This Friday, GRAMMY®-nominated artist Charlotte Day Wilson will take the stage at Toronto’s Roy Thomson Hall for a one-night-only performance with the Red Bull Symphonic. Following the release of her sophomore album, Cyan Blue, Wilson continues to bring a new depth to her sonic landscape by blending her signature sound into the context of a full symphonic orchestra.
Like every artist with a strong creative presence, Wilson has a signature look—it’s androgynous, refined and often monochromatic. To elevate the principles of her everyday style, Wilson enlisted the help of Literary Sport‘s Creative and Design Director, Jackie McKeown to style a look for her stage performance this Friday.
Ahead of the show, we stopped by Wilson’s fitting at Holt Renfrew on Bloor to chat about her everyday uniform, choosing the perfect outfit to perform in, and her love for the zip-up hoodie.
SG: What is your everyday uniform?
Charlotte Day Wilson: “I think I generally gravitate towards more athletic things. I usually feel most comfortable in some version of elevated athletic wear. I always feel good in that.”
Who are some of your favourite designers?
“I think WANZE is one of the best designers in Canada—her clothes are amazing. In terms of other designers, I wear a lot of Maison Margiela. I love LEMAIRE. I also rock a lot of Stone Island.”
What was the inspiration behind your suit for the Grammys?
“It just felt right in the moment. It was a nice opportunity to dress up and try a suit, which I never really do. I think it can be hard to do well sometimes, especially for a more masculine-presenting woman. I didn’t want it to come across as too masculine. I feel like we struck a nice balance—somewhere between feminine and masculine, but still strong. I felt comfortable in it. It made me feel confident on the red carpet.”
What do you wear when you want to feel confident?
“I always gravitate towards something more loose fitting—that’s how I feel the most confident. I feel like when I have the space to just sit or stand, and not fuss over how my outfit is sitting. That’s when I feel the best.”
What makes a good airport outfit?
“My number one rule for an airport outfit is a zip-up hoodie. You’re going to be cold getting to the airport, but as soon as you get there, you’re going to be hot—so you need to unzip. Then, once you’re on the airplane, who knows what the temperature will be, so you need that versatility. I usually go for cargo pants because the pockets clasp, so you feel safe putting your passport in there. And I like to wear one or two things that make me feel cute. I want to still look good at the airport—you never know who you’ll see or who’s looking at you. So I keep it balanced: not trying too hard, but putting in a little effort.”
Do you have any special mementos or good-luck charms that you wear?
“I like to wear my grandparents’ rings. My mom tends to give them to me in big moments—she passes down these heirlooms when something significant happens. I’ve learned to channel the strength my ancestors have given me. Sometimes, when I’m feeling down on myself or overwhelmed by pressure, or things aren’t going how I want them to—I remember that my ancestors worked very hard for me to be where I am. Having their rings on my body is a good reminder.”
How do you choose the right outfit to perform in?
“For me, the performance outfit is a little different than what people might expect. The biggest thing for me is to wear a flattering silhouette. Everyone’s body is different. I happen to have one where I like to accentuate my waist and have more volume at the bottom of the pants. That’s my general rule of thumb.”
What will you be wearing for your performance on Friday?
“I’ll be wearing a full look by Max Mara.”
What made you choose this look?
“The moment I put it on, I just knew the silhouette worked perfectly for the moment.”
Who are your personal style icons?
“I’m not going to lie to you—I don’t. I think especially as a lesbian who falls somewhere in between masculine and feminine styles, we’re kind of making it up as we go. I take most of my fashion inspiration from menswear—we’re mostly pulling from the men’s section in Holt Renfrew today for Friday’s show. Finding ways to incorporate men’s clothing into my style that still works on my body is a challenge, but it forces me to dress in a way that’s unique to me.”
What is your favourite or most worn item in your closet?
“Honestly, it’s the zip-up hoodie. But cargo pants are a close second. If I don’t know what to wear or if I’m in a hurry, I always throw those on. It always works.”
