Fancy Free: Jillian Wood of Headmistress

November 30, 2011

For this week’s Fashion in Canada post, I’m spotlighting Jillian Wood of Headmistress. Her completely covetable + fanciful designs are the perfect finishing touch to any winter ensemble!


Before we had Royal Wedding fever and a fascination with fascinators, the Toronto-based designer was busy quietly creating her whimsical collection of headpieces and accessories.

Wood designs statement-making velvet head wraps, turbans, feather-adorned rings and hippie headbands. These charming accessories — all made in Canada — mix modern with vintage for a look that harkens back to a bygone era, but still feels fresh and urban.

What is your favourite fashion memory?
“About a month ago, I walked out of my apartment onto Queen Street and I saw a middle-aged man with hair past his shoulders wearing a tank top with a tiger on it bike past me. He was wearing one of our feather headdresses. My friend later saw him walking and asked him where he got it since it was obviously Headmistress. He had bought it for himself from Frock on Roncesvalles. It was awesome because this guy had serious personal style and zero inhibitions, which to me is the essence of fashion. Plus, it proved to me that you should never think you know your customer inside and out, because just when you think you know, a monkey wrench like that gets thrown in there.”

What is your favourite fashionable movie?
“I’m much more of a movie ‘listener’ than a watcher, since I have trouble sitting still long enough to actually watch something. That said, I often work with movies playing in the background. I had never seen Annie Hall and I finally watched it last week. It’s a super relevant movie to rewatch for fashion these days. Diane Keaton’s androgynous look is spot-on, but if we’re being honest what I really love to watch while I work are masterpieces like My Big Fat Gypsy Wedding and Teen Mom. Quality television.”

What are your favourite sources of inspiration?
“The Canadian landscape and our shared history is very influential in my collections. We do a lot of feather pieces and I try to use as many local Canadian feathers as possible. For fall this year, we did an upcycled fur collection made from old coats. It’s particularly Canadian since our entire foundation is based on the fur trade. I like the idea of making pieces that are inspired by our backyard and are functionally wearable for our winters as well.”

What is your fashion maxim?
“I follow Coco Chanel’s one about taking one accessory off before you leave the house. I tend to dress fairly accessory-heavy, so it’s a good tip for not looking like you’ve lost it.”

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