Some conversations you wish you were recording. Jason and I have had about a 20 of those. And I haven’t even known him that long.

I met Jason through the vintage space, he’s a stylist, a curator, and honestly one of the most knowledgeable people I’ve encountered in this industry in a long time. He’s been in fashion for over 30 years. He travels, he hunts, he finds beautiful things and gives them a home. I’ve bought handbags and jewelry from him, pre-loved pieces that have single-handedly increased the value of my wardrobe at a fraction of what they’d cost new. An MCM here, a YSL there, a Cartier piece I still can’t believe I own. He curates with love and with an eye, and that’s rare.

When we’re in his space, whatever tent or popup he’s set up in, we end up in these deep, wandering conversations about fashion, about the industry, about the women we see and serve. We’ve always joked that we should be recording. So finally, we did.

On a call that seemed like it should’ve happened long ago, and could’ve gone on forever, Jason called me “a multi-hyphenate executive reshaping the fashion industry.” I’m still sitting with that one. Take a peek into our chat and scroll to the end to listen via audio instead.

— Keturah

A note on the transcript: brackets [ ] indicate thoughts I had but didn’t say out loud…the things running underneath the conversation. Enjoy.

Jason: Ms. Keturah, we are long overdue on a conversation. I’m so thrilled to have you here to talk about all things fashion.

Keturah: I am so happy because this has been a long time coming. We talk like this all the time. It doesn’t matter where I see you, I could see you in the line at a club (or the grocery store), I could see you at the train station. Wherever I see you, I want to talk to you.

Jason: And a little backstory between us…we haven’t known each other very long, but it feels like we have known each other for an incredible amount of time. I’ve been so taken by you. We’re connected through the vintage space, and your knowledge about all things fashion was evident from day one. To me, you represent the modern quintessential fashion executive, and honestly, I don’t have a face for that anymore. I know influencers. I know celebrities. But the fashion executive, that identity feels like a thing of the past. I see you as that.

Keturah: Thank you. It’s funny, when you said it, I tried to rattle off in my brain who I see as that. And all I can think of are the editors in chief. Outside of that, the people who actually work with the editors or at the brands, I don’t really feel like I have a grasp of that anymore. But that was always the goal. Growing up, when I thought about who I wanted to be, I didn’t even know this existed for me. I wanted to be some type of creative executive. It wasn’t even specifically fashion, because I didn’t know what a masthead was or what those roles looked like. So this is new.

Jason: I come from the era when I knew fashion executives at Saks Fifth Avenue, art buyers at W magazine, people of color in those roles, in those mastheads. So many of those roles have been obsoleted in recent years. There’s no longer that identity. But I consider the fashion executive the brass tacks, the engine behind the scenes. People don’t talk about them anymore. And I believe you are a bonafide executive. That’s what I want to drill down on today.

Keturah: Thank you. Some people think I’m an influencer because you have to have a digital presence now. But a lot of the work that happens behind the scenes, I don’t think people see that. Or the work that happened before I even got into this role. It took this role and that role and this role for me to even perform the way I perform now.

Jason: Let me give the audience a bit of background. Keturah Drake is a New York-based fashion executive, writer, and Director of Client Education and Brand Engagement at Tibi. Her career has taken an unconventional path through nearly every corner of the industry, beginning in advertising sales before moving into retail management. She later returned to school to earn her MFA in fashion, ultimately building a career in design, product development, and client-facing education. That uncommon journey has given her a rare perspective on fashion, not just how clothes are made, but how they are sold, worn, interpreted, and integrated into everyday life. At Tibi, she sits at the intersection of design and consumer understanding, translating creative vision of it’s founder into practical knowledge for women navigating modern wardrobes and careers. A wife, mother, educator, and lifelong student of fashion, Drake brings both professional expertise and personal honesty to her work. She offers what she describes as quiet but steady takes on what matters. No pretending. Just perspective.

Keturah: (laughing) You have to [introduce] and read everything for me going forward!

Jason: Your career path wasn’t linear. You started in advertising sales, moved into retail management, returned to school, and ultimately arrived where you are now. Looking back, what was the through line through all of those roles?

Keturah: The through line has been the ability to creatively articulate what someone else is trying to say, and also what I’m trying to say, with the lens of empathy. I’ve always wanted to help other people. There’s a helper in me. But helping wasn’t enough. Helping by doing what? By being in service, or by guiding and sharing things I’ve learned? I was raised partly by my grandmother, and she was a helper and a half. But I was also creative, and I didn’t know how to meld those things. That’s what I carry with me everywhere I go.

