With a love of vintage clothing and a knack for connecting people, Jennifer Dooley is making a mark on Calgary’s arts community

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Jennifer Dooley's Vintage Style



To say that Jennifer Dooley is stylish, artistic, passionate and a true dreamer seems like an understatement. A born-and-raised Calgarian, her love of travel was sparked when she moved to Scotland in her early 20s. To combat loneliness in her new surroundings, she took the opportunity to explore the community and discover hidden gems. 

Her passion for art and fashion also inspires her other projects, including Art House – All of Us Together, which aims to provide international networking opportunities for artists, and, most recently, Wonderland Vintage, a line of curated vintage fashions sourced during Dooley’s extensive travels.

We spoke with Dooley to learn more about her personal style, her love for travel and her dream vacation.

Vintage dress purchased in Newtown, Australia; vintage bracelet was purchased from Elizabeth Burton, a famed dancer in Vietnam during the Vietnam War; ring is vintage from Dooley’s mother; vintage camera purchased in Montreal at a second-hand store. 

How would you describe your personal style?

My style is a mixture of classic vintage, with fun and flirty elements of modern pin-up, and a love for texturized items such as hats, fur and delicate lace. I also enjoy wearing anything with polka dots, which I first became inspired by when modelling for a stylist named Polly Polka Dot in Sydney [Australia]. I absolutely love the colour red, as well.

What inspires your personal style?

I would have to say my grandmother, Katherine, who recently passed away. She had a true love for anything that was well made. This encompassed delicate jewellery, unique clutch purses, fine-tailored coats, antique furniture and china. She showed me that beauty is timeless. Katherine also passed on her sense of style to my mother, Dorothy, who has given me some of my favourite belongings, including housewares, elegant hats and a long suede 1970s-era, hourglass grey winter coat with fur trim. 

Vintage top purchased in Sydney, Australia; vest from Bebe; leggings from Garage; custom top hat from daquinohats.com; rings purchased from various stores at The Core.

How has your style evolved?

When I was younger, I worried more about what people would think and tended to follow more trends. It was when I first moved to Scotland that I discovered a love for fashion. I would spend hours roaming through the small European boutiques. Seeing the freedom that most European woman had with expressing their style and sense of femininity gave me permission to do the same. Living in Sydney also recently reignited that passion. The streets in Sydney’s Inner West are full of an eclectic mix of people who express their unique personalities with their clothing choices.  

Where do you think you get your love of travel?

I think it comes from my father, who spent his life living in places like New York and travelling as much as he could. When I was young, our family split our time between Calgary and Rome. I’ve been told my first spoken word was “gelato.” After being on a plane at three years old, the travel bug never really left me. 

What cities are you still excited to visit or revisit?

Berlin is on my list for next places to visit. I’ve learned that there is a unique and emerging artistic scene there. I would also like to go to more remote places such as Laos in Southeast Asia. I’d always go back to the places I have lived — Edinburgh and Glasgow and Sydney are the top places that still own a piece of my heart. 

Red dress (worn under skirt) and belt, both from Better on You; pencil skirt from Blame Betty; heels purchased in Sydney, Australia; vintage purse from her grandmother.

How would you describe your career?

I recently finished my Ph.D. in marketing for social causes and the use of Web 2.0. I run a marketing consulting business called DSC, which focuses on providing strategic marketing strategies to my clients, with an emphasis on creating social change.

On the days that I focus on my creative pursuits, you can find me anywhere from running around in an old barn with a camera around my neck and photographing local musicians to visiting local vintage stores to peruse retail opportunities for Wonderland Vintage. 

What does your typical day look like?

A typical day in my life has no specific recipe and I struggle with a nine-to-five routine. Truth be told, on most days I often work long hours, in coffee shops typing away on my computer and drinking chai lattes, juggling all of my pursuits and projects.

Vintage dress purchased in Newtown, Australia; multi-coloured jacket with fur purchased at the Market Collective in the East Village; rings and necklace from her mother; hat purchased in Sydney, Australia.

Your love for art is apparent in the projects that you do. What artists and art genres are you the most drawn to?

I adore street art. It was living in Sydney’s Inner West that brought this about, as the region is full of so many great works. I specifically follow Australian street artist Rone, French artist JR (who runs the Inside Out Project) and also recently stumbled across the work of Brazilian street artist Eduardo Kobra. I have to mention Juilee Pryor in Sydney, who helped to start the street art movement in the early 1990s. 

Who are some of your favourite artists?

In Calgary, the list of artists is endless, but specifically Bad Portraits artist Mandy Stobo, photographers I. M. Ruzz and Courtney Townsend, the fine art photography crew of SEITIES and artist Desere Pressey.

What would you consider your dream vacation?

Places that push me out of my comfort zone — physically, emotionally or spiritually. I love to explore new places that are different from my comfortable life at home. I thrive on experiencing new cultures, new foods and new artistic communities. 

This story was part of Avenue's free weekly Style Newsletter. Sign up now and get home decor and fashion information and advice in your inbox every Tuesday.

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