I’ve seen this scenario before, but I will not name names. A woman with a delightful and sensible figure, who looks quite gorgeous from any angle, cranes her neck around to the mirror and asks, to nobody in particular, “Does this make my ass look big?”

You look around. Actually, she is asking you. There really is only one reasonable answer to that question—but it isn’t the truth.
Alas, here is the problem with shopping. It’s uniquely personal, yet the massive mainstream retailers have to be totally impersonal and personal at the same time. So what you often get is messaging—advertising that convinces you of what is actually untrue, and jeans or outfits that really don’t quite fit. The brand slogan and the ad campaign are supposed to convince you that you are in love with something that you’re not. But, lacking other options, you settle.

That may be changing, in two very distinct ways.

Tech-Enabled Customization

This is the video that Ali Fenn, head of marketing for the custom-jeans outfit INDi, sent me after our conversation about customized shopping and fitting experiences for women in the jeans category.

Fenn says the real opportunity for retailers is making jeans for women that fit on real bodies, and to deliver that category in a way that is not manipulative.

Retailers currently depend on fit models—perfectly proportioned women between sizes 2 and 6—who are supposed to represent everywoman (even though the average size woman in the U.S. wears a size 14) to get an idea of how clothes will fit and drape on real bodies.

“Jeans shopping is tough; 70% of women and 40% of men say they wish they had jeans that fit,” says Fenn. “It’s also emotional for people. People have their own body issues. There’s something about being able to go through this process online in a way that you wouldn’t go through in a brick-and-mortar.”

The INDi Process, as they call it, helps customers use technology and e-commerce to find jeans that fit them. The video explains it pretty well.

Are retailers like Saks, Macy’s, or even K-Mart in trouble? Will they be able to offer this same customization?

Fenn isn’t critical of the big shops, but she says that the opportunity exists to change the current model, if people can grow comfortable with scanning technology and what’s new.

The evolution would be, eventually, a highly personal fitting room in your own apartment, set up with basic software and a Kinect by Microsoft, for example.

“The friction is that it’s new,” says Finn. “There’s a slight hesitation about not knowing exactly what it’s looking like.”

Still, Finn expects the future of offline shopping experiences to look like a mix of the highly customized version one can get using e-commerce at home or on a mobile device, with the convenience and reach of bricks-and-mortar. She even thinks there will be pairings of couture online-only brands that will do pop-up stores within the major chains, like Macy’s.

“Ultimately, they need to merge,” says Fenn. “On the one hand, going and trying on a bunch of clothes with friends…is a good thing. On the other hand, you don’t find something that fits great, or you are 20 pounds heavier than someone else, it can be not so fun.”

“You can do it online, but it can be tailored to you,” she says.

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