I also struggle with how to wear checks. I'm partial to a nice checked shirt but I'll be honest, I have absolutely no idea how to wear one and make it look stylish. They always make me feel a bit like a cowboy or a lumberjack - definitely masculine. Suppose I don't really help myself as jeans and boots are not exactly the most feminine things to pair it with. But this shirt is flannel and just so soft and cosy: it demands to be worn on days when there's a chill in the air and rain is threatening to appear.
As it turned out, the rain stayed away but we had wind. Lots of wind, hence my appearance in the below photo. Impromptu outdoor photography (ie wedging the camera in a tree branch) needs to reserved for calmer days methinks. However it did result in a delightful picture of trees and sky when a particularly ferocious gust blew it off the branch and onto the ground!
Shirt - New Look
White vest & jeans - Primark
Boots - Evans
Jacket - George