A Look at Heel Boy Waterloo

For April’s Community Cord column, I interviewed Chloe Raincock, Founder of Heel Boy, and Brie Heatherley, Marketing and Strategy Manager at Heel Boy, to learn about this season’s hottest trends.  Heel Boy is a shoe boutique in Uptown Waterloo, offering new shoes in the latest styles, for both men and women. While the boutique didn’t start in Waterloo, it’s a welcome addition to our fabulous and up-and-coming community!

Here’s the inside scoop on this shopping destination.


Can you give me a brief history of Heel Boy.

Chloe opened her first of four stores in 1998 in Kingston, ON.  Heel Boy quickly became the “it boutique” for shoes as the collections each season are a perfect balance between trendy, casual, formal and unique styles. Since then, Heel Boy has added two locations in Toronto and one in Waterloo.

What does Heel Boy love about Waterloo?

Heel Boy loves the community and support of Uptown Waterloo! The sales staff love the neighbourhood and how they are so close to so many delicious coffee shops!

Where do staff members love to hang out in Waterloo?

Jane Bond, Death Valley’s Little Brother,  and Honey Bakeshop.

What can customers expect when visiting the store?

Knowledgeable and dedicated sales staff will help customers find the perfect pair of shoes or assist with any shoe dilemma.

What’s unique about shopping at Heel Boy?

Heel Boy has a diverse collection of shoes, with something for everyone.  This is especially true now that men’s styles have been added at the Waterloo location.  Heel Boy Waterloo has a welcoming atmosphere and offers customers a positive shoe shopping experience.

How does Heel Boy decide what brands to offer?

Heel Boy offers brands that represent quality and style at respectable price points.

Inspiration for the buyer?

West Queen West street style are a huge inspiration for the shoe collections offered.

Three words to describe the atmosphere at Heel Boy.

Friendly, knowledgeable and dedicated.

What sorts of events, shows, etc, does Heel Boy participate in Waterloo.

Heel Boy cares about community. Recently the shop participated in Heels For Hope, helping the Canadian Cancer Society raise more than $12,000!

Heel Boy Waterloo

What are the upcoming shoe trends for Spring?

The platform is back in a casual flat or tall chunky heel.  The mule is making a major comeback in an easy slip on peep toe or with a 4” heel.  Any shade of blue is hot, especially periwinkle, as well as floral prints.  Athletic style shoes are also a popular trend.  New Balance, Keds, Lacoste and Sperry are all brands that offer different colours and styles, perfect for everyday wear.

Any style advice related to shoes specifically?

Most of this season’s styles are quite versatile. Any trend can be worn with jeans or casual cropped pants, skirts or dresses.  Choose a bright coloured shoe to add interest to a basic outfit.  Choose a short heel (1”) instead of flats which are just as comfortable, but will elevate your look.

Anything else you would like readers to know about Heel Boy.

Heel Boy now has a prominent presence online as heelboy.com (currently receiving a makeover) and the store on Shop.ca continues to grow.

Be sure to get a copy of April’s Community Cord for the full story!

Happy shopping lovelies.


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