Not anyone, only those lucky enough to have sufficient inherent attractiveness to outshine anything they could put on. When those have established a new aesthetic (either top-down/haute, or bottom-up/street), the industry comes in and skillfully polishes away the rough edges so that the basic idea can also work on the less fortunate, who will then for a brief period be able to enjoy a "pretty by association" halo effect.

Sceptics sometimes consider the fashion lifecycle to be some kind of artificial conspiracy made up by the industry to create demand, but I think it is more an emergent phenomenon of human interaction that could only ever be subdued by extreme scarcity or by draconian regulation (e.g. rules applying to lower classes in many feudal society).

Are those prices in USD? Surely if you're deliberately trying to look shit you don't spend $1,000 on each piece of clothing to do so...

When/where/by whom are those meant to be worn, who receives the signal, and what is the intended effect?