I like the second shirt as well. Sure, it is very lumberjacky, but if you're going to wear a flannel shirt, might as well go all out. I have an old Eddie Bauer shirt that looks similar.I like no 2 and actually have an LL Bean chamois shirt in that pattern (lumberjack connotation nonwithstanding), but none of these can really be dressed up. The only way you can dress up flannel is if you're talking about flannel dress pants or a flannel blazer (solid colors on both).
Yea, dressed up was probably the wrong word. I pretty much meant what you said in what would go with the most outfits.I like the second shirt as well. Sure, it is very lumberjacky, but if you're going to wear a flannel shirt, might as well go all out. I have an old Eddie Bauer shirt that looks similar.
I agree that the notion of "dressing up" a flannel shirt can cause brain strain. Nonetheless, I responded to the OP's question yesterday because I figured that he might have been wondering which shirt would go best with chinos and loafers in addition to jeans and Bean boots. I didn't dwell on the matter, though--I did the best I could with the choices the OP gave me. What he does with our collective replies is his business now.
Back in the '70s and early '80s, when I was in high school and, then, college and when teachers and professors still dressed up, but in an academic style, a flannel shirt, knit tie and corduroy jacket (or, even, corduroy suit) was a fall and winter staple for some.On casual Fridays, I like to wear a knit tie with a flannel shirt. It looks quite good. I tend to use knit wool ties, but knit silks work also as long as they do not look shiny or refined.