Men’s Wearhouse is a U.S menswear retailer with over 600 stores, known for affordable, quality formalwear and a customer-first approach, encapsulated by its motto: “You’re going to like the way you look. I guarantee it.”
Looking to modernize its checkout experience and connect with a new generation of shoppers, we set out to reimagine the last stage of the user’s purchasing cycle “from cart to completed order”.
With users so close to completing their purchase, it is almost unbearable to think about them leaving their cart because of an unnecessary barrier to checkout.
Over the course of an eight-week collaborative sprint, we immersed ourselves in the world of retail checkout flows, generational buying behaviors, and modern expectations around trust. Our goal was clear: transform the checkout from a transactional step into a meaningful touchpoint for driving conversion, building trust, and fostering loyalty.
Discovery
Research
Define
What became immediately clear was this:
Despite our efforts to optimize, our checkout experience is creating friction at critical moments, causing users to slow down, hesitate, or drop off entirely.
Pattern #1
Checkout Flow Is Cluttered With Unnecessary Friction
From our Medallia data, customers feedback highlighted login issues, failed password resets,
The heuristic evaluation confirmed these barriers, checkout includes a prompt asking users to choose between signing in or continuing as guest, adding an extra step.
In contrast, competitors streamline this flow by defaulting to guest checkout or surfacing express payment options right away.
Pattern #2
Lack of Clarity Undermines Trust
From our Medallia data, customer feedback highlighted confusion around shipping costs, promo codes, and return policies.
The heuristic evaluation confirmed these gaps form fields lacked clarity, inline error messaging was missing, and there was no visibility into shipping cutoff times.
In contrast, competitors made this information clear by displaying return policies upfront, showing free shipping thresholds in real time, and even allowing loyalty signups directly within the checkout flow.
Pattern #3
Value Systems Feel Disconnected
From our Medallia data, loyalty members struggled to redeem certificates or didn’t see their rewards reflected during checkout.
The heuristic evaluation revealed that loyalty codes had to be entered manually, with no prompts or visibility into available rewards.
By comparison, our competitors integrated loyalty more seamlessly, auto-recognizing returning users, surfacing rewards in context, and even allowing new members to enroll directly within the checkout flow.
Final Design
For a detailed, step by step walkthrough of the full flow I’d be happy to share more. Let's connect!
