The check shirt is probably the most forgiving casual shirt a man can own because the pattern does a lot of work to make even relatively simple outfits look like you thought about them. A flannel check in autumn earth tones with straight jeans and desert boots is the kind of look that requires genuinely almost no effort while appearing quite considered. We’ve found that the scale of the check matters more than most men realise. A small tight check reads more formally and works better in smarter casual situations. A larger bolder check is more casual and more expressive. A classic gingham sits comfortably in the middle ground. Keep everything else relatively neutral when you’re wearing a check because the pattern is already providing the visual interest and competing with it tends to result in something that looks busy rather than considered.