The through line has been the ability to creatively articulate what someone else is trying to say, and also what I’m trying to say, with the lens of empathy.

Jason: Was fashion the goal, or was it an accidental discovery?

Keturah: It wasn’t accidental, but I didn’t know the path to get there. When I was in undergrad at Tuskegee, I was making garments out of garbage bags, scented garbage bags. The colorful likely toxic pastel ones. I made a whole gown for the modeling troupe I was in. But I didn’t know how that translated into getting a job. My family expected me to be a police officer, a fireman, a teacher, a government worker. Those were the only options on the table. So I went to school for marketing to figure out how to make commercials. I didn’t know what a creative career looked like.

Then later after working at Walgreens as a store manager, I was working at Nordstrom and someone said, you should go back and get a master’s. I asked why. They said, in fashion, they have it at this school. I applied twice. I didn’t get in the first time. So it’s been like these little bumps along the way. I didn’t fall into it, but it wasn’t entirely intentional either. I just knew I wanted it, and people guided me toward it.

Jason: One of my observations about you is your exquisite personal style. Has that always been the case, or is this a later development?

Keturah: My friends say I dressed well in college, but I didn’t have much. I had a lot of hand-me-downs, my sisters were way older. Imagine somebody at 40 giving a 14-year-old something to wear. A shoulder pads and pleated wool skirt HATED to see me coming. I looked like everybody’s auntie.

But the women in my life were such keen dressers. My dad was a tailor. He and his first wife owned a cleaners together. [He was a street dude, but could sew a button, and press the hell out of a trouser.] Everything about how I looked, even if it wasn’t the highest quality, had to be pristine. [My mother and my maternal great-aunt are the same. You have to be ironed. Your undies couldn’t be in a bunch. Every small detail counted. Kind of how Andre Leon Talley was raised.] And I would get creative with how I styled myself.

I had one of those little pocket calendars, the plastic ones your grandmother keeps, that say something like “Jesus Loves You.” In high school, I wrote in those little squares what I wore so I wouldn’t repeat it. Because I cared about that.

Jason: If that focus was there at such an early age, this was clearly a foundational interest.

Keturah: Yeah. I used to draw Nike sneakers and redesign them with my friend, Lynn in the backyard. Which is funny because that’s what designers do now. We were always trying to recreate something. So yes. It was always there.

Jason: With all of these career experiences, what has this complete understanding of the industry taught you about how it really operates?

Keturah: At the end of the day, if you can’t market your product, you’re nothing. It’s really about how you speak to the product and how you speak to the consumer. If you don’t know the customer, there’s nothing you can do to serve her. You have to understand who she is, her demographics, her life, what she actually needs, or you’re not going to be able to reach her.

Jason: Speaking specifically to your role at Tibi, you’re really on the front lines with clients. How do you translate a designer’s intent into practical guidance that helps women build wardrobes that work for their real lives?

Keturah: What’s different for me is holding hands with so many different parts of a creative company. As a designer, my counterpart was a merchandiser, we had to balance creativity with what could actually be made and sold. Now I have to take into play every single part of the company. The wholesalers. What are the stores buying? What does a woman in San Francisco who works in tech need? How is she dressing?

So what happens is: I hear what the designer is saying and how she’s designing the collection. I meet with clients often. And when I meet with them, I can teach them how to wear the clothing because I understand what they need for different lifestyles. An executive needs something different than a woman working from home, or a woman who’s retired but used to be in corporate and is tired of blazers. There are so many nuances. Women, like Black people are not a monolith. It’s about breaking that down and really catering to that person, but in a compassionate way. I hear you. Now let me apply what I heard to the product and your actual needs.

Jason: I’ve experienced your influence firsthand. When you come to my vintage events and post something, I see how responsive your audience is. There’s a great deal of trust there. How do you think about that?

Keturah: It’s funny because I don’t even post that on my work page, I post it on my personal. And I still get the same engagement. There is a high level of trust because people know I’m not just going to sell them anything. Some people will say, you want a water? You want a car? Here it is. I’m going to talk about things that I know apply to the people I surround myself with. And to women in general.

