Industry Interview - Celebrity Stylist Kylie Gelfand
An early career pivot away from sports broadcasting is proving incredibly successful
Kylie Gelfand has always loved sports and did everything she possibly could to become a sports reporter. After grad school she was given the opportunity start her career at Fox Sports only to realize the work as production assistant wasn’t exactly what she had in mind. Through some soul searching and trying out new things, she landed on her current career - styling for professional athletes. With a big personality and some elbow grease, she’s secured a solid roster of NFL clients and is making a name for herself in the league. This is her story.
Nick: Kylie! Welcome and thanks for joining. You initially pursued sports broadcasting. What led you to go down that route and what sparked the shift to styling?
Kylie: I was born and raised in Oregon. When I was in high school I was trying to figure out what to do professionally, where I wanted to go to college, etc. It was always my mom’s dream to become a sports reporter but life had other plans for her. I grew up in a huge sports family and I didn’t want to sit in a cubicle all day, so I decided to pursue sports broadcasting and threw myself at that goal. I had internships during the school year and every summer while I was at the University of Oregon. I graduated during peak Covid in 2020 in a time where there was obviously no sports going on. I knew I didn’t want to go to a local news station and work my way up because I always dreamed about being the next Charissa Thompson, who joined Fox and climbed that ladder. So I decided to get my master’s in Sports PR from Syracuse so I could be more experienced and eventually got a job at Fox Sports! I was working in the highlights department where I cut videos and typed edits all day. I was so thankful for the opportunity but it was NOT for me. So I left and started figuring out what to do next. I had a few social media jobs (one was in beauty) and couldn’t stand that either. I soon realized that I wanted to be my own boss and do something that gave me flexibility and the opportunity to travel. I woke up one day and just told myself that I would start styling athletes with ZERO knowledge of how this worked.
Nick: So what did starting out look like and how did you finally start booking high-profile clients?
Kylie: I was constantly styling my guy friends. I would go to Nordstrom, buy pieces, have my friends wear them and do a photoshoot with me, and then return those clothes and do it all over again. I wanted to get as much social media content as possible so that when I reached out to people, they had a very clear picture of what I could do for them. I did that for months and that’s when I locked in my first NFL client. Once we got connected I offered to style him for free for the entire season. It feels like everything snowballed so quickly and the impostor syndrome started to creep in, but I genuinely feel that this is what I was supposed to be doing. I eat, sleep, and breathe fashion now and I love it.
Nick: You put in the work! Even though it happened faster than some of your peers, that doesn’t mean you don’t deserve it. Remember that. Tell me about your first NFL client and what it looks like to secure more of his peers or other celebrities.
Kylie: My first client was Stone Smartt. At the time he was playing for the Chargers so he was in L.A. already. I styled him for free with the intention of getting the content of him walking through the tunnel in order to build my own brand. Because he was my first big name, that content was extremely valuable. Every single week I’d drive four hours roundtrip to bring him clothes to his apartment near the Chargers training facility in Laguna Beach. The tunnel has turned into a red carpet so a known entity wearing something from your brand turns into a crazy amount of brand awareness. Then I started reaching out to friends of friends in the league, people who played football at Oregon, etc. I figured giving them one free consultation will get me in the door and have them want to work with me. I help my clients build beyond the football field.
Nick: That’s awesome. It’s also very clear how the flywheel starts and continues - one free session, then you get more press/notoriety, that gives the client’s brand positive momentum and you get more clients. I love it. What happens when your vision clashes with that of the client?
Kylie: What I tell all my clients when I start working with them is that I’m not looking to change your style, I’m looking to enhance your vision so what you put on looks even better than it did before. Above all else, I just want to make them feel comfortable. Unless I feel incredibly strong about a piece or an outfit, I’m very flexible around their opinions. I’ve had some very picky clients that I’ve had to go around and around with before we land on something, but I’m always prepared. Sometimes I’ll go into someone’s home with 20 different outfits so we don’t run into a situation where they try on everything and they don’t like any of it. But I’m also good at figuring out what they like so after the second or third time I style them, I know exactly what they want and that builds trust too.
Nick: I love that you have the flexibility in your vision for them. You’ve mentioned that you enjoy working with smaller brands and getting to boost their awareness. What’s your process for finding them?
Kylie: Because of everyone I followed and the content I engage with, my entire algorithm is men’s streetwear. So all those ads these brands create come directly to me. Occasionally I’ve have brands email or DM me but I’ve done tons of cold outreach. Initially I was doing 20-30 a day to build those relationships but that’s scaled down to 5 a day now. For the mid-sized and bigger brands I have my assistant reach out to the PR contact, but even with those we have a pretty solid response rate. I’m only reaching out to the ones that resonate with me and they’re always incredibly thankful. Plus the prices are much more reasonable.
Nick: I’m also pretty deep in the niche streetwear brands on Instagram so I totally understand what you’re saying. I’m sure there are still plenty of athletes who want to flex with the LV’s of the world but it’s really interesting to see the athletes become more brand agnostic. Before we wrap up, where do you see your business KYStyled in the next 5-10 years?
Kylie: I want to manage a full team. I have an assistant but I want more stylists under my company. This upcoming season is going to be very hectic because I have a lot of clients on teams in different cities. One day I’d love to be able to delegate employees to work with different athletes but still have the final say and have them understand my vision for style. Eventually, I would love to have a full showroom in L.A. and be able to work with more big clients and large brands. My passion for what I do and who I work with drives me, and I’m truly looking forward to expanding my brand and building lasting, impactful relationships. So the key word for my future is growth.