An Interview with Kelsey Keena

Kelsey Keena is a 23 year old vintage enthusiast, fashion blogger, and business owner. This week we talked to Kelsey about fashion, feminism, and her work hustle with her brand Over the Hill Vintage.


DE: Hi Kelsey! Tell us about yourself! 

Kelsey Keena: Oh goodness, it’s always a challenge for me to just say something about me. But, I’m a 23-year-old girl, with an old soul, from Fullerton. I like to tell people I’m a professional hoarder, and I have an obsession with Dr.Pepper.

DE: What made you decide to start your own company and where did you get the name Over the Hill Vintage?

KK: I’ve always had a passion for vintage, even when I was younger, honestly because I didn’t have enough money to afford name brand items. After leaving a job where I wasn’t happy, I knew it was time to combine my two passions of thrifting, and show people the power/beauty of being different. Over the Hill got it’s name honestly, because I thought it was funny to say that the clothing “ was so old…get it?” But I feel like most people have a negative perspective about getting older, however I think it’s beautiful to go triumph bumpy hills, and being new chapters in our lives. So I like to think that the name Over the Hill Vintage represents a new chapter.

DE: How did you juggle school and starting Over the Hill Vintage?

KK: Honestly, I don’t know. Over the Hill is such a passion of mine that I made it work, I love working on my brand so much that it’s not work. I know it sounds cliché, but I have so much fun doing what I do now. Being a homebody has certainly made it easier, since I don’t go out to parties or social events a lot. I know it’s hard to do since I am so young, but I feel like what I’m striving towards is bigger than Taco Tuesday. It’s hard for some to come to that acceptance, but I know that focusing on my brand and school is the priority right now, so I just made it work haha.

DE: Managing school, work, and life is a lot to put on your plate. Who’s your biggest support?

KK: Hands down, my main supports are my Mother and my boyfriend, Pablo. When I first introduce the idea to my Mom, she never once said not to do it. I remember her telling me that it wasn’t going to be easy, handed me little sale receipt booklets, and told me that I’ve never been afraid of a challenge. Pablo, helps me with the everyday decisions, and has stood by my side while I made/making my dream come true. He doesn’t understand a lot about vintage, but it’s always extremely helpful having an outside view. They have both been my support during the hard times, and successes. I wouldn’t have it any other way.

DE: What advice would you give other young women who want to start their own business?

KK: TO JUST DO IT! As someone, who has been wanting to do it for so long, I can’t believe I waited this long to start. I’ve learned that of course it’s a risk, but your overall happiness is worth starting on your passion. Life is too short, so start today. This all sounds extremely cliché for me, but honestly when it comes to down to it, I can’t stress enough about the importance to just saying yes to opportunities.

DE: What are some of your favorite pieces in your shop right now?

KK: My favorite items at the moment right now, are all from my lingerie series, I just came out with. I’ve never been a Victoria Secret girl, and I was never into the huge push up bras. However, I’m a sucker for a matching PJ set. I feel like the lingerie series is still very much sexy, yet modest all at the same time. I just love finding pieces that can make a woman feel empowered.

DE: You worked in retail before launching your business. How has working for yourself differed from working for someone else?

KK: I’m very much a people pleaser, so when I was working for a company/someone else I always knew what the expectation was, and how to meet or go beyond that. Working for myself, makes it even more difficult, because I’m extremely hard on myself. I have so much drive and motivation to have my brand be at it’s prime, that sometimes I have to tell myself that it’s okay if things are not perfect right now. Pablo told me once, that it’s okay that once all the seeds have been planted, to enjoy watching them grow at their own pace. It’s something that’s stuck with me, since I started being my own boss.

DE: What’s the most rewarding aspect of your job? What’s your biggest challenge?

KK: The most rewarding is the extremely supportive community. Walking into this business, I wasn’t sure what I was doing! I graduated with a degree in English for goodness sake! Having a core group of kick ass ladies, is what helps me stay humble yet always hungry for more success. The biggest challenge is to not get caught up in the politics/ drama that can happen in any business community. I just try to focus on how I can perfect my own brand instead of comparing myself to others.

DE: Retro silhouettes seem to celebrate curvier figures more than modern fashion does. Do you feel retro style fosters more body positivity?

KK: Ahhh, I would say yes and no. It’s never a straight answer with me! I would say yes, I having a curvy body myself; vintage clothing just melts onto my body in ways I would never imagine. However, with modern sizing in comparison with vintage sizing it can be quite difficult. I’m considered a purist when it comes to vintage clothing, I don’t like to touch or up cycle when it comes to vintage. I believe the clothing is perfect as is, so sometimes it can be a challenge finding things in my size, but it makes the hunt that much greater.

DE: How has your feminism impacted your career ambitions? Where do you want your brand to go?

KK: Feminism has been a core value within my family, since I was young. However, I like to think that everyone is a feminist, and wants equality for everyone. But, I just use my brand to now be a voice to represent feminism, and I try to speak out for those who might not feel the confidence to yet. I want my brand to become a community for others to not be afraid of being themselves and where they can embrace their differences.

DE: Which character in Golden Girls are you?

KK: Oh, hands down Dorothy! I feel like in my group of friends, I’ve always been the “mother” like figure. I just love her sarcastic, smart witted humor. She’s a classic.

DE: What’s your favorite fashion magazine?


KK: It’s not just a fashion magazine, but I love the indie magazine called The Messy Heads! It has everything from poetry, body positivity, and fashion. It’s the best magazine community, I’ve ever seen. I think more magazines should use their platform to build young teens/ adults.

DE: Where do you turn for fashion inspiration?

KK:I turn to old pictures of my Grandmother, she is a heavy influence within my brand. I like to think I’m the birth child of Twiggy and Jackie Kennedy. I love the big mod prints, with the structure of first lady chic.

DE: Who are some of your favorite designers?

KK: I’m obsessed with Emilio Pucci, I mea hello bold prints. Of course, Oleg Cassini is one of my biggest inspirations, since he created the “Jackie Look”. Lastly, Pierre Cardin, I love the futuristic and unusual designs he created in the 1960’s.

DE: What are your favorite ways to practice self-care?

By Danielle K. Hamlett

KK: Sometimes, I like to just shut down. I love the idea of once my technology runs out of battery, so do I. Everyday, I’ll charge my phone and once it dies, I take the time to write my thoughts down or use it to do a face mask. I also take the time to meditate everyday; it’s the perfect opportunity to clear my headspace. I used to think it would be impossible to meditate everyday, but now it’s my daily routine!

DE: Tell us about your intern. 😉

KK: My intern is the greatest, four-legged animal I could ask for. It can get lonely working from home from time to time. But my maltipoo, Concha forces me to go out to take her for walks, and keeps me company when I’m taking pictures. Even when I’m getting stressed out, she’ll force herself on my lap, and keeps everything light and fun. She can get lazy and takes plenty of naps through out the day, but she’s adorable so I let it slide.

DE: Finally, what’s your favorite breakfast food and why?

KK: I’m a firm believer that breakfast food is perfect for every meal. I also believe, that if a person chooses pancakes over a waffle that they should not be trusted. A waffle is the perfect, warm goodness that hugs syrups and melts in your mouth with every bite. I’m really passionate about breakfast foods.


Kelsey Keena is a 23 year old business owner and fashion maven. This past year she launched her brand, store, and blog. Be sure to keep your eye on the badass, feminist fashionista. Here’s her blog. To check out her Depop and purchase her amazing looks click here. To check out our Spring look book with Kelsey’s brand, click here. This is Kelsey’s instagram.