Hustle in Style: How Steph Major Became a Stylist to Jessie Reyez, Allan Rayman and more

Updated: May 5



Are you the designated stylist in your group? Do you dream of turning your passion for fashion and design into a full-time gig?


Steph Major is a freelance fashion stylist and consultant based in London and Toronto. She's worked with chart-topping artists like Shawn Mendes and Jessie Reyez, which has put her work at the centre of some of the largest red carpets and star-studded events.


How did she get there? We sat down with Steph to chat about her journey through fashion and the advice she has for up-and-coming fashion industry creatives.


Winslow: Let's start by you telling us about your journey to where you are today. How did you get your start in fashion?

Steph Major: As a kid, I used to love looking through fashion editorials in magazines. I spent a lot of time imagining what it would be like to become a"world-famous" fashion designer I even wrote it down as a career aspiration under my grade 8 yearbook photo. Fashion, art and design were big parts of my identity, but there was always some part of me that felt like that world was reserved for an exclusive class of elite people and that getting in being a part of it all was just a little too out of my reach. It wasn't until my last year in university that I took the time to self-reflect and ask myself what I genuinely wanted out of life. That’s when I decided, "okay, let's do this... let's follow your dreams" and I applied to a post-graduate degree at Parsons New School for Design. When I got accepted to the program and moved to New York that Fall, it cemented my belief that I was on the right path.

Towards the end of my degree, I got hired as a fashion assistant for Interview Magazine. Andy Warhol started the publication in the 70s, and it represented everything that I cared about in fashion: its history, stories and influences. Our days were filled with unpacking and organizing looks for upcoming editorials and arranging each piece by designer, commodity and colour. I had the opportunity to witness all of the magazine’s fashion stories take shape before me.

The first time I ever walked onto an editorial set I knew I wanted to be a stylist. Karl Templer, the creative director of Interview at the time, was shooting a fashion story with photographer Mikael Jansson. I was immediately enthralled by the shoot’s grandeur; the gowns, the colours, the music and the production design. I wanted to be a part of it. When I moved back home to Toronto a year later, I called up a styling agency in the city and asked if I could join their assisting roster. I had no idea what to expect. Eventually, stylists started giving me a chance to work with them. I paid attention to everything they did, from how they sourced looks to how they conducted a fitting to how they directed models on set. I took notes, asked questions, worked with everyone and said yes to everything. It was these collective experiences that became the building blocks of my career.

W: You've helped create looks for Canadian icons like Jessie Reyez and Allan Rayman. Can you describe what it was like to land those gigs and what it was like to experience that transition in your career?


SM: Back in 2016, when I started my freelance life, I was approached with the opportunity to style a music video for a huge Canadian hip-hop artist. I remember feeling incredibly nervous and unworthy of the offer. Although I had already been working alongside my friend Tiffany, who styles Shawn Mendes, this job was different. Not only would I be on my own, but I would be entirely responsible if things went wrong or if I couldn't deliver. Despite these initial fears, I said, "okay put my name into the list, and if by some dumb luck I get the gig, I will just figure it out from there." I kind of always threw myself into the lion's den, even if I was uncomfortable, I just wanted to push myself. Needless to say, I did not get chosen for that project, but after that experience, I hustled hard so that I would be ready for the next big one. Within a year, I met and started working with Allie X and Allan Rayman, two incredibly talented Canadian artists. Both of their styles were so different: Allie is this beautifully eccentric, high-fashion goddess who loves to experiment and push boundaries with her style, and Allan is this super relaxed, laid back guy who looks effortlessly cool in anything he wears. As artists, they each challenged me in their own ways and, as a result, taught me so much about myself and my ability to adapt and evolve as a stylist.


I met Jessie in 2018 when she was a rising star in the Toronto R&B scene, and I got hired to style her video "Body Count." The amazing thing about working in Toronto is that the creative community is tight-knit and so you end up being on set with a bunch of your friends who support you. The way everyone connects and works together is incredibly organic, and that's what it's been like with Jessie and her team, we instantly formed this natural trust and rapport with each other. We knew the same people, went to the same events and shared the same passion for Toronto’s growing music scene. After that shoot, I was hired to do another video and then another, and then one day, Jessie's manager called me and asked if I wanted to fly out to shoot a campaign with Jessie. We've been working together ever since.



W: Can you take us through the process behind developing Jessie's 2020 Grammy red carpet look?


SM: From a logistical standpoint, the process of styling a red carpet event like the Grammys can take weeks, if not months, to prepare. Award season begins around November, so dress samples are in constant circulation, in and out of fittings or put on hold for editorials or VIP clients. You have to make those requests far enough in advance to ensure you have enough options for your client. When it came to sourcing the right look for Jessie, I had to do a lot of research. I created a mood board of runway looks from designer collections that she could use as a reference point to my ideas. Once Jessie had a chance to look through the images and give me feedback on the silhouettes and styles she liked, I then was able to narrow down my selections. As a side note, when you are working with an artist, especially a musician, who thinks deeply and has so many layers to their identity, you have to consider their personality, their attitude and who they are as an artist when making any styling choice. Their music is telling a story that is often reflected in their style. Therefore, requesting one dress over another dress can be a monumental creative decision on your part. Ultimately, the brand or designer should be aesthetically in-line with your client's ethos.


