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Meet Kaylynn Jaycox a Stylist with On Set Managment

Today we’d like to introduce you to Kaylynn Jaycox.

Kaylynn, let’s start with your story. We’d love to hear how you got started and how the journey has been so far.
I grew up in a small town in Wyoming, where my family didn’t have much but my siblings and I learned the value of hard work. When I was eighteen, on a blizzardy winter night, I packed up my 2000 Oldsmobile with all of my belongings—mostly just clothes—and drove to Dallas, Texas, with the goal of working in the fashion industry. I didn’t have a job lined up, I didn’t know a soul there, I didn’t know where I was going to live, and I had about $1,000 in my bank account. When I arrived, I went straight to the admissions office of The Art Institute of Dallas and asked if I could take classes, which started in just a few days. And then I got to work.

From 2009 to 2015, I worked in many different areas of the industry: wholesale, retail, design; you name it. I just wanted to learn as much as possible and find out what I was good at. But until the Chanel fashion show came to town in 2013, I didn’t really know what a freelance fashion stylist was or what one did. The show was a big deal for the city’s industry. Everyone pitched in to make sure things ran smoothly, and I really wanted to be a part of it. A friend of a friend was working for the show, as a stylist, and when I learned what he did, I knew that I wanted to do that too.

Before you can become a stylist, you need to work as an assistant stylist. So in 2015, I left my job working wholesales to sign on with On Set Management. In 2018, I took another leap of faith and worked to transition from assistant stylist to stylist. That felt like a big risk. It made me nervous because I had established myself as a top assistant, and for the first time in my life, I felt like I finally had a solid, steady, adult income doing something that I was good at. I also did not know if clients would want to work with me as a stylist, which involves a lot of skill sets that you don’t necessarily use as an assistant.

The year definitely started slow. I went to yoga classes a lot more days than I went to set during the first couple of months. But people took chances on me, and more work eventually came with time. And now, I feel very happy that I took all of those leaps of faith: moving to a strange, new city, leaving retail for styling, and moving from assistant stylist to stylist. I feel so fortunate to be doing what I do, bringing sets to life and making clients’ products look their best, and I can’t imagine doing anything else.

We’re always bombarded by how great it is to pursue your passion, etc – but we’ve spoken with enough people to know that it’s not always easy. Overall, would you say things have been easy for you?
Oh my gosh, no! It has been so difficult to get to this point, and I definitely ran into a lot of challenges. Working three jobs at a time, living on $40 for two weeks after I had paid my bills, sometimes not having money for food. It was so stressful.

I tripped myself up sometimes too. At a social event, years ago, I approached a local designer who I respected a lot and told her how much I admired her work, and she actually offered me an internship with her office. I was over the moon, and it was one of my best days in Dallas up to that point. After a few months of working for her office, the manager had asked me to cash some checks sometime between Friday and Saturday and told me I absolutely could not forget.

It was Halloween weekend, I had a big party that Friday night, I felt terrible the next day, and I completely forgot about the checks. They just sat in my glove compartment. Some of those checks were payroll checks, so on Monday morning, I got a call directly from the designer, understandably very angry, wondering what happened. People were waiting to get paid, and they didn’t that day because I forgot. She fired me about an hour after I got to work, and I was devastated. I thought I had ruined any chance of working in the Dallas fashion community and burned every bridge that I had built up to that point. But I didn’t give up, and I never made a mistake like that again.

So let’s switch gears a bit and go into the Stylist with On Set Management story. Tell us more about the business.
I am a stylist whose work is concentrated in Sets and Propping, Tabletop, and Interiors. So that means that I am usually responsible for “setting the scene.” Making the print or video advertisement come to life and look exactly like the clients pictured it in their head. When people hear “stylist,” they often think “fashion.” But that’s not the full picture. For past jobs, I’ve had to obtain 13-pound live bass fish to advertise fishing gear, buy 1920s gas pumps to lend authenticity to an old garage, and find the perfect athletic wear for a fitness photoshoot on the coast of Iceland (OK, sometimes it is “fashion”).

Basically, I have to find, rent, or buy things that no one in their life thought that they would ever need to get. And I want to do it, within a budget, in a way that brings life to the advertisement and the product. There’s an old saying that a stylist is only as good as her contacts. You want to know the best places to look, to stay ahead of the curve. I pride myself in maintaining an extensive list of quality contacts that can supply me with the perfect set pieces for almost any situation you can think of. In my free time, I scour stores, flea markets, and antique shops to fill my prop room with things that I know will be useful down the road. Also, I work hard to keep my contacts satisfied and maintain positive, close working relationships with them because they are critical to what I do.

One of my mentor when I was an assistant, once told me something that I will never forget: put life into anything you style. Fill the objects with life, think with movement, fluidity, and emotion. So step one is getting the stuff. But you can’t forget step two, and that’s creating something meaningful, that sends a message, through every job you do.

I still haven’t gotten used to walking into a store and seeing an advertisement that I worked on, on the wall, or opening a magazine that I love and seeing my work on the pages. It’s really satisfying seeing all of that hard work as a finished product. One of the first jobs that I did as a stylist was for a very large business. It was a big-budget project. More than half a year later; one of the people I worked with was visiting New York and saw our advertisement up in Times Square. I couldn’t believe it! I still had that same feeling when I recently saw some of my interior styling work in Architectural Digest.

I also love the places that styling has taken me, around the United States and the globe. I worked on a three-week shoot in Los Angeles, and in the last year, I did a job at the most beautiful home in upstate New York. More recently, I had the opportunity to shoot for a week in Iceland, which was a beautiful experience that I’ll never forget. I will continue to base myself out of Dallas and do a lot of work here, but I hope to build a more geographically diverse portfolio of jobs as my career progresses.

Has luck played a meaningful role in your life and business?
I’m sure everyone runs into a little luck, whether it’s good or bad, at some point in their journey to success. My mother always said that timing is everything. I am a big believer that success happens when opportunity meets preparation.

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Image Credit:
Manny Rodriguez, Matt Hawthorne, Will Graham

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