NEW YORK —  If you’re staying at a hotel and realize you didn’t quite pack right for your trip, apparel retailer Gap wants to come to your rescue.

At Virgin Hotels, guests can now open up the hotel’s app, Lucy, and reserve items for purchase from Gap. The idea is that customers might want to buy a jacket if the weather is unexpectedly cold, or maybe some workout gear if they realize they have some free time for a jog. The hotel concierge then picks up the order at a local Gap store, stows it in the guest’s closet and puts the purchase on their hotel tab.

“The ability to share each other’s customers, that acquisition is of high value,” said Tricia Nichols, Gap’s global lead of consumer engagement and partnerships, in a presentation at the National Retail Federation’s Big Show.

It’s an experimental way for Gap to sell clothes, and it shows how far retailers are venturing out of their comfort zones as they aim to stay relevant in a challenging moment: Consumers are spending more time on their gadgets, and on-demand delivery and transportation apps are conditioning them to expect greater speed and convenience.

The NRF’s expo and convention, which has drawn thousands of retail industry professionals to New York this week, has been heavy on demonstrations and discussions of similarly-minded attempts to drum up bigger sales by catering to newly-emerging shopping preferences or with new technologies.

Snacking giant Hershey, for example, said Sunday that it has tested an in-store display that incorporates facial emotion recognition technology. When shoppers smile, they’re dispensed a free piece of chocolate.  (And sorry, chocolate lovers, the technology is able to recognize when you try to come back for seconds.)

Hershey is also testing ways it might use technology to personalize its treats, since shoppers increasingly seem interested in products that are one-of-a-kind.  They’ve implemented 3D printing of chocolate in Hershey Chocolate World store, where shoppers can watch their snack get made.  And in some Giant Eagle grocery stores, they’ve rolled out machines that allow shoppers to personalize the packaging of an oversized Hershey Kiss. This effort has already had a dollars-and-cents impact, doubling sales of associated Kisses products in stores where it has been launched.

“This is a way to really capture and transition from impulse purchase to more of a planned purchase,” said Michele Buck, president for North America at Hershey, in a convention presentation.

Like Hershey, plenty of other brands were showing off technology that they hope can turn shopping into memorable experience instead of a mundane errand. At Intel’s booth in the sprawling Javits Center expo hall, demonstrators showed how its RealSense 3D cameras were being used in tests in some Nordstrom stores to measure shoppers’ shoe size. The cameras are embedded in a platform that the shopper stands on, and within about three seconds, scan their feet. Shoppers then get detailed information on not only what size they should wear, but on slight differences in, say, the width of their left and right foot. The idea is that this should help the store employee guide the shopper to a pair of shoes that is especially well-suited for their body.

Wander the long aisles of booths at the expo, and you’ll also see plenty of attempts to improve the online shopping experience. Outdoor apparel seller North Face is turning to software that’s designed to mimic online the experience of having a real-life personal shopper. Customers can answer a series of questions in a conversational way, such as mentioning that they’re “looking for something that will be good to wear in Jackson Hole in February.” Technology that relies on IBM Watson will help figure out what item that shopper should buy. Watson’s natural-language processing ability will process the shopper’s request, and the system will analyze the likely precipitation, wind and temperature conditions in that location, among other things, to hopefully recommend the right jacket.
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