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"how hard is it (not a rhetorical question) to be happy and joyous while dressed dourly?"

There need not be any connection whatsoever, additionally, the relationship may be inverse as well to some in some contexts, and one can also change clothing according to the occasion; festive, sporty, tactical, scary, solemn, naked, etc. Just like songs change, for celebrating, for mourning, for battle, for relaxation. In this way, and many others, anarchists are unremarkable people. People are more alike than dissimilar.

"is the point that happiness is too associated with conformity?"

It need not be, but a range between bland contentedness and mellow melancholy seems to be. Assertion. ONLY ECSTASY AND EYE RIPPING ANGUISH ARE ALLOWED. MANICURE YOUR AFFECTS, ANARCHISTS! HAVE BEAUTIFUL FEELINGS AS WELL AS IDEAS AND ASPECT! VIRTUE!!!!!! Not saying this is what you claim, this is just a histrionic farcical tangent.

"does that change as an anarchist marker as other people acknowledge/become more unhappy?"

Do you mean that an anarchist should be bright and colorful in order to contrast a gloomy and dismal world?
That the aesthetic intention is to be against the grain, shifting in opposition to the norms and trends?
Is this in conflict with the desire to wear and look like you want without regard for how you're perceived?

I would further inconvenience the whole question by asking questions pointing to annoying paths: can an anarchist even be beautiful? is anarchy by definition ugly? isn't it that the world is really bright and beautiful and anarchists are the ugly rejects?
Again reminded of the Crimethinc medusa poster, like the last time a similar topic was circulated.

At some point, after getting dizzy in the carousel of words, we can recognize that we're dumb animals that say "ooh, shiny thing!" and other things that hint things to us related to our very mundane and absurd biological impulses, not lofty ideals or musings. People are not the only animal that ornaments (their surrounding and their personal appearance), or marvels at beauty. I've even seen stray dogs gather on the top of a hill to watch the sunset, moved by its beauty. And stray dogs, even when in a particularly blatant case of pack hierarchy, are more anarchist than people, including anarchist people.

What are doggy aesthetics?