If you look at Bob around the years '65-'66, he was affecting a mode sort of style which cufflinks might have gone very well with. Check out the album cover of "Bringing It All Back Home" for an example of the general look I am speaking of, and check out a lot of pictures taken of him in 65-66. He was not doing the rustic look in work shirts and jeans then, not doing the acoustic blues-man look or the cowboy-hobo look or the serious ascetic working-class look (like in '63), he was doing more of an uptown rocker look, almost like a young Byron gone electric....fancy shirts in bright colors and patterns, groovy Beatle boots, scarves, stylish black leather jackets...cufflinks would have been perfect on him then.