The grand department stores of yesterday were monuments to retail ambition—soaring atriums, ornate facades, and carefully curated floor plans that guided customers through a journey of discovery. Macy’s Herald Square, with its wooden escalators and iconic window displays, embodied this vision. But in the digital age, those same architectural principles that once drew millions have become liabilities. The walls that created destination shopping experiences now create friction in the user experience. To reclaim its position as America’s department store, Macy’s must tear down its digital walls—not to abandon its heritage, but to rebuild with the wisdom gained from watching competitors stumble.
The Department Store Mentality in Digital Spaces
Walk into a physical Macy’s and the layout makes sense. Cosmetics near the entrance, men’s wear on one floor, home goods on another. This deliberate separation created opportunities for serendipitous discovery and maximized real estate value. But Macy’s translated this same structure directly into its digital experience, creating a website that feels like navigating a multi-story building rather than shopping online.
Amazon learned early that digital retail follows different physics. There are no floors to climb, no departments to traverse. Every product should feel equally accessible, with the algorithm deciding what to surface rather than the floor plan. Walmart initially made the opposite mistake, their early ecommerce efforts replicated the big-box warehouse experience online, overwhelming users with too many options and insufficient curation. Target, meanwhile, struggled to bridge their “cheap chic” in-store experience with a digital presence that felt neither particularly affordable nor especially stylish.
Macy’s can learn from all three failures. The key is recognizing that digital walls are made of navigation menus, category hierarchies, and siloed shopping experiences, and they’re just as restrictive as physical ones.
Removing the Checkout Counter
Perhaps the most literal wall in retail is the checkout counter, the final barrier between desire and ownership. In physical stores, this makes sense. Online, it’s an artifact that creates unnecessary friction.
Amazon’s one-click purchasing demolished this wall entirely. The company recognized that every additional step in checkout represents an opportunity for the customer to reconsider, to comparison shop, or simply to abandon their cart. Yet Macy’s checkout process remains a multi-page odyssey requiring account creation, address confirmation, shipping method selection, payment entry, and order review.
Walmart’s early attempts at streamlined checkout created problems of their own. By reducing friction without building trust, they saw increased fraud and returns. Their solution, adding back verification steps, moved in the wrong direction. Target found a middle ground but struggled with the technical implementation, leading to checkout errors that frustrated users at the worst possible moment.
The solution isn’t simply copying Amazon’s one-click patent (which expired in 2017) but understanding the underlying principle: save everything that can be saved, default everything that can be defaulted, and reduce decisions to the absolute minimum. Macy’s should know my size, address, preferred payment method, and typical shipping choice before I ever add an item to my cart. The checkout process should feel like confirmation, not interrogation.
The Paradox of Choice and the Power of Curation
Department stores built their reputation on selection. Why buy a shirt at a specialty store when Macy’s stocks two hundred options? This abundance was a feature in physical retail, where browsing was part of the experience. Online, it becomes paralyzed.
Walmart fell into this trap spectacularly when it opened its marketplace to third-party sellers. Searching for “men’s dress shirt” might return thousands of results, many of dubious quality, with no clear way to distinguish between Walmart’s curated inventory and marketplace randomness. The user experience became chaotic, undermining the trust customers had in the Walmart brand.
Amazon solved this through obsessive categorization, filtering, and algorithmic ranking. But even Amazon users report frustration with the sheer volume of choice, particularly as counterfeit goods and review manipulation have eroded trust in their curation.
Target took a different approach, leaning heavily into private-label brands and designer collaborations. Their digital experience emphasizes curation over comprehensiveness. This works for Target’s younger, design-conscious customer base but sacrifices the “find everything” value proposition that defined department stores.
Macy’s occupies a unique middle ground. The solution lies in progressive disclosure, presenting a curated selection initially, with the full catalog available to those who want to dig deeper. Start each category with twenty staff picks, algorithmically personalized. If customers want more, they can expand filters. If they want everything, they can request the full inventory. This respects both the casual browser and the determined searcher without overwhelming either.
Demolishing the Walls Between Channels
The most insidious walls in modern retail are invisible, the artificial boundaries between online, mobile, and in-store experiences. A customer might browse on their phone during their commute, research on their laptop at work, and purchase in-store on the weekend. Macy’s treats each of these as separate transactions.
Walmart’s acquisition of Jet.com was supposed to solve this problem by importing digital-native expertise. Instead, it highlighted how deeply siloed their operations were. In-store inventory systems didn’t communicate with online availability. Returns purchased online but returned in-store became data black holes. Pickup orders existed in limbo between the digital and physical worlds.
Amazon built its business without these legacy systems, giving it an architectural advantage. But even they struggled when entering physical retail with Amazon Go and Whole Foods. The challenge isn’t technical, it’s organizational. Different divisions with different metrics, incentive structures, and customer databases.
Target made the most progress here with its store-as-fulfillment-center model. By recognizing that their physical locations were assets, not liabilities, they turned stores into micro-distribution centers. This reduced shipping times and costs while increasing in-store traffic as customers picked up orders.
