This Cleveland, Tennessee native is recognizable for her gorgeous red locks, eye-catching style (largely defined by vintage pieces) and exuberant personality. She took her love of fashion to New York City, where she jumped at the opportunity to write for the New York Post, one of the many things that prepared Libby Callaway for the life she now lives. Today, she’s fully satisfied sharing the stories of standout brands and promoting them through her company, The Callaway. Libby’s love of work is rivaled with a love of vintage shopping and being social over food. We cannot toot Libby’s horn loudly enough. Her authenticity, commitment to the community, diverse talents and covetable closet are only a few of the reasons she is featured as today’s FACE of Nashville.

Libby Callaway: FACES of Nashville
Welcome Libby Callaway as today’s FACE of Nashville!

You have spent time working at the New York Post and freelancing for various publications. What is the most memorable story you have covered?

The most memorable stories to me, personally, were some of the more unique and unexpected pieces I did for the Post. That paper is famous for its quirky takes on features; they love playing against convention. During my time there, it was very much anything goes: far-out ideas played well with my editors.

That’s how I found myself on assignment on the Upper East Side, in a town car with André Leon Talley, who was then an editor at Vogue. I took him consignment store shopping for his first time. We went to Michael’s, where Jackie Kennedy used to consign. (I think I blew ALT’s mind with that piece of trivia.) Or skulking around outside L’Avenue in Paris with Michael Kors, scouting chic women to photograph for a story about how Americans interpret French style (fun fact: Michael was once the designer for Céline). I also loved the stories I wrote about only-in-New-York cultural phenomena, like sample sale catfights and dumpster diving outside the old Condé Nast offices on Madison Avenue. I also did some pretty unforgettable “experiential” stories, too, like taking lessons from a high-end dominatrix that worked out of an office building in Midtown, or spending the day on Rodeo Drive getting dolled up for Oscar week parties courtesy of Chanel and Frederic Fekkai. Never a dull moment at the Post.

What drew you back to Nashville?

I was tired of New York. Nothing was wrong. To be honest, my career was gangbusters. I had a plum position at the Post, and they gave me great play. I had a photo byline and sat on the front row at every fashion week — things that define success in NYC fashion media circles. Big magazines were trying to poach me. But the idea of a future in publishing just wasn’t appealing. Plus, I was tired of having to work so hard to just be. Everyday life is hard in New York. I wanted a life that was easier, not to mention a community that was softer and friendlier. And I wanted to be back in the South. So Nashville fit the bill.

On a very practical note, I knew that Nashville’s creative business infrastructure could support me if I ever wanted to leave journalism (I moved to Nashville to take a job at The Tennessean). I knew I could parlay my fashion connections into some kind of gig in the entertainment industry, which is what I did when I started working as a stylist.

Libby Callaway: FACES of Nashville
How does she start each morning? Early, and with a green smoothie and at least two cups of coffee.

What services does The Callaway offer?

I started The Callaway about a year and a half ago to cater to the creative community I saw growing up around me.

Our company tag line is “Content, Curation, Communication” — sorry, a love of alliteration is something I picked up at the Post and have never quite been able to let go! Content creation is centered around writing, for the most part: bios, press releases, website verbiage and other collateral. Additionally, I’ve had a major role in the creation of several fashion brands’ successful blogs, so I offer that as a more extensive creative service. Moving on, curation is a c-word for strategy, which usually takes shape as a comprehensive marketing plan. And communication is just another way to say public relations.

Although I will take on content creation work on the side, when you come to The Callaway as a brand looking for help with exposure, we don’t piecemeal our approach. We use the combined power of all three pillars to support our clients in a way that’s prescriptive, based on their individual needs. They’re very special snowflakes, these Callaway clients.

Tell us about a few of the local brands you are representing.

The Callaway’s current roster spans fashion, beauty, design and hospitality — I love that we are able to cater to such a broad range of clients. Keeps things lively, for sure!

