Name: Liisa Winkler, @liisawinkler

Years you’ve been modeling: Over twenty years.

Most notable jobs: Has shot for Gucci, Proenza Schouler, Ralph Lauren, Calvin Klein, Valentino, to name a few.

Define eccentricity. What does it mean to you? “Eccentricity entails a freedom to express who you are. It is sometimes used in a negative way, to depict a kind of craziness, but I think it is something that should be celebrated. It implies a confidence and understanding of who you are; an ability to take yourself lightly that seems to come most strongly with youth or with age.”

Has seeing your daughter get dressed inspired your own approach to style? “Absolutely, I love how she combines things with such freedom and playfulness. When she was little, she would go to school in creative tutu/plaid/ninja combos and pester me non-stop to wear all those mildly eccentric vintage pieces at the back of my closet. We both love pairing things that might not normally go together – sweatshirts over ball gowns, for instance.”

Is Stella a bit of an eccentric? Do you think most children are? “When she was little she was a total eccentric; I do think most kids are like this if given the freedom. My son loved to wear his sister’s dresses, skirts and hair accessories too! As she’s grown older, she has become more “safe” with her choices and worries more about fitting in with her peers. But I can see who she really is on the weekends when she is free to be herself, and that girl is fun!”

What is the most treasured piece in your closet? “At the moment I am super excited to wear my new multicoloured bohemian-type coat from Smythe.”

This shoot was wild to say the least. Was embodying this character a stretch for you? “No stretch. Just lots of fun! I love hats and headpieces but its hard to find the right occasion to wear them. There were so many cool ones on this shoot, poor Juliana, the stylist, couldn’t get me to stop accessorizing. Eventually she just said ‘So, which hat are you going to wear with this one Liisa?’”

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Did your time on set influence your personal style or prompt you to try new things? “It reinforced the idea that fashion should be fun and is about taking chances. You can never have too many hats, and the right outfit actually has the power to make you feel a certain way.”

What was your favourite look from the shoot?  

“The green vintage marching band jacket that Stella wore! I Love how it was paired with something pretty on the bottom. Also, my spiky paper unicorn-style hat…the colours were amazing.”

How would you describe your go-to fashion uniform? “If I am meeting clients, I usually go simple with jeans, some sort of shirt or tank and oversized blazer, maybe with my Converse or a cowboy boot.”

What is the best style advice you’ve ever been given? “Don’t be afraid to wear your favourite dress. Wear the crap out of it and wear it with everything! Also, wear what feels right, not what everyone else is wearing.”

Your most memorable fashion faux pas? “When I was 12-13ish, I was partial to a fluorescent green turtleneck and brightly hued harem pants (not proud).”

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Are there any trends you’ve tried to embody, but simply couldn’t make work? “High waisted pants? Never gonna work on me. I look like a giraffe! Very glad that’s over(ish).”

What has been your most adventurous outfit to date? “I’d have to go with my fluorescent harem pant phase, complete with spiral perm and headscarf obviously.”

Do you have dual style personalities when dressing for day vs. a night out on the town? Perhaps work vs. real life? “Not so much day vs. night, but definitely summer vs. winter. I feel pretty creative, inspired and free in the summer. I wear a lot more prints, vintage dresses and accessories. Winter dressing means a lot of layers and less freedom, the objective being warmth.”

Who is your eccentric style icon? “Growing up it was Lisa Bonet. I wanted to be her! I loved how she took chances and played with fashion, but it was always a cool reflection of who she was. (Perhaps it’s where I got my hat and headscarf obsession?).”
With your exposure to the industry as a model, do you find yourself growing more or less adventurous in style? “[Working] in the fashion industry does inspire a more adventurous wardrobe. You are immersed in an atmosphere where individuality is celebrated and you work with such inspiring and creative people. Absorbing some of it is inevitable!”

Can an eccentric look ever be too much? How can you tell if its gone too far? “You still have to be able to find yourself under there. It has gone too far if you stop seeing “you” and only see the outfit. Clothing should always enhance who you are, never cover it up!”

Best place in Toronto for fab fashion finds: “I love Vintage shopping. Kensington Market is good, but I also love hunting through small town thrift stores & Value Villages.”

READ MORE: The ultimate guide to wearing a hat this season

So many eccentrics swear by vintage fashion. Why is eccentricity so deeply rooted in the past? “Vintage is great because it is so individual. You can truly find a unique piece that expresses your personality. Vintage fabrics and designs often seem eccentric as they reflect past trends. You end up dressing out of another era, which is exciting.  Every item is different and tells a story. It adds a childish excitement, sort of an adult version of playing dress up, imagining the type of person who once wore each piece.”

Watch Liisa and Stella Winkler in action in our September fashion shoot

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