I remember when my local paper added a "technology" column (mid-'80s) and some of the articles that it featured as the internet took shape. Seems like there were articles about the early web browsers, the increasing popularity of the "World Wide Web", and discussion of the first online purchases all within a year or so (1993-94?)
One key point - repeated in several articles by the tech columnist - was the answer to the question: "Who shops online?" At that time, the internet was seen as the domain of younger, single men. More than that, there seemed to be bit of mockery present... Star Trek fandom references, comments about the back offices of the university Computer Science lab, and so on. I recall reading a few testy letters to the editor that were reactions to that stuff.
I guess Sears, if they studied the potential at all, concluded that online activity was a niche market that they could safely ignore. Oops.
Easy to judge in hindsight, but I remember I was looking for a Craftsman tool back in the 90s.
What stuck with me was that the local store didn’t have it and when I went online, I realized that that the web site was worse than useless for either finding inventory in other stores or even basic information on store hours.
About that same time, I stopped being a loyal Sears customer and began looking elsewhere.