You have tremendous potential, given your candor and open-mindedness.
One thing to think about is that we are often unwittingly attracted to the most novel or conceptually interesting clothing even if it is objectively the more loud and unflattering choice. Try to think of the clothes as tools and constituent parts in a greater armature, not as individual pieces of flair. This way you won't have particular attachment to an individual item but treat them as modular components in a whole.
Put down the Thesaurus, @sprout2
You got mad potential bro, your head is in the game. But you gotta check yaself before you wreck yaself.
Check this: sometimes we grab the more dope choice cuz it looks straight fire but it's TOO hot, looks too blinged out nawmean? You gotta go for that lowkey swag, build each piece up till you got a HALO around you, for real for real.