Macy’s has over 500 locations that could serve this dual purpose, but the walls between divisions prevent it. The UX solution requires organizational restructuring. Every product page should show real-time in-store availability at nearby locations. Every cart should offer same-day pickup as the default shipping method where possible. Every loyalty point, every saved item, every size preference should follow the customer across channels seamlessly.
The Search Problem Nobody Solved
Type “red dress” into any major retailer’s search bar and you’ll see the problem immediately. Results include burgundy, crimson, scarlet, rust, and pink items that someone tagged as red. You’ll see red accessories paired with non-red dresses. You’ll see dresses that are partially red. The search function, the most direct route to purchase, is a maze of irrelevance.
Amazon’s solution has been machine learning trained on billions of searches and purchases. It’s effective but opaque. Users can’t understand why certain results appear or how to refine them. Walmart’s search feels powered solely by keywords, returning literal matches without understanding intent. Target’s search works reasonably well for their core categories, but falls apart for anything outside their typical inventory.
The underlying issue is that traditional search works well for known-item searching (I want “Nike Air Max 90 size 10”) but fails for exploratory searching (I need “something to wear to a summer wedding”). Department store shopping was always about the latter; customers came in with vague needs and left with specific solutions.
Macy’s should implement conversational search that asks clarifying questions. Not in an annoying chatbot way, but through progressive filtering that feels natural. “Red dress” could trigger: “What’s the occasion?” with options for casual, work, cocktail, formal. “Any particular style?” with visual examples rather than fashion jargon. This transforms search from keyword matching into guided discovery.
The Ghost Town Problem of Abandoned Features
Every major retailer has built features that users ignore. Walmart has a sophisticated list-making system that nobody uses. Target’s registry function works well, but exists in isolation from the rest of the shopping experience. Amazon’s “Inspire” shopping feed feels like a desperate attempt to become TikTok.
These abandoned features create what UX designers call “ghost town” experiences, empty spaces that remind users the platform isn’t as active as it pretends to be. They also clutter interfaces with entry points nobody clicks.
Macy’s digital properties are significantly affected by this. The mobile app includes a “scan to shop” feature that requires users to photograph items in-store to get information already available on tags. There’s a “trending” section that appears manually curated and rarely updated. Social sharing options sit prominently despite minimal usage.
The solution isn’t adding more features but auditing existing ones ruthlessly. Every interface element should either be frequently used or quietly removed. This requires instrumentation—tracking not just clicks but also hover states, scroll depth, and time spent. Features used by less than 5% of users should be reconsidered. Features used by less than 1% should be removed unless they serve a specific strategic purpose.
Personalization Without Creepiness
Amazon’s recommendation engine is legendary. “Customers who bought this also bought…” drives a significant percentage of purchases. But Amazon’s approach can feel invasive. Search for something once and you’ll see ads for it everywhere for weeks.
Walmart tried to replicate this system but with insufficient data, the recommendations felt random. “Because you bought cereal, you might like automotive oil.” Target famously predicted a teenager’s pregnancy before her father knew, highlighting the ethical concerns of over-aggressive personalization.
The wall to tear down here is the false choice between generic experiences and invasive tracking. Macy’s should implement transparent personalization where users understand and control how their data is used. This means explicit opt-ins for tracking, clear explanations of why recommendations appear, and easy ways to reset or refine preferences.
More importantly, personalization should feel helpful rather than surveillant. Instead of “we noticed you looked at this product,” try “this might work with the dress you bought last week.” Focus on completing outfits, coordinating home decor, and suggesting complementary items rather than showing users the same thing repeatedly.
Mobile-First Without Mobile-Only Thinking
Over 60% of Macy’s traffic comes from mobile devices, yet the mobile experience feels like a compressed version of the desktop site rather than a designed-for-mobile experience. This is the same mistake Walmart made initially, assuming mobile was just smaller desktop.
Amazon’s mobile app prioritizes speed and simplicity. Product pages load quickly with essential information above the fold. The search bar is always accessible. One-tap reordering of frequently purchased items reduces friction. But the Amazon app sacrifices discoverability; it’s harder to browse casually.
Target’s mobile app excels at specific tasks (finding items in-store, checking prices) but struggles as a general shopping tool. The navigation feels cramped and the imagery-heavy approach that works on desktop becomes overwhelming on small screens.
Macy’s needs to recognize that mobile shoppers have different intents than desktop users. Mobile sessions are often quick, task-oriented, and context-dependent. Someone in a store is checking prices. Someone on a bus is browsing aspirationally. Someone in bed late-night shopping.
The UX should adapt to these contexts. Quick access to scannable deals and recently viewed items. Generous touch targets and minimal text entry. Vertical scrolling as the primary navigation pattern rather than nested menus. And critically, progressive web app functionality that works offline and loads near-instantly.
The Returns Experience as Competitive Advantage
Returns are where e-commerce user experiences go to die. After the purchase high comes the return low, hunting for order numbers, printing labels, finding boxes, driving to shipping locations. It’s friction designed to discourage returns, but it only discourages repeat purchases.
