Kaylah Wilson, who channels her creativity through fashion styling, is steadily carving out a distinctive space for herself in the industry
Stylist Kaylah Wilson has always brought her soft and dreamlike essence to her fashion styling. As a young Toronto native with Jamaican roots, she is always striving to represent Black culture and heritage in the iconic looks she has helped put together. Her contributions to visual aesthetics have been filled with elegant, quirky and boundary-pushing notions of style.
Her talent has not gone unnoticed; she has worked on campaigns for InkBox, 4YE, FASHION magazine and many more major brands. She has been styling for some of Toronto’s popular music names and has helped create characters that listeners can believe in. She has also spent time extending her work specifically to her community of fellow Black creatives, bringing forth work that is both culturally important and visually necessary.
In this edition of #MCNWorkLife, Kaylah shares how she started styling and how she carved out a place for herself. She goes into detail about what it takes to love fashion and to try to work within the fashion industry. Her story is a reminder that working with the community is how we can create work that matters and will stand the test of time and the constantly changing scene.
What first inspired you to pursue styling, and how did you find your way into the industry?
While I was in school at Ryerson, now called Toronto Metropolitan University (TMU), I joined what was called Rad Mag at the time, which was a photography, interior design and fashion print biannual magazine. I started off in a social media role, and then eventually by the time I was in my last two years of school, I was the editor-in-chief.
At that time, I was doing a fashion minor while I was in school, and my major was business management program where I specialised in marketing. Leaving school, I decided to go into marketing.
School is so interesting because it conditions you to depend on what information you have and the expectations that have been put on you to find the best route to get a successful job. One that allows you to stand on your own two feet and support your family and yourself.
Towards the end of 2020, going into 2021, I was like, “I’m going to email a stylist that I admire, that I like, that I’ve seen her work, and just ask her if she needs help”.
Her name is Steph Major, and she is from Toronto but was in London when I emailed. At that time, she was the main stylist for Jesse Reyez, and even now. It all aligned because I emailed her, not really expecting anything. But she got back to me and offered me an opportunity. And that was definitely a huge turning point for me because I allowed myself to just reach out. And ask for what I wanted.
She ended up being a really great person and sort of my first mentor. She’s the first person I met who was really open with me and gave me resources.
What does a typical day look like for you as a stylist?
A typical day for me varies; there are different days like prep days, fitting days, shoot days, and wrap days, basically.
On prep days, I’m mainly focused on admin work. Whether it’s having meetings with a photographer, videographer or the producer, or we’ll have pre-production meetings discussing whatever the expectations are for the project. I’m maybe making a mood board, or I’m making a deck that outlines who the talent is and what they need. I’m figuring out what clothes and who I have to reach out to.
Sometimes that’s a prep day, and I spend my whole day just at my computer. On other days, I’m out the entire time, driving around to source clothing, whether that’s picking up items, shopping, visiting showrooms, or meeting brands in their private studio spaces or homes.
Shoot days can be up to 12-hour days. You’re getting to set and executing the project. And wrap days are usually building out my expense budgets and all the admin to ensure everybody gets their clothes back. There’s a lot of logistics and communications in this job. Honestly, I think that’s something that people don’t always expect or know about the job as far as styling goes. It’s heavy logistics, planning and being organised in your communication and administrative work.
Which is a big part, maybe just as much as being creative and having an interest in fashion. It’s about being able to do the job before set, on set and after set wraps.
How would you describe your styling philosophy or signature aesthetic?
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Very early on, I knew that fashion was something that had a sort of hierarchy to it and elitism that comes with it. And my own understanding of me entering the industry, I knew I wouldn’t have access.
Personally, I didn’t have the money or the relationship to get things that were recognisable brand names. I’ve always been someone who was really into repurposing clothes and shopping vintage and thrifting. As much as I’m in the fashion industry, I’m very mindful of the really harmful overconsumption and overproduction that happens in the fashion industry.
I thought I could combat that by primarily trying to source vintage and primarily trying to source locally. This allowed me to create a signature style that I didn’t even realise I was necessarily doing or had. Also, I think in addition to the sustainable mindset, I also love contrasting and colour blocking, and I love playing with textures and shapes. Which just came about naturally.
What are some projects you’ve worked on that felt especially fulfilling or meaningful to you?
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Most recently, I loved the shoot with Jorian; she messaged me to work on a project, and I was excited. The model Janine I met at a vintage store before, and she’s such a sweet person with an incredible spirit, a great attitude and mindset.
This shoot came together really well. I loved this 80s prom dress that I cut the skirt off of and turned it into a corset. It was this perfect thing, and then I put her in these black fishnet tights that had rhinestones on them. In the photos Jorian captured, it was as if her skin was glittering, which I loved.
