Setting the Tone: How Harry Rosen Innovated Their Digital Experience During the Pandemic


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From NBA Champions to Prime Ministers, luxury menswear purveyor Harry Rosen has dressed Canada’s most stylish men for three generations. Created in 1954 by its namesake founder, the iconic retailer has become synonymous with sartorial excellence. 

Like many businesses, the 2020 pandemic forced Harry Rosen to think out of the box and pivot quickly. As physical retail businesses were forced to close doors or operate at a limited capacity, the team at Harry Rosen tasked itself to quickly deploy a strategy that harnessed its digital platform to provide an innovative shopping experience. Here, Ian Rosen (Vice President, Digital and Strategy) shares his thoughts on the new wardrobe for men, digital innovation, and the brand’s latest campaign, Set the Tone.

What does style mean to you?

Style for me is in the details. It’s about being thoughtful about each and every part of the way you’re presenting yourself. Since I was really young, I’ve obsessed about the way my jeans fell over my sneakers or the way my collar stood under my suit jacket. Ultimately, it’s these little details that I find help you project yourself with confidence. Ninety percent of the time you’re the only one who notices them, but they help you feel complete in what you’re wearing. Style should also be equal parts making a statement and feeling comfortable. If you aren’t comfortable in what you’re wearing, and become self-conscious about your outfit for an entire evening, you’re letting the outfit wear you.

What is the most treasured item in your wardrobe? 

I love shoes. I think I have more brown dressy and casual boots than I have places to keep them in my closet. Two years ago I got a pair of brown suede Brunello Cuccinelli boots and I could basically wear them every day. They have a removable buckle that can change the look and they dress up with a sports jacket or down with jeans. I find that all of my most treasured items are the ones I get the most mileage out of.

What excites you about the world of menswear?

The shift towards a more casual dress code at work opens up so many possibilities for men to develop their personal style beyond an industry uniform. Getting dressed for work also just got a lot harder! A white shirt, navy suit, and black shoes might be less comfortable than casualwear but it is incredibly easy. The new work wear is much more nuanced; men are going to need to invest in new wardrobe staples like dressy sweaters (swackets), collared-knits, overshirts and even work appropriate t-shirts. This isn’t about re-purposing your gym shirts. Classic categories such as sports jackets and dress shirts are casualizing as well; fabrics are becoming more technical and traditional tailored silhouettes are evolving to have softer shoulders to pair back to denim and more casual outfits.

What is a style law that you will never break? And conversely, what is one that you believe no longer applies?

When you wear a belt, it needs to pair back to your shoes or your outfit. Never wear one tone of brown on your dress shoes and another on your waist. To me, this is one of those little things that sets the tone for your entire outfit. I’ve seen so many nice suits ruined by mismatched tones. For a rule that no longer applies, I would say you no longer need to think about a suit as a single outfit. The trend towards brands selling suit separates (jacket and pant sold separately) have given permission to think investing in a suit differently. Can the jacket be worn with a casual pant? Can the pants be paired back to a bomber jacket or a heavy sweater? What historically would have been something that you could only wear for business and special events just got a lot more versatile.

COVID-19 has forced many of us to work from home and restructure our wardrobes. How has your style changed as a result?  

Working from home pushed everyone to reassess the way they looked at their wardrobe. In speaking to many of our clients and peers, there are two big things that have become of utmost importance: comfort and easy care. I’ve been heavily focused on pants with stretch in them (for comfort) such as the incredible selections from PT01, Paige, and AG, and I’m also ensuring I have a core set of shirts and sweaters that are easy to take care of at home. Fashion is changing to be more dressed down but one thing isn’t changing, which is it’s important to get dressed for your day. My biggest tip that I give to everyone is to designate a pair of indoor sneakers—especially if you wear orthotics like me. They help me feel like I’m at the office a little more than a pair of slippers. 

Ian Rosen in sports jacket, sweater and pants leaning against coffee table
Ian Rosen; Vice President, Digital and Strategy (Photo: Harry Rosen)

What are the core sartorial essentials that you think every man should have in this new landscape and work culture?

The Sweater Jacket (Swacket) is a must have. It’s basically a more formal sweater and is perfect for working around the house but can easily be worn at the office or for a night out. I also think today’s man should be thinking about rebuilding their casual pants wardrobe. Whether it is a pair of dressy drawstring pants, or a pair of chinos with a ton of stretch, there are so many options that bridge casual and dressy in a really tasteful way. Finally, a thin layering vest is a great way to elevate a long-sleeve t-shirt or knit without having to put on a sports jacket.

Many men are also juggling fatherhood with working from home. As a new father yourself, what is the best advice you have for dads who want to maintain a sense of presentation as they look after their kids?

On the second week of quarantine I decided to get dressed up in dress pants and a sports jacket for an important video call… only to find myself covered in spit-up later that day! I learned my lesson quick—my work-from-home wardrobe is 100 percent easy care from brands like Fradi, Patrick Assaraf, BOSS and Maurizio Baldassari where I can throw myself in the line of fire without hestitation. With Ella now crawling and on the move I’m also investing in a lot of tailored sweatpants and joggers so I can drop to the floor without tearing through an inseam.

RELATED: 8 Canadian Entrepreneurs Reflect on Fatherhood and Their Fathers

Harry Rosen just launched its new platform, Set the Tone. What does setting the tone mean to you? 

Set the Tone perfectly encapsulates why we’re in business: to help men go out and take on what’s in front of them, personally and professionally. For me, the platform speaks to the fact that when you feel your best, you do your best. This rings especially true in 2020 when we’ve seen so many people pull together in the face of such unprecedented times. This platform isn’t about clothing—it’s really about the people who wear them.

