We use to wear rugged boots, now it's all tailored suits

from A$AP Rocky (Ft. Santigold) – Hell Lyrics on Rap Genius

Meaning

Rocky’s rags-to-riches ride is the major theme of this album

He went from rocking Timbs and looking like a hoodlum to wearing suits like an executive. As you said this paints Rocky’s rags to riches.

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