Jeans & Boots: Opinions?

[JABacchetta]

I'm trying to venture out from my typical $40 pair of jeans and a pair of running shoes.

I picked up two pairs of AG jeans the other day, one relaxed fit (seen here), and one straight leg (seen here).

Now I'm looking for a pair of boots to go along with them. From what I've been reading, brown boots are preferred with jeans. From the online photos, I'm really liking this pair of Timberland Earthkeepers (seen here), but had a couple of questions:

1. Does that boot color go well with both of the jeans I chose?

2. Does the boot go well with a more dressed up jean look (i.e. sport coat)?

3. Would the boot be too dressy for a very casual jean look (i.e. white t-shirt)?

 

[johng70]

The linked boot will go well with dark jeans. Probably with the first pair of jeans as well.
Fine for casual.
As for the whole sport coat / jean / boot combo - that's a big NO from me. I'm not a big fan of the sportcoat and jean combo in any instance. But, the boots in question are definitely a casual boot style (big, round toe) - it should not be work with a sport coat or chinos in my opinion. It's a nice looking casual boot not a dress boot.