Boomers still swear by 10 high-street staples you skip, from Macy’s to Sears and Kay Jewelers

Two generations walk the same aisles yet see different worlds. One chases routine and touch; the other chases speed and meaning.

That gap shows up most clearly in where people choose to spend a Saturday. For many over-60s, a familiar store still feels like a promise. For under-25s, it often looks like a queue and a fluorescent headache. The clash runs deeper than taste. It reflects how values, tech and time pressure shape every purchase.

What the split says about shopping now

Baby boomers prize the ritual. They value service, a tidy return desk and the comfort of a store account. They enjoy aisles, fitting rooms and chatty staff. Gen Z buys by vibe and values. They want brands that speak in a voice they recognise and that back causes they believe in. They want speed, clarity and a tight edit. They check reviews, filter by ethics and tap to pay.

For Gen Z, efficiency feels like luxury. For boomers, being known by name still feels like care.

That difference makes certain chains a magnet for one group and a dead zone for the other. Here are the flashpoints—plus what they reveal about where high-street retail heads next.

The ten stores causing the biggest divide

Macy’s and JCPenney: perfume counters to packed rails

Department stores once marked a day out. People dressed up, walked through perfume mists and hunted for a blue-ticket bargain. Service desks handled problems with a smile. Store cards gave a reason to return. Today, younger shoppers call the format noisy. They want a brand edit, not a forest of rails. They value direct-to-consumer clarity, clean layouts and faster checkout.

Younger shoppers say “less but better” beats “everything under one roof”.

Sears: catalogue dreams to quiet corridors

For many families, Sears meant first appliances, first tools and a first credit line. The catalogue sat by the phone. That memory still holds power for older shoppers. For Gen Z, the store reads as a throwback. Lighting feels tired, signage looks dated and the brand promise sounds faint. They buy a washer with two clicks or pick a laptop from a sleek tech brand with same-day collection.

Kay, Zales and the new meaning of romance

Ritual drives jewellery for older couples. They want to see a stone sparkle under the shop lights and ask about repairs. Gen Z sees romance in different places. They choose lab-grown diamonds for ethics and price. They commission a small designer or choose vintage. Authenticity beats prestige. A glassy mall shopfront can feel like an upsell, not a moment.

Payless and the rise of the sneaker identity

Value chains kitted out whole families at once. That made sense when shoes served function first. Today, trainers tell a story. Colourways, drops and collabs carry status. Younger buyers want sustainable materials or a design with cultural roots. A wall of lookalikes sends them straight to a resale app.

Pier 1 and Bed Bath & Beyond: clutter versus calm

Pier 1 sold a packaged version of global taste. Mosaic lamps, bamboo chairs and patterned throws gave suburban rooms a burst of elsewhere. Gen Z prefers the real thing or a rescue. They hunt for second-hand and fix up furniture. They use peer-to-peer platforms and local makers. Bed Bath & Beyond triggers the same reaction. Aisles feel long. Choices feel endless. Younger shoppers pick a narrow range from a brand that matches their palette, read reviews and tap buy.

Choice used to impress; curation now converts.

Dillard’s, Talbots and the comfort of proper

For many boomers, a suit that fits and a dress that covers the occasion still matters. Dillard’s and Talbots deliver that safe option. Clean lines, sensible cuts and a neat till. Gen Z dresses for expression and ease. They want stretch, play and mix-and-match. They also want sizing that moves beyond binary rails. A shop that signals “correct” can feel like a quiet no.

Hobby Lobby and the move from aisles to apps

Crafters love a long browse, a glue-gun find and a half-price wreath. That mood fills a trolley and a Sunday afternoon. Younger makers run workshops on screens, buy from small artists, and use digital tools to design. Many skip the chain for values reasons. Creativity still thrives; it just lives on a different shelf.

Staples and the clean-screen office

Fresh stationery still thrills. A new pen can spark a plan. Boomers see order in a label maker and a filing cabinet. Gen Z manages notes, calendars and storage online. A tidy desktop lives in the cloud. Printer paper feels like clutter, not progress.

What drives the split

• Time: younger buyers optimise for speed, older buyers make time for the trip.
• Identity: Gen Z picks brands that mirror beliefs; boomers pick stores that mirror routine.
• Design: minimal edits and clear signage beat deep aisles and mixed racks.
• Ethics: sustainability, supply chain and lab-grown options guide younger wallets.
• Community: peer reviews and creators replace sales assistants as trusted guides.
• Value: coupons and loyalty cards speak to boomers; transparent pricing and free returns win Gen Z.

Who wins at the till

Stores that bridge the gap keep both camps. Department chains can shrink floor space, spotlight fewer brands and add strong click-and-collect. Jewellery shops can stock lab-grown and custom design while keeping repair benches. Home chains can pair in-store demos with rapid delivery and no-fuss returns. Office stores can lean into services—tech support, on-demand printing, parcel points—and curate premium stationery rather than piles of paper.

Retail that respects attention—less friction, more purpose—pulls crowds across generations.

Practical takeaways for shoppers

If you love the ritual, use it. Ask sales staff for price matches and alterations. Put coupons in a wallet app. For fast shoppers, build a shortlist before you go. Set alerts for restocks. Use store pickup to test fit without wandering. For gifts, split the difference: order ethical pieces from small makers and collect them from a local pop-up.

What this means for the next 12 months

Expect more hybrid formats: smaller city branches, shop-in-shop corners and returns desks that double as service bars. Look for resale racks inside mid-market fashion, crafting events hosted by independent artists, and jewellery counters that show carbon data next to carat data. Stationery chains will likely add co-working pods and device trade-ins to justify the trip. The winners will edit bravely and talk plainly about values.

A quick way to test your own habits

Pick one of the ten chains. Set a 20-minute timer. Can you find the item, compare three options and pay within that window? If not, try the same mission with a direct-to-consumer brand or a curated boutique. The route that saves you time, stress and returns shows which side of the aisle you stand on—no judgment, just data you can use next weekend.