The technology wasn't the hurdle though. People knew it was perfectly feasible. In fact online shopping pre-dates the web and mainstream adoption of the internet by more than a decade. It was customers feeling safe enough entering bank details online and the whole thing being sufficiently secure. Which isn't an irrational thing to worry about.

Sears flubbed the transition to online catalog shopping in such a spectacular manner that it really was the complete (im)perfect storm for them. In the late 1980's Sears already had their fingers in so many related pies that they could have easily tolerated falling flat on their faces in at least one of the required aspects and still probably succeeded, but instead they whiffed every single one of them.

Remember Prodigy Online? The early online platform that fought for dominance in the dawn of the dial-up era along with the likes of AOL and Compuserve? It was started as a joint venture between IBM and Sears. The Discover credit card? Launched by Sears. Catalog shopping with a nationwide logistics network? You guessed it, already famously pioneered by Sears.

All they had to do was put these things together: Put the Sears catalog, already a household name at that point, on the computer. Accept credit cards over the network. Ship the stuff to people's homes easily, cheaply, conveniently. They could have made themselves the undisputed king of general merchandise online shopping before anyone else even had a hope of gaining a foothold in that arena via an established catalog and logistics operation. And they didn't.

But I think the real problem Sears had was refusing even after the writing was already on the wall to let go of the brick-and-mortar-first retail model, including allowing their in store selection and pricing to comprise the entirety of their online catalog for way too long, which enabled other online retailers to either offer a wider selection of stuff to buy or the same stuff at a lower price. Or both.

This is especially ironic considering that the Sears and Roebuck was a century old meme that was synonymous with being able to order any damn fool ridiculous thing and have it shipped to your homestead. You want a house? A snowblower? A pocketwatch? A case of light bulbs? A shotgun? Order it from Sears! But Sears steadfastly spent the early 2000's hawking basically only their in store selection -- apparently consisting largely of Eddie Bauer sweaters and out of date consumer electronics by that time -- at full in-store MSRP on their web site. Thereupon Amazon, Wal Mart, Best Buy, and to some extent Target stepped in and ate their lunch.

And Sears didn't allow third party sellers to participate on their web site (and thus expand their merchandise selection) until 2010. Amazon, meanwhile, had already been doing it for a decade at that point.

There were other systemic issues behind the scenes in Sears management brewing even before then. But cratering so hard right at the start line of the online shopping era certainly didn't help. By the time even the random man on the street could see that Sears was now fucked, it would have taken way more money than they actually had to turn the ship around.