I have been wearing this outfit for years. It will never go out of style. Blue jeans, brown boots, white shirt and navy blazer. I think the white lace top cancels out the cowgirl feel. I always feel girly in white lace.
I really like plaid shirts in fall, but also like them "girlified" a bit, so I don't look like I'm just borrowing by husband's clothes. This more feminine look with skinny jeans, or even the right leggings is really cute, and my kind of comfy fall style.