Amazon made returns easy through Kohl’s drop-off locations and QR code labels that require no printer. But this was born of necessity—their massive scale meant return friction was costing them customers. Walmart’s return process remains clunky, requiring specific documentation and often offering only store credit rather than refunds. Target’s return experience is better in-store than online, creating a disconnect.
Macy’s has a unique advantage here, extensive physical locations that could accept returns instantly. But the current process doesn’t capitalize on this. Customers who bought online must bring receipts, often wait for verification, and deal with separate customer service lines.
The ideal experience: open the app, select the item to return, generate a QR code, walk into any Macy’s, scan at a dedicated kiosk, drop the item, done. Refund processes immediately. No boxes, no labels, no questions. This transforms returns from a penalty into a convenience, reducing the psychological barrier to online purchasing.
Loyalty Programs That Feel Like Rewards, Not Homework
Macy’s Star Rewards program epitomizes the department store approach to loyalty, tiered status levels, points that expire, rewards that require activation, and complex redemption rules. It’s loyalty as an obligation rather than appreciation.
Amazon Prime isn’t a loyalty program in the traditional sense, it’s a subscription that delivers concrete benefits immediately. No points to track, no status to maintain, just pay annually and get free shipping. Walmart tried to replicate this with Walmart+ but struggled to communicate value beyond shipping. Target’s Circle program improves on points-based systems by offering automatic discounts rather than requiring redemption.
The wall to demolish is the artificial complexity that makes loyalty programs feel like second jobs. Macy’s should automatically apply the best available discount at checkout. No codes to enter, no points to redeem manually, no tracking required. Show customers how much they’ve saved over time to build appreciation, but remove the cognitive load of optimization.
Additionally, loyalty should unlock experiences, not just discounts. Early access to sales, exclusive products, or personalized styling sessions for top-tier members. Make status feel like VIP treatment rather than coupon clipping.
The Content Problem
Amazon famously has minimal editorial content, their pages are functional, data-driven, focused on conversion. Walmart’s attempts at content marketing feel disjointed from the shopping experience. Target’s content works better, particularly around home decor and style, but it exists separately from commerce.
Macy’s has a heritage of editorial curation, window displays, catalog spreads, fashion shows. This should be a digital differentiator, not an abandoned strength. The wall to tear down is the separation between content and commerce.
Every style guide, trend report, or outfit inspiration should have embedded shopping functionality. Not affiliate links or separate product pages, but seamless integration where clicking an item in an editorial image adds it to your cart. This was Macy’s physical advantage, seeing complete room displays and full outfits, and it can work digitally.
Critically, this content should feel aspirational but accessible. Show outfits at different price points. Suggest alternatives for sold-out items. Make it easy to shop the full look or individual pieces. Transform browsing from a random walk through categories into a guided exploration.
Speed as a Foundation, Not a Feature
Every major retailer talks about site speed, but few treat it as foundational. Amazon obsesses over milliseconds, knowing that every 100ms of latency costs them revenue. Walmart improved their speed significantly in recent years but still suffers from slow load times on product-heavy pages. Target’s site is reasonably fast but their app can lag during high-traffic periods.
Macy’s digital properties are notoriously slow, pages that take seconds to load, images that pop in gradually, interactions that feel delayed. This isn’t just an inconvenience; it’s a wall between intent and action.
The UX solution requires technical investment but also design discipline. Lazy loading for below-the-fold content. Aggressive image optimization. Minimal third-party scripts. Edge caching for common interactions. Progressive enhancement that shows core content immediately and adds enhancements as they load.
Users perceive speed not just through objective load times but through perceived performance. Skeleton screens that show content structure while loading. Optimistic UI updates that assume actions succeeded rather than waiting for confirmation. Preloading likely next steps in the user journey.
The Vision: A Department Store That Exists Everywhere and Nowhere
The ultimate goal isn’t to replicate Amazon, Walmart, or Target. It’s to reimagine what a department store means in the digital age. Physical department stores succeeded because they aggregated selection, provided curation, offered service, and created experiences worth traveling for. Digital Macy’s should do the same, without the constraints of physical space.
This means tearing down the artificial walls between categories, channels, and experiences. It means removing friction at every step while adding delight where it matters. It means treating personalization as service rather than surveillance. It means making the complex feel simple and the overwhelming feel manageable.
The companies Macy’s should learn from made mistakes because they were pioneers. Amazon built systems that work at their scale but feel impersonal. Walmart struggled to translate physical retail dominance online. Target found success by not trying to be everything to everyone. Macy’s can learn from each of these—the efficiency, the reach, the curation, while maintaining what made department stores special: the feeling that everything you need is here, and someone who cares is helping you find it.
The walls come down not to abandon structure but to rebuild with intention. Every element should serve the customer’s journey, not the company’s organizational chart. The result won’t look like the competition because it shouldn’t. It should look like Macy’s understood what made them America’s department store and rebuilt that magic for the world that exists today.