On the fashion front, we have Cavanagh Baker and Ceri Hoover, two local designers who specialize in high-end womenswear and accessories, respectively. We also represent Kotn, a Toronto-based brand that makes incredible Egyptian cotton basics. Speaking of beautiful fabric: Andra Eggleston, who designs textiles under the name electra eggleston, is someone we’ve worked with for quite a while now.

Over in our beauty division, we have Poppy & Monroe, the clean beauty collective located in Germantown. They’ve been great fun to work with, especially on the heels of doing the PR to launch Clary Collection, which is a really excellent local line of organic body care made in town. In a neat segue, Clary is being sold at Etudes, the brilliant new retail concept in Edgehill Village from Ivy and Josh Elrod of Wilder. We’re helping the Elrods get the word out about Etudes’ recent opening (go see them now!).

Hospitality is a growing area for The Callaway. In April, we worked with Miranda Pontes to open Lulu, her new fast-casual restaurant on Jefferson Street. And coming soon: the announcement of a new hotel located downtown on the corner of Fourth and Church. I’m curating the retail store, which will feature exclusives from Nashville area designers and makers, and The Callaway is doing local PR. There are so many great local stories to be told related to this place. You’ll be reading about it a lot in the very near future.

The Callaway has several other very cool projects in the pipeline, including collaborations with a major international brand or two. I can’t wait to go public with them soon.

Is there one thing all of these brands have in common?

Excellent product and a unique point of view. And they are all owned by nice people who work hard.

When it comes to clients, The Callaway has a “no jerks” policy (me and my potty-mouth normally use a different word for jerks). I don’t care how great their clothes are or food tastes: I can’t work with someone I don’t respect. Kindness, graciousness and a good work ethic are non-negotiables. I only want to collaborate with people who care passionately about what they’re doing – that’s the only way I can get truly invested in what they’re doing.

Welcome Libby Callaway as today's FACE of Nashville!
“I love to work – truly. It’s fun. But I do try and turn it off from time to time,” Libby tells us.

Through The Callaway Report, you help us get to know tastemakers around town. What led you to start this newsletter?

The Callaway Report (TCR) started as a way to keep my Nashville-curious out-of-town friends in the know about all the amazing things happening here. I was going to send out a bi-weekly email to my media pals listing five marvelous things or events happening in town. I know a lot of incredible local photographers, so I decided I’d run the copy under a beautiful original photo. But when I started talking to my camera-wielding friends about contributing, I found out they were keen to shoot bigger projects. So I changed my focus a bit. TCR now publishes interviews that sometimes run over 3,000 words, accompanied by up to 20 photos. I am super-proud of the 20 posts we’ve done over the last year and a half!

What makes style in Nashville distinct from other fashion cities — we can call Nashville a fashion city now, right?

Nashville is absolutely, positively a fashion city! Our designer community is thriving, and the infrastructure around our industry – yes, industry – is growing every day. Earlier this year, our local trade organization, the Nashville Fashion Alliance (NFA), released the results of a major economic survey that found that the local fashion industry contributes $5.9 billion to Nashville’s economy and employs 16,000 people. Sixteen thousand fashion workers sounds like a city unto itself, no?

Thanks to the work of non-profit and volunteer groups like the NFA and Nashville Fashion Week, Music City is becoming known as Fashion City on the national and even international stage. I’ve served as board president of the NFA for the last two years, and during that time, it’s been incredible to watch our city and region grow in influence. NFA CEO Van Tucker, her team and the rest of the board have been tireless in the quest to carve out a space for Nashville in the national fashion consciousness. It’s paid off with major stories in the New York Times and Business of Fashion, not to mention a strong relationship with our friends at the Council of Fashion Designers of America (CFDA).

Welcome Libby Callaway as today's FACE of Nashville!
“I’ve been wearing vintage since I was a little girl. My mom used to dress me and my sisters in antique dresses when we were children. I started collecting vintage myself when I was in high school,” Libby shares.

