My limited understanding is to get the following right in the following order,
Break them at your peril (insofar you don't know) or to send "it takes one to know one"/non-literal IDGAF messages (insofar you do know)...
Their situation (mandatory suits at white collar interviews, etc. )
Your style (certain clothes project certain styles, e.g. goth dresses goth, nerd dresses nerd, classy dresses classy, sporty dresses sporty (just think of the Spice Girls, style goes with type)... a mismatched style makes you weirdly uncomfortable and it shows *pretends tie is noose*. Conversely, insofar you're not the mall-bland greyman-type, you can really make a statement by choosing an "alternative clothing"-style.)
Your fit (e.g. shoulder seam stops at the bone and not halfway down the delts, etc. Fit essentially comes down to the "panels" of the clothing matching the "panels" of YOUR body. Ideally highlighting the good ones and hiding the bad ones (again YOUR body). Note that more expensive clothes have more "panels" and thus the potential to create a greater fit. For example, fancy t-shirts make 30" biceps look bigger than they really are, cheap t-shirts do the bare minimum towards the average 36" waist.)
Your colors (you probably look better in some colors than others whereas for idiosyncratic reasons, your entire wardrobe is blue because you just keep propagating blue whenever you buy new stuff even if you look better in grey; there are also warm colors and cold colors and what works for you depends on your skin tone/eyes/hair---the right "heat" is an instant improvement over the wrong "heat" for imperceptible reasons.)
Their patterns (there are "rules" but it's hard to go wrong with "simpler is better". If in doubt, avoid complications.)
Their texture (same thing).
... fog of war ...
Like with any system, it's possible to either not understand or care about it at all or alternatively go as deep as the rabbit hole goes. However, I do have some confidence in the order above in terms of getting dressed. Personally, I'm somewhere between 3 and 4 in this [Wheaton scale] list.
Possible theme for an ERE meetup/workshop: "How to dress well". It would likely help to bring along an expert of sorts. Does anyone have connections to a stylist? Might this be a thing?
I think there can be some risk/expense in consulting a stylist if/when your own Wheaton Level is still very low. "Stick to the classics" is a rule for newbies for the same reason that "Stick to an index fund" is a rule for newbies. Obviously, this realm is much like Interior Design/Decor or Ornamental Garden Design, so skill sets will often transfer.
Step 2:Style can go very deep and it will often make more sense to see aspects of 3) 4) 5) 6) as being subsidiary to 2). Analogous to how you would have to be fairly advanced in cooking skills before you could separate the spices generally associated with a cuisine from that cuisine. Also, if the goal is to be stylish and authentic, one tip would be to choose a style icon or set of icons with whom you share some physical features or personality attributes you would like to convey, but then adjust for your likely to be less fancy lifestyle. However, important note would be that style icon who best matches your physical type/coloring (okay if somewhat aspirational) is best for most choices and style icon who matches your personality (especially if aspirational) would be better kept to accent notes or accessories.
@7wb5 - Yes, if this was ever to happen, it would be optimal to find a stylist who is WL+1 ("inspiring") lest their solution be temporary. A good teacher-stylist who be able to adapt to the individual levels of each student.