Depends on how low-key the article of clothing is.
I end up wearing my beater palladiums and old army jacket 4 days a week because of the rain, personally. It's just become part of my style at this point, fits my aesthetic well enough that it doesn't bother me.
As for rotating out pieces, that's perfectly fine.
Also keep in mind that no matter how much thought you put into your outfit, most people will never notice that you wore the same undershirt or jeans twice in a row. People's eyes go straight to jackets and shoes.