Where do I even begin when talking about Libby Callaway? She is a dear friend of mine, someone I’ve had the pleasure of getting to know over the last five years. Fashion Editor. Journalist. Creative Consultant. Libby has contributed to some of the country’s most widely regarded magazines and newspapers, from the New York Post to Elle, Style.com, Glamour, T Magazine and more. She’s worked as the marketing director for Billy Reid and media director for imogene + willie.
A former stylist and vintage clothing dealer, Libby is a noted secondhand shopping expert. Her unique personal style and advice have appeared on various outlets from Vogue to The Selby to The Today Show. And don’t even get me started on her closet!
Libby hired me as an intern back in 2012, and I can honestly say that it changed my life. A self-declared maximalist, our style is quite different from the other, though she is someone that I have the pleasure of calling both an icon and a mentor. I had so much fun playing dress up in her closet, and being shot in her amazing abode. A minimalist in a maximalist world. We shot Libby in my more minimal home, wearing new Goodwin pieces with her signature ‘Libby’ take on things. I hope you enjoy this conversation as much as I did.
The photos are shot by the inimitable Heidi Ross – it was truly an honor! Head over to The Callaway to hear more about the evolution of Pennyweight, Goodwin and my and Libby's friendship. And be sure to sign up for The Callaway Report, a bi-weekly newsletter featuring Libby's personal take on cool, creative Nashville people, places, things and happenings.
ELISE: When I think about you, I’m just so fascinated by all these different stories that you have… and I love that I can feel these stories reflected in your home and in your life.
Looking back to your childhood, I was curious how you imagined your life when you were young - what you saw for yourself.
LIBBY: You know it’s so funny, I’ve been thinking about this a lot lately - just about making plans, and how somebody told me I needed a five, a ten, a twenty year plan… and I’ve never had a plan.
I don’t know what that’s indicative of, or what that really means other than I guess I’ve always had confidence that things will work out the way they’re supposed to. That’s how I’ve lived a lot of my life, letting things happen and then taking the next step.
When I was younger I had things that I thought I wanted to do… I wanted to be Broadway actress and I wanted to be a politician.
ELISE: Two ends of the spectrum.
LIBBY: Exactly, and you know with all of these different things, I never thought about taking steps to get there. I took Poli-Sci classes when I got to college and decided I didn’t really want to do that. But I was always a writer, so that natural progression just happened. I’ve never really had a plan… and still don’t.
ELISE: That reminds me of something I think about often… this idea of rituals. I have this amazing book called Daily Rituals: How Artists Work. In your day-to-day life, do you have any kind of rituals or routines - some type of plan in that sense?
LIBBY: Yeah, yeah I do… When I quit drinking eleven years ago, I substituted exercise for feeling yucky in the morning.
ELISE: So is that how you start your day?
LIBBY: Yeah, I love how it makes me feel. I get up really early - like 5:30 AM, that’s when the alarm goes off at least. I make coffee and have my green smoothie and check emails… I know people say you should get up and meditate and not check your email first thing, but I can’t help it.
ELISE: I do the same thing. It somehow makes me feel more balanced to check in and at least know what I’m getting myself into before going about my day.
LIBBY: Totally. I think one of my things is that I have to have time alone. I’m definitely an introvert and I recharge alone. I do not like big crowds and I don’t like loud - unless I’m driving in my car and listening to music.
ELISE: That’s interesting. I imagine with your career, you have to be in a lot of large crowd and party situations. You are so good with people and connecting and seem so natural in that habitat. Do you feel like you’ve had to learn to be extroverted in those settings?
LIBBY: I’ve had to learn how to compensate, for sure. I say that I’m the most extroverted introvert you’ll meet, you know? I wear a lot of hats and work with so many people, which can be mentally exhausting. I have to get good sleep every night - my body just needs it.
ELISE: Absolutely. I think about that in terms of working and building this new business with Goodwin. I want to work hard and really do this thing, but I also want to build it to a place where I can step back a bit. Working less, but doing more, you know? Delegating or outsourcing to be more efficient, and freeing myself up to ultimately do more.
LIBBY: I’m still figuring out what that looks like and how to do it, because there’s also a public perception thing. Especially with social media! I’m naturally a people pleaser and hard worker, so I will do all the “shit” work - for lack of a better term, but I’m kind of done with that. I’m ready to own growing up in the company.
