I seem to recall TRS having a pretty well-defined cuff on dark denim, presumably USA-imported 501s, teamed with the classic colour of desert boot, a dark green polo shirt and a pink seersucker jacket.  Now, had he cuffed them himself or were they tailored?  Only the man himself would know.  With my old Bean, I went for a minimalist turn-up done by a seamstress - which probably cost me more than the jeans themselves.