The darker shade may make it harder to pair or differentiate it from navy, the other reason I leaned towards the second one is that if the bottom one isn't as heavy or thick as the herringbone, you may be able to wear it much more often than the first one.
EDIT: Actually I just saw that the jacket you want is a tweed so in terms of versatiity outside of fall and winter that's out of the picture, IF you want fall/winter weight jacket then still go with the second one, if you want something to wear year round, then go with the
Thompson two-button jacket, although it is not as thick and a couple of more bucks it is still a Wool Jacket but at least you have the option of it being more a 4 season jacket and you can later purchase the pants to make it a suit.
Just read your line about wearing it with jeans, if that's the case go with the navy Thompson.