Jorian is also Jamaican, and we’ve always connected over just doing things that are for our friends and our community of people because we feel comfortable. This also means we feel comfortable to experiment and do things that maybe we don’t get the opportunity to always do on other sets or other shoots.
One of my favourite images is a shoot with the model Dominique, who’s also a lovely friend. She’s wearing this blue vintage bodysuit that I sourced and these lace vintage bloomers. These beautiful green shoes feature crystal tassels on the tips and a stylish slingback design.
In my conversations with Téjahn, the shoe designer who was launching her new shoe collection. We talked about the styling and how we could launch the collection. Her clientele is all these Black women who are business owners and Black women artists who have a very distinct style and very distinct fashion taste. I thought, “How about we do an outfit that complements the shoe the same way that your clients do when they buy the shoe?” And she loved it, and we leaned into it.
How do you balance the demands of a busy schedule while avoiding burnout?
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I am still balancing what my perfect mixture of keeping myself refreshed and working looks like. I’ve always been interested in health and wellness, and I’ve leaned into that over the last couple of years. Especially as my work and my career have been progressing and I’ve been getting busier and working on bigger projects.
I am really into cycling, and you have to put all your focus and your energy into it so that I’m not just drifting off with my mind about all the things I have to do. Because I’m so present in the movement and the exercise and my surroundings, and where I’m going. I started running as well.
For a very long time, I would do a five-minute jog type thing or at the gym, or I’d be like I’m going to run around the block. Then a friend of mine was challenging me and asked if I could run 10k, and I ended up doing, I think like 12k.
That was a huge breaking point for me because I loved it. I felt amazing after, and then I continued to do that. It also strengthens my body because styling is a very physical and laborious job.
Something else that has helped has been having the gift and pleasure of having a mother who is very holistic and knowledgeable about nutrition. Especially knowing the role that it plays in your mental health and your physical health. Understanding food and nutrition lets me be equipped with knowledge that is really significant, especially as you get into adulthood.
Who or what influences your creativity the most?
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Law Roach is one because you cannot be a stylist, especially a black stylist, and not admire and acknowledge the trailblazer and talent behind Law Roach’s career. He is incredibly talented and has been very vocal about the misconception that barriers for Black people disappear once you achieve success — they don’t. He is one of the stylists who got so much attention for pulling archival and vintage, and he’s spoken on the fact that he did that out of necessity, but because he didn’t have access to big labels.
Another woman who’s also become one of my mentors is Vanessa Magic. She used to be a costume designer, and she kind of pivoted and is now more of a writer-director. She’s allowed me to step into film and into costume design in a way that has been pivotal. I did a short film for a music artist’s album called Debby Friday, and she created a visual film for her album. And that was one of the first projects that I took on. The film is called “Good Luck”, and it’s synonymous with the name of her album.
Additionally, someone I love is photographer Renell Medrano, she does amazing work. I look at her work and gain insights that relate to me as a stylist, whether it’s the use of negative space in some of her pieces. She also just does stuff for black people, and I love that. I really do want that to be a foundation that I will always come back to and always build upon. The opportunities that she creates for representation and that she creates for her community is really beautiful.
What advice would you give to someone aspiring to follow a similar career path?
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It’s always nice to be inspired by other people, but to try your best not to see someone else doing something and feel like you’re not doing that. You need to pay attention to what inspires you, and that allows you to keep moving forward in the direction that’s right for you. Everybody is different, and if we were all making the same kind of art, then that’s the opposite of the point of making the art.
Your personal lens which you view things, or the personal meaning behind the relationships maybe that you end up building, should shine through. If you focus on building relationships with people who genuinely connect with you, support you, inspire you, or whom you look up to and can learn from, you will create an amazing foundation of community. These connections will also help you gain a deeper understanding of yourself. That understanding, in turn, will set the stage for a successful and fulfilling career.
What do you hope your legacy will be both in fashion and beyond?
I’ve been thinking about it a lot. I’m unsure. There was a period of time when I felt quite discouraged in how much media we are consuming. I felt that we were getting lost in the ether, but I think that helped me to understand the impact that I wanted. I’m interested in creating work from a certain visual space, more so than in achieving a certain status of work. What I want to leave behind is connected to the people that are around me and the impact that I create for them. I’m also focusing on setting myself up business-wise and creatively to be able to offer opportunities to other people.
I would love — and I’ve been trying my best to work towards —having a bit more infrastructure surrounding what I do. So that I can reach my hand out and help someone else to do something similar.
It’s important that we are connected and that we allow ourselves to build something together as a community and through relationships. Because I think it’s so much easier when you have others surrounding you to do what you’ve dreamt of doing.
