Jonathan Simkhai had his a-ha momentfive years ago. “One of my girlfriends and I went out in the city and she ended up sleeping over,” he tells me, by phone from New York. “The next day I asked her to come with me to brunch.” Dressed in a cocktail frock and heels, she refused. “I had a shirt that was really oversized on her. I rolled up the sleeves and gave her a pair of grey boxer briefs. She put on her heels and earrings and said, ‘Wow, I feel cool.’” The two had a great afternoon. “She never gave the shirt back. That’s when I was like, I need to start my own line.”
One year later, in 2010, he’d done it. “I wanted to do something edgy—to stimulate and push women.” With that manifesto as his guiding vision, Simkhai has been rewarded with a spot in the CFDA Fashion Incubator program as well as racks at both Barneys New York and Hudson’s Bay, among many other retailers.
Granted, Simkhai was better poised for follow- through than most aspiring designers. At the time of his epiphany, he was already employed as the creative director of his uncle’s apparel company, which manufactured what his uncle calls “clas- sics.” Thanks to the family business, he grew up immersed in the fashion industry. In Grade 11, Simkhai leveraged that experience at Havana Jeans, a shop near his upstate New York home- town, where he soared from sales to buying and merchandising all before graduating high school.
“My mom was constantly asking me for my opinion,” he says. “That was where my voice was in the house and even in school—my teachers would ask me for fashion advice. I would guess their labels. They loved me for it.”
Simkhai went to Parsons but left after his first two semesters; he was impatient to work. His col- lection, while indeed edgy, embodies his pragmatism. While the designer does try to get women out of their comfort zones (crop tops for spring), he does so with the gentle nudge of a best friend helping you get dressed. He describes the woman he designs for as someone who “cares about art, fashion and music. She wants to take risks.”
She’s also “going places,” he adds. “She’s a hustler.” Signature Simkhai is all-purpose hot: The crisp patchwork denim, slick leather T-shirts and woven metallic shifts he showed for resort are a young creative professional’s dream work-meets- play wardrobe.
He’s still designing as the clever stylist who wants to give real-world clothes that extra kick. When a girlfriend inquired last year if he liked her outfit, Simkhai said, “I love it, but I wish the skirt were longer.” So for the past two seasons he placed hemlines just below the knee. “Selfishly, I think, What would I want to wear if I were her?” he confides with a laugh. As it turns out, he wants what women want.
1. Best Stay: InterContinental Carlton Cannes
2. Precious Possession: “My iPhone.”
3. Signature Spritz: “My friend founded the label Arquiste. I love his scent Aleksandr.” $185, Holt Renfrew.
4. Celluloid Obsession: “Sister Act 2.” I know all the words.”
5. Toronto Must-Taste: Terroni