Grayson, do not even think about gear/clothing except for safety. Where I live (Manhattan) most bikers I see are not riding for sport. They are commuting or working as delivery/messenger bikers. Virtually NONE of them wear "proper" stuff. It just ISN"T done.
The spandex getup for biking elicits howls of laughter from LOTS of people. Honestly, I would shave my head before I would walk through my apartment building lobby in full Biking Regalia.
Being seriously cool on a bike means cutting one pants leg off with scissors (and you don't hem it -- gotta be ragged). Alternatively, you narrow your pants leg with a big safety pin. To carry stuff on a bike, you can strap one a milk crate or a large plastic bucket.
It is NOT "crazy" to wear sweats and Cuddl Duds. I LOVE Cuddl Duds. Cotton isn't practical for wicking, but otherwise, it's fine.
People get "into" gear for all kinds of reasons. Some of it is practical, some simply fun, some is silly snobbery. Over time, you will decide what YOU need, and you will acquire it. In the meantime, stick to your very admirable goals and have fun.
Pam



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