For Tibi specifically, I’ve learned that our most underserved demographic is actually one of our most revered. Think about the woman in your age range (40-60s) who has lived a long and full life. She went from her college self to her young dating self in the city, to her married self, to her with-children self. And she’s been the same woman all the way through. But no one sees her in totality. They only see her for what she is right now.

I’ve had women say, you don’t know what I like. Because they assume I’ll put them in something predictable. So one of the questions I ask is: who were you in college? Who were you at 20? Because that gives me a taste of who you still are inside, that maybe you forgot, or lost…[We are all in the process of remembering and finding ourselves].

“Who were you at 20? Because that gives me a taste of who you still are inside…that maybe you forgot, or lost.”

Jason: You’ve written about losing your love of fashion during your years in corporate design. The classic cobbler with no shoes problem. What happened, and how did you find your way back?

Keturah: The word joy almost made me tear up, because I can remember when there wasn’t joy.

When I imagined design, I thought it would be this beautiful, fluffy position. I’d be illustrating in a showroom somewhere. And it was not that. In an era where you needed schooling to open the door, not a [perfectly curated] Instagram account, I was making tech packs… It was [so] unglamorous. It was production-oriented. It became about looking at collections to see what you could knock off, because you had to make a version of it to see at mass. And that rips your soul out when you know how things are made and you wanted to make something real.

After freelancing and feeling like this doesn’t feel good anymore, I started designing things on my own. Didn’t realize how expensive it is. I bought some fabric, $5 a yard. They said, ma’am, you have a minimum of a hundred yards, and after duties it’s going to be $23.99 a yard. And I was like, oh. Maybe this dress does have to be priced higher.

But what shifted was Covid. A shift in my age. Coming into myself. And motherhood…I had a child and I felt like, wait. I’m back. I’m a woman. Changes in life do that to you. Grief. A job transition. I felt so empowered and I started showing up as my most authentic self.

And part of it was accepting my body. I’ve always been a tall, curvy girl. Waiting to have the “perfect” size to dress was not an option. I’m going to show up and I want to express myself, and I want you to see me the way I want you to see me right now. It doesn’t have to wait for later.

“Waiting to have the perfect size to dress was not an option. I want you to see me the way I want you to see me right now. It doesn’t have to wait for later.”

Jason: Would you consider your journey tumultuous? Did you have agency throughout?

Keturah: No agency whatsoever. And I’m sure someone would say, you had some agency. But I don’t think I did, because I didn’t know my worth. If I had known my worth, I would have taken the agency. I thought I was beholden to someone. I thought I had to do this for them to see me as that…[that agency was about reciprocity]. I wish I had figured that out a little earlier in my career.

“I didn’t have agency because I didn’t know my worth.”

Jason: What role do you think clothing plays in identity today? Is it still primarily self-expression, or has it become something more complex?

Keturah: It is so complex, but also so simple.

I study people now. I look at someone and think: what did they want to convey today? And sometimes I don’t think it’s what they wanted to convey, it’s what they wanted to feel. If I see you in sweats and a tee and you left the house and weren’t going to the gym, you probably wanted comfort and convenience. But you didn’t land on what you wanted to exude. And so the chaos ensues, because people in the world treat you how you look. Perception is reality. And then you don’t feel good about that. And it becomes a cycle.

I study people now. I look at someone and think: what did they want to convey today? And sometimes I don’t think it’s what they wanted to convey, it’s what they wanted to feel. But you didn’t land on what you wanted to exude. And so the chaos ensues, because people in the world treat you how you look. Perception is reality. [I’ve seen and found this out for myself a myriad of times].

Using clothing to speak for you, to speak with you…is soooo empowering. And it’s been something people look down on. Like, if you’re into clothes you’re vain, or you spend a lot of money. But if you’re into style, into how you show up, that conversation gets lost.

Our parents, our ancestors…there were nuances to how they got dressed and what they cared about. They didn’t just show up any kind of way. And whatever your flavor is, you can show up in the most powerful version of that.

Jason: Was reading people a gift, or something you developed?

Keturah: It now feels like I’ve gotten my 10,000 hours in. If I count everybody’s shoe size for three train stops every Tuesday for 17 months, I’m going to know who wears a 7 and who wears a 10. [This is what I do. I train myself to see people.]

But paying attention to people, that started early. In church, I would watch how the women sat. When they crossed their legs. I wanted to wear a church hat and a matching suit. That was my whole goal. I was always wanting things that were outside of myself. Observing things. And now it’s observation and practice combined. It’s just in here.