How would you describe your approach to fashion and style?

I look at clothes as opportunities to have fun and be creative. Getting dressed in the morning really makes me happy – even if it’s sometimes a challenge. If I’m feeling off, I’ll often try on five different things before I leave the house in the morning and still come home after lunch and change again. I’m fickle, but being happy with what I’m wearing has an enormous bearing on my mood.

Style-wise, I’m a committed maximalist. My closet is filled with lots of color, patterns and prints — it’s kind of awesome, if I do say so myself. This summer, I’m trying hard to wear things that haven’t gotten the love they’ve deserved over the years. I feel like I have a new wardrobe!

Where can we find you hanging out around town?

I’d never leave East Nashville if I could help it. I try to support neighborhood restaurants and retailers as much as I can – the fact that we’re getting more of both is thrilling to me and my fellow 37206-ers.

I relax by vintage shopping at High Class Hillbilly or checking out the antiques that Deb and Wayne have unearthed for Wonders on Woodland. Andy Mumma is going to be able to retire on what I’ve spent on pour-overs at Barista Parlor … I’m a fool for Mas Tacos, though Marché never disappoints. For dinner, if I’m not at Margot, I’ll venture “across the river,” usually to Germantown. City House and Rolf & Daughters are always dependable, to say the very least.

The draw of eats across the river is enough to get me to cross a bridge. For the last two Friday afternoons, I’ve met friends at the bar at Henrietta Red for oysters during happy hour. I feel like this is a marvelous (and delicious) tradition in the making. I also frequent Little Octopus and Lulu, especially for lunch. And I love Bastion for dinner. It’s fun to order the whole menu to get to experience all that Josh Habiger has dreamed up that evening.

What is the best piece of advice you have received and from whom?

I have been sober for 12 years. During that time, I’ve been involved off and on in 12-step programs. In the “rooms,” you hear a lot of slogans and phrases designed to help those struggling with recovery describe and deal with challenges in life, both big and small. At different points, I’ve heard folks talk about “walking through the fire” – meaning, staying the course and bearing the heat of a challenging situation or phase in your life, knowing that it’s not forever. I think of this when times are tough. It’s a comfort living with the knowledge that if I can just handle the hot seat for a bit longer, there will be better times ahead.

As Chairman of the Board of the Nashville Fashion Alliance, the growth and ongoing health of Nashville’s fashion industry is very important to Libby.

What books can be found on your bedside table?

I can’t read fashion magazines in bed, so Vogue, W, et al are stacked up beside my reading chair in the kitchen, to be tackled on Sundays after the Times. Longer form reading is for nighttime. I have a huge stack of books and magazines on the floor beside my bed. There are always at least four issues of The New Yorker there, waiting to be read, along with The Atlantic and New York Magazine.

As far as books go, I started Joan Juliet Buck’s The Price of Illusion in April and am savoring it slowly. I have Joan Didion’s latest, South and West, on tap next. Finally, there is always a copy of Out of the Vinyl Deeps, a collection of essays about rock and roll by my late grad school mentor, the feminist writer Ellen Willis.

What are three things you can’t live without excluding faith, family and friends?

My computer, great food and lots of coffee.

Sign up for TCR here, and you can track the changes of The Callaway Report for yourself!

Thank you to Libby Callaway for giving us a glimpse into your life and to Ashley Hylbert for the stunning photos shot inside Libby’s East Nashville home. 


Beth Brown speaks from experience, which is why she is such a valuable member of TriStar Centennial Medical Center’s Intimate Partner Violence (IPV) Task Force. Meet the newest FACES of TriStar.

About the Author
Alex Hendrickson

Alex is a Southern writer known for hunting down delicious stories and traveling the world with hunger. Her passions and interests lie in food, travel, interior design and inspiring people, and her dream is to eat a dozen oysters a day.