The Fedora Meme is a projective and transformative criticism. Fedora's were/are popularly associated with style and a sense of composure. Contemporarily, some portions within the internet project the fedora wearer as a signifier for social ineptness.
Its association with ancaps are a by-product of both psyops and opposing ideological critiques. I say, 'psyop', because it is obvious that all anarchist groups are extensively catalogued by intelligence agencies, and it is established that there exists multiple programs to ensure a splintered audience of persons who are opposed to centralized systems.
On the other hand, it is precisely a (neo-?)modern critique upon a person of "formal" attire. Historically, fedoras have seen their usages as meaningful expressions of empowerment, sophistication, style, danger and power. That there exists a consistent mnemonic dialogue against certain proponents of X positions suggests that the "fedora" is undergoing a forced projection that restates an extremely personal dislike of a person's stance and the implied meaning of said person's awkwardness.
The meme attempts to materialize itself by its widespread utility but its critique is ultimately a superficial one. Broken down, the meme greatly suffers, particularly because it's an exacting sign of social conformity that projects a relative sense of displeasure.