I'd like to conceal my identity as much as possible while shopping online. I try not to resort to online transactions in my daily consumer habits, in part because of privacy, but also because cash is just generally better for budgeting. I'm not Opsec paranoid about having my identity found out, but I don't want to make it easy for retailers to create a consumer profile about me.
I've toyed with the idea of prepaid cards and gift cards. Paying in cash for digital credit at a brick and mortar won't stop the FBI from coming after you, but it does address the inherent problem of disclosing your credit card online. The former is expensive, inefficient, and often times has high fees and all sorts of gotchas they don't disclose when purchasing the card. The latter is better but also a walled garden.
Then there's the fundamental issue of where to ship your merchandise, if you're buying physical commodity. I PO box seems like a good idea initially, but, even with an alias (which, I think, might be illegal to do), you're still associating yourself with one or two recipient accounts--not only that, but you're associating yourself with a static recipient even if you move, so it can even be detrimental. You can persuade someone, such as a neighbor, to be a proxy for your stuff, but that has to be a relationship with a lot of trust, not to mention patience for our obsessive insanity. You could accept their packages while they accept your packages in a kind of pseudo-onion routing way of concealing your actual buying habits, but that seems unrealistic.
Is it hopeless? Does anyone else have this concern, or am I just unhealthily concerned with this topic to detract from other anxieties in my life I have less perceived control over? If there are people like me out there, maybe we can put our heads together and figure something out.