ELISE: That leads me to something I’ve always wanted to ask you: what is a lesson you’ve learned from a boss and what is a lesson you’ve learned from being a boss?
LIBBY: I’ve learned more from my bad bosses than my good bosses. My good bosses have been great and inspirational and encouraging, but I’ve had some really bad bosses. Most of them have been female and I think that’s really unfortunate… I believe that we should try to support each other as women in business.
But from them I learned about fairness and also a lot about vanity, and how vanity can take such a front seat. I don’t know… it’s been interesting to watch - especially in the media business, and especially now with social media where your image is such a big part of it.
At the same time, I think doing a great job at work sometimes is transcending that… I guess I’ve learned how that balance doesn’t work and how to actually make it work. I hope that as a boss I’m able to impart kindness and fairness and fun.
I like to think that I’m fun and unpretentious. I prefer to have a very friendly relationship with the people who work for me, but I want it to be honest too.
ELISE: Well I think I’ve experienced all of those positive things having had you as a boss. I feel like you’re really good at that.
LIBBY: That’s what I was going to ask you… what do you think?
ELISE: It is definitely always a lot of fun with you. I mean, you’re “Libby Callaway” and you have all this experience and connections and these beautiful, amazing stories. You’re so talented and clearly gifted in so many arenas, yet you are so approachable and easy to be around. You’re never pretentious and I’ve always loved that about you. You make everyone feel comfortable almost instantly, even though it can be easy to feel intimated around such a powerhouse with the industry experience that you have.
LIBBY: Good. Well, that’s what I was fishing for, so thank you. Haha!
ELISE: So on the topic of work, I’m curious about you not really having a plan. Do you feel you prefer freedom in work versus structure? Or do you need some kind of structure too?
LIBBY: It’s funny because I find that I end up being the one who asks for structure to be imposed… and usually that’s with clients. I need some parameters, but personally I don’t like my time to be micromanaged. So I guess I’ve gotten good at putting structure on my own work.
ELISE: Do you feel like being from east Tennessee has informed your work, or how you work?
LIBBY: I think it’s informed how I’m perceived.
ELISE: In a positive or negative way?
LIBBY: In a positive way… People used to kid me in New York and say when I needed something I’d get on the phone and bring out my southern accent. But I do think there’s gentility, kindness and hospitality that people associate with southerners and I benefited from having that association. Being nice got me everywhere, and it’s gotten me some pretty extraordinary places.
It was over the top – it was before 9/11. I took the Concorde to Nice one time with a bunch of supermodels to go to Cannes Film Festival.
ELISE: I’ve heard that story and it’s a good one.
LIBBY: It’s such a good one… and just so much stuff like that - things that don’t happen anymore. I saw the end of an era in media. I miss seeing those old news guys – being in a newsroom in New York with deadlines, people running around pulling their hair out, screaming across the newsroom at each other, ripping phones out of walls and throwing them at people. It was amazing and dramatic.
ELISE: Did you know growing up that you had a more unique point of view than most people?
ELISE: What about now? Do you feel that way at all now?
LIBBY: Yeah, I do… but I don’t think I became particularly self aware until maybe a couple of years ago.
ELISE: Me too. Maybe our paths overlapped on that.
LIBBY: Precisely. I went to treatment for alcohol and depression, and remember meeting with a psychiatrist on a regular basis. One day, I began reading his notes upside down because I kept wondering “what is he writing?” and it said something to the extent of “patient has lack of awareness.”
LIBBY: And he came back into the room and I was like, “Hey I just wanted to tell you that I was reading your notes upside down and I can’t believe that you would write that. I’ve been in therapy for fifteen years and blah blah blah…” but then a couple of years ago I was like, “he was so right.” I don’t think you ever stop learning about yourself, but I think it’s taken me a long time to get there.
ELISE: If you ever stop learning about yourself, that’s a scary place to be!
LIBBY: Oh yeah, very scary. I think I’ve come to terms with a lot of things. When I was younger I think I knew I was different in that I had a lot interests other kids my age didn’t, like I loved going to flea markets with my mom, or my second mom Gaye, who was this eccentric horse woman. Have I ever told you about Gaye?
ELISE: I don’t think so!
