How independent fashion label Cakeworthy leans on nostalgia while investing in the future of their business with Square for Retail

Cakeworthy, an independent Canadian fashion label designing unisex streetwear apparel and accessories, was founded in 2014 by educator turned entrepreneur Brandon Shedden. With designs inspired by the bright colours and imagery of pop culture, the brand started out with Shedden using an at-home craft screen printing kit and selling handmade t-shirts on Etsy. Now an international lifestyle fashion brand that collaborates with some of the world’s top licensors, Cakeworthy creates clothing that celebrates bright colors, bold prints, graphics and 80’s and 90’s nostalgia. Here, we speak to Shedden about Cakeworthy’s rapid growth, his decision to open up brick-and-mortar locations, the importance of rewarding loyal customers and how every Cakeworthy item is designed to be “an Instagram post just waiting to be captured.” Note: Cakeworthy was offered free processing as compensation for their endorsement.

On Cakeworthy’s Cinderella story

I’ve always been pretty creative. I was working as a teacher, but in my spare time I started screen printing some t-shirts to sell on Etsy. To be honest, I had zero expectations that this hobby would become an actual revenue stream that would see me leaving my established career to pursue. Cakeworthy’s success was a happy accident, a real kind of Cinderella story. I started seeing a huge response to the products, and it really made me think that we might actually have something here. It would have been the safer choice to stay teaching, but I’m glad I took that leap, because ultimately it was the right decision.

When I started out, you couldn’t really find pop culture apparel in retail stores like you can today. I think what makes us stand apart from the giant fast fashion licence collaborations is that we only work with brands that we love and are obsessed with, and that allows us to focus on fan service. We really see through the fan’s lens when we create our products, and we operate under the belief that people want to have fun with their clothes.

On working as a team and Cakeworthy’s company culture

One side effect of rapid growth for Cakeworthy is that the team has also grown very quickly. In the beginning I was basically doing everything myself, but now we have people in marketing, design, a team in the warehouse, and our retail shop team. I always say, I am nothing without my team. We are all weirdos, and we love all of the same stuff. I joke that we are like the Land of Misfit Toys. We are the complete opposite of corporate, and I think we’ll always be a small business at heart, regardless of our financials. Every team member contributes to our success, and everyone’s free to chime in with design feedback or product inspiration, whether they work in marketing or in the warehouse.

The vibe at Cakeworthy is very chill. To the point where a new employee told us she was leaving her house and her mother said: “What are you wearing? Are you joking?” Because we had told her that we all wear sweats and she’d be overdressed if she got more dressed up than that. We were recently going to a licensing expo in Las Vegas and I told the team: “Everyone’s going to be in suits. We are going to wear OUR clothes.” I wanted us to wear our designs with pride, and it couldn’t have been a smarter decision. We got so much attention! People wanted to know where they could get the clothes.

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On creating ethically produced clothing

Something that has been very important to me from the start is making sure our clothes are ethically produced. All of our factories undergo international labour standards audits. We don’t want our clothes made anywhere that uses child labour, or pays unfair wages, or ignores environmental and health and safety codes. That way our customers can feel good about buying from us instead of buying some generic pop culture t-shirt from a massive retailer who isn’t too particular about factory standards.

On the decision to open a bricks and mortar store

I always kind of had a pipe dream of opening up a physical shop. During the pandemic we opened two different pop-up shops at our warehouse, and they were unbelievably successful. People were lining up at 5:30 AM! Before that I did not think anyone would come, and then there was this huge line of people around the building! The success of the pop-ups really gave me the push to think that we could actually pull off opening a retail shop, which we did, here in Hamilton, in October 2022. The response has been amazing, and our local clientele are so diverse. All ages, all demographics, it’s really cool. The great thing about Cakeworthy is that everyone’s a fan of something!

One day, I’d love to open up another store, maybe in a really heavily populated area. But for now I think it’s important for us to take a breath, take a step back and really appreciate the milestones that we are hitting.

On how Square for Retail helps Cakeworthy operate efficiently and reward loyal customers

I don’t have any formal background in business, and when it comes to figuring out business stuff, the fewer barriers I have to run into, the better. When we first opened the physical store we needed to choose a POS, and I’d had positive experiences using Square Reader back in the day. Once I learned about all of the features and integrations I could use I thought “Okay, Square is going to make my life a lot easier.”

Everything is so user-friendly, and so intuitive. The staff at our retail store were trained in no time. We use Square for scheduling staff, to manage inventory, and of course, taking payments. It’s so great to have everything in one place — the staff can easily use the Retail app to switch shifts or book vacation, we can look at sales reports at a glance, check on the inventory. Using Square for Retail has been an impactful time-saver for all of us, and we are definitely experiencing cost savings by not having to use different apps for every feature. With Square for Retail, the combined cost savings and efficiency make perfect sense for our business.

I especially love the loyalty program. I think it’s so important to reward loyal customers. As a consumer myself, I want to be rewarded for shopping somewhere! If I know I’m going to get coffee from Starbucks everyday, I am absolutely going to participate in their loyalty program. I want Cakeworthy customers who shop with us regularly to know that they are getting the best bang for their buck. And they love it — our loyalty customer percentage is higher than our non-loyalty percentage.

On being an “Instagrammable” brand

We always say that our clothing is an Instagram post just waiting to be captured. Our clothes are perfect for a visual medium, and our customers get really excited to share their purchases with their friends, or, in the case of some larger scale content creators, their followers on social media. I think that’s really contributed to the success of our brand. We get tagged in some pretty wild posts — recently Joey from NSYNC was wearing our clothes at some meet and greet and our fans were quick to let us know about it. And a contestant from RuPaul’s Drag Race recently wore one of our Golden Girls products on the show, which was so cool and such great exposure. It’s worth noting that most folks who rock Cakeworthy ‘fits are looking to get noticed. If you want to blend in with everyone else, we are probably not the brand for you!