At our fittings, we pulled an eclectic mix of edgier, streetwear looks as well as some statement-making glam dresses for her to wear to multiple Grammy week events and performances. Jessie's look for the red carpet was unique because it touched on a few interesting facets of herself and her music. We went with a romantic, crimson red, chantilly lace ball gown from Canadian designer, Romona Kaveza. Jessie instantly gravitated towards it at our fitting, which may come as a surprise to most people considering her uniform is an oversized t-shirt with converse sneakers... but when she tried it on for the first time, she said she felt like a kid playing dress-up.


One of the many things that I love about working with Jessie is that like the music she writes, she is open to pushing the boundaries and experimenting with her style, which gives me the creative freedom to try new things. After the award show, I was reading an interview where she said that attending the Grammys had been a dream of hers since she was a kid, so I think the dress in some ways symbolized that childhood dream coming to fruition; she had her very own“Cinderella” moment. I’m proud I was able to play a hand in that.

W: What's your favourite look that you've created so far?


SM: In all honesty that's a hard question to answer. Like most creative people, I’m often critical of my work and tend to either overthink things or spend way too much time procrastinating. As a result, I haven’t put one particular look into my own “Hall of Fame.” I would say, however, that any outfit which has either forced me to adapt myself creatively or has pushed a boundary in some way is the most exciting look to create. For example, if my client says to me, "here's what I own, what can do you with this? Or if they say, "here's my idea, how can you make it come alive?" and I’m able to deliver it beyond what they initially envisioned, that’s the most rewarding aspect of my job.


W: COVID-19 has heavily impacted creative industries. Can you describe what it's been like as a stylist working in the industry through this pandemic?


SM: Well, 2020 was going swimmingly until about March 1. I arrived back in London to the news that international borders were closing and countries were going into lockdown. The first week, I didn't feel much different, and that's because as a freelancer, there are bouts of time when your busy and sometimes when you're not. I slept in, binged watched a bunch of TV shows, caught up on my emails, worked on my taxes, etc. When week two rolled around, I began to feel a bit more anxious and was struggling to come to grips with the situation we were all facing.


One thing that's helped keep my anxiety down about my job is to only deal with the information I have in front of me, the stuff that's within my control. I have personally used this time as an opportunity to re-think my current business model as a stylist. I’m starting to look for new and interesting ways to modify and improve my skill sets and become more adaptive to a digitally focused industry. I’ve also been updating my website and trying to curate my social media content all while getting over my fear of making Instagram live videos. Unrelated to my job, I also learned how to bake, kind of.

W: In your opinion, how do you think the fashion industry is going to change, if at all, after COVID-19?


SM: I think there is a lot that needs to change after this. The biggest and most important of them, in my opinion, is a focus on sustainability. Historically, the fashion has been one the most wasteful, toxic and problematic industries - from environmental pollution to the exploitation of workers - it’s seriously ready for an overhaul. There needs to be a full and honest commitment to improve how the industry operates at the core. There is no reason why fashion can’t be comforting, escapist and mindful at the same time. We just need better solutions to get there.

Businesses should lead by example, repurposing unused materials and fabrics rather than buying new ones and making an effort to reduce their carbon footprint, where possible. I read an article recently saying that some designers are choosing to forgo multiple seasonal releases and instead focus on smaller core collections that can be purchased throughout the year, with limited quantity “drops”. I particularly love the “drop” model because it’s already a tried and true marketing tactic that a lot of streetwear brands use, and we also know that a sense of scarcity and necessity for a product makes it more exciting to buy.


For the individual consumer, sustainability might mean focusing on more balanced purchasing habits. Where we can, perhaps it means buying fewer but higher quality products from local or emerging sustainable brands. We are already seeing a wave of new, young consumers who are interested in companies with strong values and a clear social mission. Apart from that, we can also make a sensible effort to prolong the life cycle of our current wardrobe; repairing them when they're damaged or donating them when they no longer fit. No matter which way we go about it, it’s clear that promoting long term trends in fashion while sticking to sustainable practices can build a huge amount of brand value, employee and consumer loyalty as well as a more resilient supply chain that will endure the impacts of coronavirus for years to come.


W: What would you say to an emerging stylist who was just starting their career?

SM: These days emerging stylists have so much information at their disposal, most of them know what they have to do when it comes to the logistics: network, interview, intern, assist, create a portfolio. BUT the piece of advice I want to give - and I don't think enough people said this to me when I was starting out - don't be afraid to take risks and fail, and just trust the process.

"In the beginning, your career will seem uncertain; you might question yourself, you might fuck up along the way, you'll compare yourself to others and make some bad decisions. If that happens, simply acknowledge it, don't judge it."

Take that information and move on and remember it for next time. I am continually learning new things. You learn from observing and from doing, over and over until it becomes clockwork, and when you got that down pat, learn something new. If it seems crazy and unattainable, give it a shot anyway. You’ll thank yourself later when it all works out for you.


You can learn more about what Steph is up to on her website or you can follow her on Instagram.


Wanna see more of what we're up to? Follow us on Instagram, Twitter, or Facebook.

a community

Winslow Magazine

  • Facebook - Black Circle
  • Twitter - Black Circle
  • Black LinkedIn Icon