LIBBY: Gaye Romaine. She was married to a surgeon so she had money, and she had a daughter named Sally who was a little bit younger than me. Gaye was a ballerina and grew up dancing, so we always went to the ballet and the opera. She taught me to believe in fairies. We’d go see the real Santa Claus at the Phipps Plaza in Atlanta every year. She lived in this dream world.
Gaye taught me to have interests that were so different from home - it was like getting outside of a typical childhood. Though when I got older I realized she was totally deluded and quite crazy… she was a drug addict.
ELISE: I love that you had her to help stimulate your imagination as a child!
LIBBY: Yeah, she taught me to fall in love with New York. She knew everything about show tunes and would fly to Paris to take cooking classes… things like that.
ELISE: Your home and wardrobe are very bright and colorful. I always love seeing what you will wear. What drives you to create this type of environment, your home in particular?
LIBBY: It’s where I feel most comfortable. I remember when I went to college and decorated my dorm room, my roommate was like, “ohhh you’re bringing everything.” And then when I moved to New York, I filled up a whole minivan with stuff and most people were coming with two suitcases. I don’t do it half ass. I’ve got to be surrounded by stuff I love. I love my house and mixing it up, but I also love the familiar of where certain things are. And I think other people feel comfortable here, even though there’s a lot going on. Except maybe my brother-in-law, haha.
ELISE: When decorating, do you lean more towards form or function?
LIBBY: Oh yeah, form.
ELISE: Do you think about function?
LIBBY: Haha yes, I guess I do. The aesthetics of things are really what drive me. There are lots of things I have that are not used for what they’re intended for, because I like the way they look doing something else. I went through this phase where I bought a fake Louis Vuitton bag… it was good fake, but I used it as flower pot for a long time.
ELISE: I love that about you.
LIBBY: I appreciate all kinds of aesthetics. It’s not just my way or the highway. I feel like I really appreciate a good minimalist, and I appreciate a real conservative sister parish-type room in terms of design. I really love interior design. But the people who let their freak flag fly, that’s my favorite place.
ELISE: You have this way about you… of being so chicly over-the-top. It’s never too much, and it’s done in such an effortless way.
LIBBY: I think I’ve come into my own in that too… It’s so gratifying to get older. It gets so much better, Elise.
ELISE: If you couldn’t be doing what you’re doing now, what would you do?
LIBBY: Interior design. Right?
ELISE: That was easy. It makes sense because it’s such a natural progression from fashion.
LIBBY: Yeah, and it’s my mom’s family business. My mother is still doing it. They’ve been in their house for almost forty years and things are changing constantly – wallpaper or the kitchen or a new door going in.
ELISE: I’m so fascinated by your back story and what’s informed you to be an artist. I know all of these bits and pieces, but to kind of hear how everything comes together…
LIBBY: I think it’s still coming together… and once again, it’s like that whole self-awareness thing. Eleven years ago I thought I was fully baked. I thought cause I’d been in therapy, I knew all about myself… but then you get a little bit removed and you’re like, “I had no idea what I was talking about.“
I feel like I’ve lived a million different lives, and it’s really hard for me to be around people who constantly want me to be the person I was thirty years ago. I like growing and doing the unexpected.
ELISE: I love hearing that. I always want to be growing, learning and evolving.
LIBBY: I feel a comfort that I haven’t had before in my life right now. I think it’s realizing that I don’t know everything there is to know about myself and I’m going to continue to figure that out. I feel really embraced by Nashville, like my style and the way I live has been really accepted, which is nice.
ELISE: Do you feel like that has to do with the boom in Nashville that we’ve seen lately? More people here opening things up for a little more variety?
LIBBY: Yeah, when I was working as a stylist, it didn’t feel like there was an appreciation for what I could bring to the table. Now, people are more open-minded. Being a stylist was a very thankless job, but I learned a lot about Nashville while doing it. It has helped me see how much the city has changed over the last couple of years, and become more interesting and diverse.
ELISE: Do you think the overall the growth has been a positive thing for Nashville?
LIBBY: I do… of course it’s given me more opportunity to use different facets of my experience, like working at imogene + willie. That made me realize that I had something more to give than what I had been giving. They gave me a platform. I’ll always be really grateful for that.
ELISE: I feel like you did that for me.
LIBBY: You were the best thing to come out of that.
This interview has been edited and condensed.