Jason: Your Substack, Low Key Important, began as a place to discuss style but has evolved to include grief, motherhood, ambition, personal growth. What made you decide those subjects belong alongside fashion?

Keturah: Because of the data points I collect when I speak with clients. The amount of people who send me a picture and say, I have to go to my father’s funeral, what do I wear? Every person getting dressed for whatever they’re going through still has to show up. Grief. A job transition. Postpartum. The postpartum woman is in deep change but also in the constraints of home and comfort. She wants to feel like more than just a mother. I’ve experienced that.

I lost a friend (Lendrell Martin) last year. He had a beautiful Substack. We used to talk about fashion and how important it is to see beauty, to be beauty, in whatever form that takes. And I don’t know, it’s all connected.

Jason: How has motherhood changed your relationship with style and confidence?

Keturah: I went to a show (the Pyer Moss show at Madame CJ Walkers estate) a month after having my daughter. I had breastfeeding pumps on under my dress. I was determined. And I remember feeling so good to just be out and be seen as myself, not just as a new mother.

Who you were before is still who you are after, just an enriched version. And you’re also caring for someone else. Being able to pivot back to a self-love of just getting dressed is the goal.

I used to put lip balm in my daughter’s diaper bag because I kept forgetting to put it on. My lips were cracked. I wasn’t drinking water. I had to put it near the baby just to remember myself. If that’s what I had to do to remember lip gloss or balm, imagine how hard it was to get fully dressed.

But when I take care of myself and show up for myself, I can also help someone who doesn’t know how to do that yet.

My daughter is 5 now and very into fashion. She has opinions. Usually they’re right. When she says, not that shoe, I listen.

Jason: You said that not sharing more of yourself eventually felt like a disservice to your readers. What changed your thinking about the line between personal and professional?

Keturah: Working as one of the faces of a brand, I felt like I had to limit myself. But I can’t feel like I’m authentically being myself if I’m not sharing these things. And when we share, that’s spiritual to me.

The more we share, the more connected we feel. And that connection is never just about clothes. It’s about the humanness of all of us. No matter where we are, who we are, what we’ve been through.

I’m in a season of sharing. I haven’t always been. My personal Instagram was dry. But in this era, especially with AI and so much that’s being crafted and inauthentic, you have to release a little. This is really who I am. This is what makes me different. There’s always somebody out there who is your person. Even if it’s another executive who just wants a friend. My grandmother always said, “there’s a lid for every pot”, and that’s true.

Jason: Have you encountered your own version of the glass ceiling?

Keturah: Yes, more so in design. In design it’s almost like academia. You have an assistant, an associate, a director. And if those roles are filled, there’s no room for advancement until someone leaves. I’ve worked in smaller [garmento-like] companies places where if I’m answering to the owner, there’s nowhere to go.

This is the first time in my career where my expertise, my skills, and my experience have combined to make something untraditional happen. And I think we have more power than we realize. If someone came to me now and said they don’t have a pipeline, I would tell them: get on social media and create one. That tool is right there.

Jason: Where do you find the greatest joy in the work today? Is it in the clothes themselves, or in the transformation they unlock?

Keturah: It’s not in the clothes at all. Clothes are just the vehicle.

It’s 100% the transformation. Not even the big transformation, the touch points. Every conversation feels powerful. When someone feels seen and heard. When they feel like they can show up better, and maybe they didn’t have the tools before to express who they are visually. That is the unlock. That’s why makeover shows work so well. We’re locked in. Because people like to feel better. When you tell someone to try something they wouldn’t have tried themselves, and they put it on, and you can feel the energy shift, you know you’ve done good. You got her something that’s going to make her show up in that office in a whole new way.

“It’s not in the clothes at all. Clothes are just the vehicle. It’s 100% the transformation.”

Jason: Thank you so much for joining us.

Keturah: I loved chatting with you. Every conversation we have, I always wish we recorded it. And now we have. I don’t know how to mind my own business. Maybe you don’t either. And that’s not a problem. It’s a good thing.

The Real Situation with Jason Campbell is now live on Spotify, YouTube, and wherever you stream podcasts.

Find Jason on Instagram and on Saturdays at the Chelsea Flea Market.

Find me at @keturah.tibi and @k2ra. Available for virtual styling here. To chat email me at stylerevivalnyc@gmail.com

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