come from incredibly crappy holes in the wall.

What challenges have you faced in the journey of building The Callaway, and what valuable lessons have you learned along the way?

The main lesson I’ve learned — and it has not always been easy — is to be adaptable. My business was thriving before Covid; at one point I had nine employees on my payroll. I let them all go two months into lockdown and have since been working on my own, as a consultant (I hire freelancers when I need help). It was heartbreaking and I mourned that decision until recently, when I was finally able to pick myself up and start to rebuild. I have a lot of work capital left to spend, and I try to think about it with enthusiasm instead of letting it scare me. 

Can you share any exciting collaborations or future plans for The Callaway that your community has to look forward to?

The most exciting projects on my roster are rooted in hospitality. I am consulting on a few new developments in Nashville, as well as a new boutique hotel that’s coming later this year.


One of our favorite mottos here at HART is “Memento Mori,”  – how do you find ways to celebrate everyday life and live it to the fullest?

It’s pretty simple: I try to be grateful for what I have, especially my family and friends who support me. I also try to tell them this often!

What’s on your nightstand?

A humidifier, Kleenex, my phone, and a red lacquered tray holding Clary Collection balm, THC salve, and a bunch of rubber bands that I’ve taken off in my sleep.

What is in your purse?

A small YSL wallet, a pouch with about six different lipsticks (Dou Dou by Gucci Westman is my go-to when I need a no-lipstick lipstick look), and about five Target receipts.

Worth the splurge? 

Latisse. I have it to thank for my Bambi lashes.

Favorite book? 

Always the books I’m reading at the moment. Currently, that’s Slow Noodles: A Cambodian Memoir of Love, Loss and Family Recipes by Chantha Nguon (my pal Kim Green contributed) and American Flannel by New York Times Styles Reporter Steven Kurutz.

Favorite podcast?

Smartless, which allows me to wallow in my Jason Bateman crush for an hour every Monday morning.

Go-to mocktail? 

NA wine is great. My current favorite is an extra-dry Sangiovese by Zeero

Most worn shoes? 

Lately, my new-ish black suede Lucchese boots. I am a recent convert to Western shoewear and don’t plan on looking back soon.

Must-have makeup product?

My Shiseido eyelash curler.