I’ve always been obsessed with shoes! And for as long as I can remember, heel boy, located at 244 Princess Street has been the place to find a pair that are not only high quality but also on trend. The selection is always on point with brands I can’t find elsewhere. That’s why I was excited to connect with founder, Chloe Raincock, and learn a bit more about her shop.

Just under 30 years ago, Chloe was a recent Queen’s grad with a dream that she was able to achieve right here in Kingston. “My love for shoes and shoe shopping has been a part of me since I was young, and I always dreamed of opening my own shoe store. After graduating from Queen’s, I realized there was no better place to start this journey than in the university town I had grown so fond of—Kingston. It felt like the perfect community to bring my dream to life,” Chloe shares.

Ever since opening heel boy, the customers have been at the heart of what makes this dream come true so fulfilling. Raincock explains, “We love making people happy, whether it's fulfilling their footwear needs, helping them solve their style dilemmas, or being part of their special life moments. It’s incredibly rewarding to see our customers leave with a smile, knowing we’ve helped them find the perfect pair of shoes.”

Like many small businesses in 2025, it’s getting harder to keep the doors open. Raincock admits these are the most challenging years she’s ever faced as a small business owner, “Right now, it's critical. The situation is dire, and the truth is, if we don’t get the local support we need, we may not be around much longer. Kingston is such a wonderful place to live, work, and visit, but without strong local businesses, it risks losing its vibrancy. The current climate has made running a business incredibly difficult, and honestly, it’s never been this hard. We’ve been here for nearly 27 years, helping Kingston find the perfect shoes, but without local shoppers, we won’t be able to keep going. We need your support more than ever—don’t buy from major online retailers, keep your money in Kingston and support local businesses so we can continue to be here for you. It’s not just about us—it’s about keeping this community strong and thriving. If we want to see a brighter future for Kingston, it starts with each of us doing our part.” 

Now more than ever it’s important to show up for our community and heel boy makes it easy to do that with a wide range of footwear. “We’re often asked who our target market is, and our answer is always, "everyone!" At heel boy, we strive to meet every footwear need—whether you're walking the dog in all kinds of weather, preparing for a big interview, heading out for dinner with friends, or dressing up for a prom, wedding, or exciting holiday. Our team is all about inclusivity and believes everyone should be able to wear what makes them feel their best.” Raincock shares.

And like many of the small businesses downtown, you can expect that extra touch of care when visiting. “When you visit heel boy, you can expect a dedicated team member who genuinely wants to help you find the perfect pair of shoes.”