Without the hole punching on the toe I think jeans would be fine. However, as they are sold in stores, I think Weymouths are too .... something .... fancy? .... for jeans. With suits, trousers, et cetera, no problem.
I think it depends on the style of the shoe. Polo RL, for example, recently offered a brown chelsea boot with a floating medallion (term stolen from Jcusey!
on the toe - if I saw it in my size, I would've bought a pair to wear with jeans and dress shirts. Barrett have a similar - but much further out of my price range - boot. The Weymouths are probably too dressy for jeans, but I guess you'll never know until you try. I'm thinking a very hip pair of boot-cut, dark distressed jeans could work - something 'sophisticated', but not some old faded 501s - more 'workwear'.