With this new direction in mind, what do you think makes an exceptional brand in today’s landscape? 

To be an exceptional brand you need to stand for something that people can relate to and do that consistently. Today’s consumer is looking for brands to connect with—whether it’s their local coffee shop that they tell everyone about or the restaurant that knows their order before they sit down at a table. This brand platform gives us a new way to connect to our loyal clients and also build relationships with new ones. We’ve opted to use many Role Models instead of Fashion Models in many of our Fall/Winter content because we know that great stories are what people are looking for right now. Whether it was our feature on Matty Matheson (legendary chef) or Nick Kypreos (Former NHLer, sports analyst, and entrepreneur), each story showed great people doing great things, who also have a passion for fashion and style in their unique way.

Collage of chef Matty Matheson getting a custom suit made
Harry Rosen Role Model Chef Matty Matheson (Photo: Harry Rosen)

How have you been able to use 2020 as an opportunity to learn?

Without a doubt the entire situation has been challenging for our business, but we have so many bright spots that make me confident we will be a stronger company and a better place to work in the future. Most importantly, we have seen just how much our people can accomplish when they are empowered. Whether it was watching our team launch a new website in six months (it would traditionally be a 10-12 month project) or a group of cross-functional leaders totally reshape our company point of view on diversity and inclusion—when we gave our people permission to run with the ball on key strategic projects, they blew away even our highest expectations.

Another highlight was how creative our team got when our back was pushed against the wall. How do you fulfill record-setting e-commerce orders when your stores are being shut down? How do you bring the best of the store to a client’s home over video if they don’t feel comfortable coming into the store? How do you keep close to 900 associates up to date with the safety protocols we’re putting into place to ensure we keep them and customers safe? We found a way each and every time to solve the challenge we were facing. So many of the solutions we’ve put into place will remain long after the COVID-19 situation is behind us.

…when we gave our people permission to run with the ball on key strategic projects, they blew away even our highest expectations.

As the lead on the e-commerce platform, what are some major trends and observations you have made about consumer behaviour?

People want a personalized experience, which is why we’ve partnered with leading technology companies that ensure that the web experience for one clients isn’t the same as the next. Based on the products browsed or their previous purchases, we can start to tune our experience to ensure we’re not showing them products they wouldn’t be interested in. This is exceptionally hard for new clients who arrive on the site, which is why we recently launched a style quiz that allows a client to share their preferences with us. Our site is immediately personalized for them! You can take the quiz to find a perfect blue dress shirt or a new work-from-home outfit, and we see clients really loving the conversational experience. People also want speed. There are so many studies about how many customers you lose for every second it takes your page to load. There ultimately are two ways of solving this: i) make your site lighter in content and imagery, or ii) use modern practices to meet the client’s expectations and keep as much rich media on the page as you want. Obviously, we chose the latter.

RELATED: Harry Rosen and Toronto Raptors GM Masai Ujiri Team Up to Support the Black Youth Helpline

How do you define innovation in the context of your business?

Innovation in our context is all about transformation the purchase journey for a client. Specifically, how are you placing the customer further and further in control of how they shop with you. How do they start a journey in-store and continue that online, and vice-versa. We’re focusing everything on the idea that we need to eventually service so many different journeys with digital tech at the centre of it, but we don’t really want technology to be the focus—we need to keep the focus on the exceptionally curated clothing we sell. As an example, so much of our business is driven by our store-based clothing advisors, who are trusted style advisors for so many of our clients. We built them a tool that allows them to curate personalized selections for their clients off our website where they can choose the products and even the size for a client and share it directly with them over text or email. The client can add to cart and purchase in just two clicks. This is us taking the traditional journey of a client coming in to visit their trusted clothing advisor can happen digitally, at any time.

Actor Colm Feore walking down street
Harry Rosen Role Model Colm Feore (Photo: Harry Rosen)

Can you describe an instance of out-of-the-box thinking that Harry Rosen has spearheaded? 

As so many of our competitors have abandoned the store, we dug our heels in. We said this really doesn’t have to be a battle between our store business and online business, but rather the two can work with one another. In fact, they need to. We’ve invested in training for our people on how to engage clients with the same professionalism over text as they would in person. One of the boldest decisions we made was not to work with an out-of-the-box software partner for this, but rather to custom-build an application that met the unique needs of our clothing advisors. Our over-90 percent participation rate across our stores is proof we made the right call. 

What does the future of shopping and retail look like for you? 

As the son and grandson of merchants, I have to start with the fact that nothing works if you don’t have a great product. We haven’t lost sight of that in 67 years and we couldn’t build loyalty without it. When it comes to the future of retail and shopping experiences, I believe it all centres around two main ideas: i) reward your clients with a better experience each and every time they engage with you, and ii) put the client in complete control of how they shop. Consumers are more savvy than ever, and they are always asking themselves if they are getting as much back from a company as they are putting in. This can be rewarding a client with a special deal or giving them first-access to meaningful experiences.

It also means making shopping faster and more streamlined by knowing their sizing or preferences. We strive to show our clients that every time they shop with us will make the next time more personalized, whether it’s online or in-store. We also know that the digital world is setting the clients’ expectations and we need to meet them. Our client can cancel a reservation easily on their Open Table app if something pops up, so we need to ensure they can easily reschedule their appointment with a few taps or with a quick text. We know that clients want packages to arrive quickly—so we need to pick, pack, and ship just as fast as Amazon. These two trends are going to ultimately determine who succeeds and who fails in retail.


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